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Chloramphenicol is an antibiotic useful for the treatment of a number of bacterial infections.
Common side effects include bone marrow suppression, nausea, and diarrhea.
Chloramphenicol was discovered after being isolated from Streptomyces venezuelae in 1947.
1 Medical uses
2 Adverse effects
2.1 Aplastic anemia
2.2 Bone marrow suppression
2.4 Gray baby syndrome
2.5 Hypersensitivity reactions
2.6 Neurotoxic reactions
3.1 Use in special populations
3.2 Dose monitoring
3.3 Drug interactions
3.4 Drug antagonistic
4 Mechanism of action
6 Society and culture
6.3.3 Eye drops
7 Veterinary uses
9 Further reading
10 External links
The original indication of chloramphenicol was in the treatment of typhoid, but the now almost universal presence of multiple drug-resistant Salmonella typhi has meant it is seldom used for this indication except when the organism is known to be sensitive.
In low-income countries, the WHO no longer recommends oily chloramphenicol as first-line to treat meningitis, but recognises it may be used with caution if there are no available alternatives.
In the context of preventing endophthalmitis, a complication of cataract surgery, a 2017 systematic review found moderate evidence that using chloramphenicol eye drops in addition to an antibiotic injection ( cefuroxime or penicillin ) will likely lower the risk of endophthalmitis, compared to eye drops or antibiotic injections alone.
Chloramphenicol has a broad spectrum of activity and has been effective in treating ocular infections such as conjunctivitis, blepharitis etc. caused by a number of bacteria including Staphylococcus aureus, Streptococcus pneumoniae, and Escherichia coli. It is not effective against Pseudomonas aeruginosa. The following susceptibility data represent the minimum inhibitory concentration for a few medically significant organisms.
Escherichia coli : 0.015 – 10,000 μg/mL
Staphylococcus aureus : 0.06 – 128 μg/mL
Streptococcus pneumoniae : 2 – 16 μg/mL
Each of these concentrations is dependent upon the bacterial strain being targeted. Some strains of E. coli, for example, show spontaneous emergence of chloramphenicol resistance.
Three mechanisms of resistance to chloramphenicol are known: reduced membrane permeability, mutation of the 50S ribosomal subunit, and elaboration of chloramphenicol acetyltransferase. It is easy to select for reduced membrane permeability to chloramphenicol in vitro by serial passage of bacteria, and this is the most common mechanism of low-level chloramphenicol resistance. High-level resistance is conferred by the cat -gene; this gene codes for an enzyme called chloramphenicol acetyltransferase, which inactivates chloramphenicol by covalently linking one or two acetyl groups, derived from acetyl- S -coenzyme A, to the hydroxyl groups on the chloramphenicol molecule. The acetylation prevents chloramphenicol from binding to the ribosome. Resistance-conferring mutations of the 50S ribosomal subunit are rare.
Chloramphenicol resistance may be carried on a plasmid that also codes for resistance to other drugs. One example is the ACCoT plasmid (A= ampicillin, C=chloramphenicol, Co= co-trimoxazole, T= tetracycline ), which mediates multiple drug resistance in typhoid (also called R factors ).
As of 2014 some Enterococcus faecium and Pseudomonas aeruginosa strains are resistant to chloramphenicol. Some Veillonella spp. and Staphylococcus capitis strains have also developed resistance to chloramphenicol to varying degrees.
The most serious side effect of chloramphenicol treatment is aplastic anaemia. This effect is rare and sometimes fatal. The risk of AA is high enough that alternatives should be strongly considered. Treatments are available but expensive. No way exists to predict who may or may not get this side effect. The effect usually occurs weeks or months after treatment has been stopped, and a genetic predisposition may be involved. It is not known whether monitoring the blood counts of patients can prevent the development of aplastic anaemia, but patients are recommended to have a baseline blood count with a repeat blood count every few days while on treatment.
Thiamphenicol, a related compound with a similar spectrum of activity, is available in Italy and China for human use, and has never been associated with aplastic anaemia. Thiamphenicol is available in the U.S. and Europe as a veterinary antibiotic, but is not approved for use in humans.
Bone marrow suppression
Chloramphenicol may cause bone marrow suppression during treatment; this is a direct toxic effect of the drug on human mitochondria.
Leukemia, a cancer of the blood or bone marrow, is characterized by an abnormal increase of immature white blood cells. The risk of childhood leukemia is increased, as demonstrated in a Chinese case–control study, and the risk increases with length of treatment.
Gray baby syndrome
Intravenous chloramphenicol use has been associated with the so-called gray baby syndrome.
This phenomenon occurs in newborn infants because they do not yet have fully functional liver enzymes (i.e. UDP-glucuronyl transferase), so chloramphenicol remains unmetabolized in the body.
This causes several adverse effects, including hypotension and cyanosis. The condition can be prevented by using the drug at the recommended doses, and monitoring blood levels.
Fever, macular and vesicular rashes, angioedema, urticaria, and anaphylaxis may occur. Herxheimer’s reactions have occurred during therapy for typhoid fever.
Headache, mild depression, mental confusion, and delirium have been described in patients receiving chloramphenicol. Optic and peripheral neuritis have been reported, usually following long-term therapy. If this occurs, the drug should be promptly withdrawn.
Chloramphenicol is extremely lipid-soluble; it remains relatively unbound to protein and is a small molecule. It has a large apparent volume of distribution and penetrates effectively into all tissues of the body, including the brain. Distribution is not uniform, with highest concentrations found in the liver and kidney, with lowest in the brain and cerebrospinal fluid. The concentration achieved in brain and cerebrospinal fluid is around 30 to 50% of the overall average body concentration, even when the meninges are not inflamed; this increases to as high as 89% when the meninges are inflamed.
Chloramphenicol increases the absorption of iron.
Use in special populations
Chloramphenicol is metabolized by the liver to chloramphenicol glucuronate (which is inactive). In liver impairment, the dose of chloramphenicol must therefore be reduced. No standard dose reduction exists for chloramphenicol in liver impairment, and the dose should be adjusted according to measured plasma concentrations.
The majority of the chloramphenicol dose is excreted by the kidneys as the inactive metabolite, chloramphenicol glucuronate. Only a tiny fraction of the chloramphenicol is excreted by the kidneys unchanged. Plasma levels should be monitored in patients with renal impairment, but this is not mandatory. Chloramphenicol succinate ester (an intravenous prodrug form) is readily excreted unchanged by the kidneys, more so than chloramphenicol base, and this is the major reason why levels of chloramphenicol in the blood are much lower when given intravenously than orally.
Chloramphenicol passes into breast milk, so should therefore be avoided during breast feeding, if possible.
Plasma levels of chloramphenicol must be monitored in neonates and patients with abnormal liver function. Plasma levels should be monitored in all children under the age of four, the elderly, and patients with renal failure.
Because efficacy and toxicity of chloramphenicol are associated with a maximum serum concentration, peak levels (one hour after the intravenous dose is given) should be 10–20 µg/ml with toxicity > 40 µg/ml ; trough levels (taken immediately before a dose) should be 5–10 µg/ml.
Administration of chloramphenicol concomitantly with bone marrow depressant drugs is contraindicated, although concerns over aplastic anaemia associated with ocular chloramphenicol have largely been discounted.
Chloramphenicol is a potent inhibitor of the cytochrome P450 isoforms CYP2C19 and CYP3A4 in the liver.
Chloramphenicol is antagonistic with most cephalosporins and using both together should be avoided in the treatment of infections.
Mechanism of action
Chloramphenicol is a bacteriostatic by inhibiting protein synthesis. It prevents protein chain elongation by inhibiting the peptidyl transferase activity of the bacterial ribosome. It specifically binds to A2451 and A2452 residues
Chloramphenicol was first isolated from Streptomyces venezuelae in 1947 and in 1949 a team of scientists at Parke-Davis including Mildred Rebstock published their identification of the chemical structure and their synthesis, making it the first antibiotic to be made instead of extracted from a micro-organism.
In 2007, the accumulation of reports associating aplastic anemia and blood dyscrasia with chloramphenicol eye drops lead to the classification of “probable human carcinogen” according to World Health Organization criteria, based on the known published case reports and the spontaneous reports submitted to the National Registry of Drug-Induced Ocular Side Effects.
Society and culture
In many areas of the world an intravenous dose is about US$0.40–1.90. In the United States it costs about $3.60 per dose in oral tablet form at wholesale.
Chloramphenicol is available as a generic worldwide under many brandnames
Chloramphenicol is available as a capsule or as a liquid. In some countries, it is sold as chloramphenicol palmitate ester (CPE). CPE is inactive, and is hydrolysed to active chloramphenicol in the small intestine. No difference in bioavailability is noted between chloramphenicol and CPE.
Manufacture of oral chloramphenicol in the U.S. stopped in 1991, because the vast majority of chloramphenicol-associated cases of aplastic anaemia are associated with the oral preparation. No oral formulation of chloramphenicol is now available in the U.S.
In molecular biology, chloramphenicol is prepared in ethanol.
The intravenous (IV) preparation of chloramphenicol is the succinate ester, because pure chloramphenicol does not dissolve in water. This creates a problem: Chloramphenicol succinate ester is an inactive prodrug and must first be hydrolysed to chloramphenicol; however, the hydrolysis process is often incomplete, and 30% of the dose is lost and removed in the urine. Serum concentrations of IV chloramphenicol are only 70% of those achieved when chloramphenicol is given orally.
Oily chloramphenicol (or chloramphenicol oil suspension) is a long-acting preparation of chloramphenicol first introduced by Roussel in 1954; marketed as Tifomycine, it was originally used as a treatment for typhoid. Roussel stopped production of oily chloramphenicol in 1995; the International Dispensary Association has manufactured it since 1998, first in Malta and then in India from December 2004.
Oily chloramphenicol was first used to treat meningitis in 1975
Chloramphenicol is still used occasionally in topical preparations ( ointments and eye drops ) for the treatment of bacterial conjunctivitis. Isolated case reports of aplastic anaemia following use of chloramphenicol eyedrops exist, but the risk is estimated to be of the order of less than one in 224,716 prescriptions. In Mexico, this is the treatment used prophylactically in newborns.
Although its use in veterinary medicine is highly restricted, chloramphenicol still has some important veterinary uses.
Although unpublished, recent research suggests chloramphenicol could also be applied to frogs to prevent their widespread destruction from fungal infections. Chytridiomycosis is a fungal disease, blamed for the extinction of one-third of the 120 frog species lost since 1980.
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Levaquin is the brand name for levofloxacin, a prescription antibiotic drug used to treat a variety of bacterial infections, such as: Pneumonia Acute bacterial sinusitis Chronic bronchitis worsened by bacterial infections Skin infections Chronic prostate gland infection (prostatitis) Urinary tract infection (UTI) Acute kidney infection Inhalational anthrax, or anthrax contracted by breathing in anthrax spores Pneumonic and septicemic plague (Levaquin is also used to prevent contracting plague ) Levaquin belongs to a class of antibacterial agents called fluoroquinolones, which kill bacteria by inhibiting the activity of certain enzymes bacteria require to replicate, transcribe, repair, and recombine DNA.
Doctors may also prescribe Levaquin “off-label” to treat or prevent other bacterial infections, including tuberculosis (TB), Salmonella food poisoning, Shigella food poisoning, Campylobacter infections, and disseminated Mycobacterium avium complex disease, especially for people with a weakened immune system from HIV or other conditions.
Levaquin was first approved by the Food and Drug Administration (FDA) in 1996, and is produced by Janssen Pharmaceuticals, Inc, a subsidiary of Johnson & Johnson.
Levaquin and Tendon Issues In 2008, the FDA required all fluoroquinolone manufacturers to include a black-box warning that the drug class can increase a person’s risk of tendonitis (tendon inflammation) and tendon rupture, a decision that came too late for a lot of people taking Levaquin, resulting in numerous lawsuits.
Plaintiffs charge that Johnson & Johnson should have strengthened their warnings about the potential tendon issues associated with Levaquin before the FDA issued its decree, and also that the company downplayed the drug’s risks to boost sales.
In 2010, Johnson & Johnson lost a court case against 87-year-old John Schedin, and had to pay nearly $2 million to Schedin for the damage he received to his Achilles tendon after taking Levaquin.
The company subsequently won several other court cases, in which plaintiffs failed to show the drug caused their tendon issues.
To date, however, thousands more cases have reached settlements out of court.
The risk of tendonitis and tendon ruptures is greater for people over 60 years old, people taking corticosteroid drugs, and people with kidney, heart, or lung transplants.
Physical activity or exercise, kidney failure, and having previous tendon problems, such as rheumatoid arthritis, can also increase your risk of tendon issues while taking Levaquin.
Levaquin Warnings You should not take Levaquin if you have a known sensitivity or allergy to levofloxacin and other quinolones (the family of antibiotics that encompasses fluoroquinolones).
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Levofloxacin is presumed to be present in breast milk, and the drug has the potential to cause serious side effects in infants.
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BasicDescription Back to Top Levaquin Side Effects Common Side Effects of Levaquin The most common side effects of Levaquin are: Nausea Headache Diarrhea Insomnia Constipation Dizziness Other common side effects include yeast infections, vaginitis, severe itching, chest pain, and swelling from water buildup (edema).
Severe Side Effects of Levaquin Though rare, Levaquin can result in numerous serious side effects that may require medical attention, including: Central nervous system effects, including seizers, hallucinations, nightmares, depression, confusion, paranoia, suicidal thoughts, and tremors Gastrointestinal infections and disorders Potentially irreversible peripheral neuropathy (damage to the nerves outside the brain and spinal cord) Serious heart rhythm changes Joint problems Changes in blood sugar Sensitivity to sunlight Severe diarrhea from the difficult-to-treat bacteria Clostridium difficile Additionally, children taking Levaquin may develop musculoskeletal disorders, such as arthritis and gait abnormalities.
Back to Top Levaquin Interactions Levaquin may interact with: Antacids, multivitamins, and supplements containing magnesium, aluminum, iron, or zinc Sucralfate (Carafate) Didanosine (Videx) Warfarin (Coumadin, Jantoven) Antidiabetic medicine Non-steroidal anti-inflammatory drugs, including aspirin and ibuprofen Theophylline (Theo-24, Theolair) Make sure to tell your doctor about any medications, drugs, and supplements you take, especially steroid medications, anti-psychotic drugs, tricyclic antidepressants, diuretics, and heart-rate medications.
Levaquin and Other Interactions Levaquin may produce a false-positive urine test for opiates.
You should tell your doctor or other healthcare professional that you’re taking Levaquin when submitting a urine sample.
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Dosage and length of treatment differs depending on the type of infection that needs to be treated; adults with kidney problems, as well as children, must follow an adjusted treatment schedule.
Levaquin Overdose According to animal studies, Levaquin is toxic in high doses, causing a number of muscular and nervous system symptoms, such as tremors, convulsions, and loss of control of bodily movements.
Call your local poison control center or visit the nearest emergency hospital room if you’ve overdosed on Levaquin to have your stomach emptied.
Call 9-1-1 if you think someone has overdosed and has collapsed or isn’t breathing.
Missed Dose of Levaquin Take the missed dose as soon as you remember it, unless it’s almost time for next dose.
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Labetalol is a drug used to treat high blood pressure.
It’s also known by its brand names Normodyne and Trandate.
This medicine is in a group of drugs called beta blockers.
It works by relaxing blood vessels and slowing heart rate to improve blood flow and decrease blood pressure.
Labetalol is also sometimes used to treat chest pain and to treat people with tetanus.
The drug comes in a tablet and intravenous (IV) form.
Labetalol controls high blood pressure, but it does not cure it.
You should continue to take labetalol even if you feel well.
The drug is only part of a complete treatment program for high blood pressure that may also include diet, exercise, and weight control.
The Food and Drug Administration approved labetalol in 1984; the drug is manufactured by Prometheus Laboratories.
Labetalol Warnings You should not stop taking labetalol without talking to your doctor first.
If this drug is stopped suddenly, it may cause chest pain or heart attack in some people.
This medication may also make you drowsy, so you should not drive a car or operate machinery until you know how it will affect you.
Your blood pressure should be checked regularly to evaluate your response to labetalol.
You should also check your pulse periodically.
If your pulse rate is faster or slower than it should be, call your doctor.
Before taking labetalol, you should tell your doctor and pharmacist if you: Are allergic to it or another other drugs Have ever had heart, kidney, or liver disease; asthma or other lung disease; severe allergies ; diabetes, or pheochromocytoma (an adrenal gland tumor) Are pregnant, plan to become pregnant, or are breastfeeding Are having surgery, including dental surgery Labetalol and Pregnancy It’s not known whether labetalol will harm an unborn baby, though the drug has been linked to heart and lung problems in newborns.
Labetalol can pass into breast milk and may harm a breastfeeding baby.
BasicDescription Back to Top Labetalol Side Effects Common Side Effects of Labetalol Some side effects of labetalol may include: Excessive tiredness Tingling scalp or skin Dizziness Lightheadedness Upset stomach Stuffy nose Fatigue Serious Side Effects of Labetalol If you experience any of the following symptoms, call your doctor immediately: Swelling of the lower legs and feet Sudden weight change Shortness of breath or wheezing Chest pain Severe slow heart rate Back to Top Labetalol Interactions Patients who take diabetes medications to lower blood sugar (such as insulin or oral antidiabetic drugs) may need to monitor their blood sugar more frequently while taking labetalol.
Halothane anesthesia may contribute to the blood-pressure lowering effects of labetalol.
Combining labetalol with tricyclic antidepressants such as amitriptyline (Elavil, Endep), imipramine (Tofranil), or nortriptyline (Pamelor) may lead to an increase in tremor.
If combined with adrenergic-stimulating drugs used for treating asthma, such as albuterol (Proventil, Ventolin) or pirbuterol (Maxair), the effects of labetalol may counteract the effects of the stimulating drugs and reduce their effectiveness.
Cimetidine (Tagamet) may increase the effectiveness of labetalol by blocking its elimination and increasing its levels in the blood.
Less labetalol may be needed when cimetidine and labetalol are used together.
You should tell your doctor about all prescription, non-prescription, illegal, recreational, herbal, nutritional, or dietary drugs or supplements you are taking.
You can continue your normal diet and activities unless otherwise instructed by your doctor while taking labetalol.
However, consuming alcohol while on labetalol can make you drowsier.
Back to Top Labetalol Dosage The recommended starting oral dose of labetalol is 100 milligrams (mg), twice a day.
The dose can be increased by 100 mg twice daily, every two to three days based on your response.
Usual maintenance doses are 200-400 mg, twice daily.
People with very high blood pressure may require 1.2 to 2.4 grams daily.
The initial intravenous dose of the drug is 20 mg injected over two minutes.
Additional injections of 40 or 80 mg may be given every 10 minutes as needed up to a total dose of 300 mg.
The medicine may also be given by intravenous infusion at 1 to 2 milligrams/minute.
Labetalol Overdose If you suspect an overdose, you should contact a poison control center or emergency room immediately.
You can get in touch with a poison control center at (800) 222-1222.
Missed Dose of Labetalol If you miss a dose of labetalol, take it as soon as you remember.
However, if it is almost time for the next dose, skip the missed dose and continue to follow your regular dosing schedule.
Do not double up on doses.
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Levothyroxine is a synthetic thyroid hormone used to treat hypothyroidism, a condition in which the thyroid gland doesn’t produce enough thyroid hormone.
The drug is available under the brand names Levothroid, Levoxyl, Levo-T, Synthroid, Tirosint, and Unithroid.
Thyroid hormones affect the metabolism of protein, fats, and carbohydrates.
They also affect a person’s growth and development.
If untreated, hypothyroidism can lead to poor growth, slow speech, loss of energy, weight gain, hair loss, dry skin, and increased sensitivity to cold temperatures.
Levothyroxine can help reverse these symptoms.
The drug can also help treat the congenital form of hypothyroidism, as well as an enlarged thyroid gland ( goiter ) and thyroid cancer.
Levothyroxine has been available in the United States since the 1950s, but the Food and Drug Administration (FDA) didn’t approve it until 2000.
Levothyroxine Warnings Thyroid hormone is not a treatment for obesity, and people with normal thyroid function should not take levothyroxine.
If you have a healthy thyroid and take levothyroxine, you could develop life-threatening side effects.
This is particularly true if you take the drug with amphetamines.
Although levothyroxine treats an underactive thyroid, it’s not a cure for the condition.
You should also understand that it may take several weeks before you see an improvement in your symptoms.
Women on long-term levothyroxine therapy may be at greater risk for osteoporosis.
Over time, the drug can lead to a decrease in bone mineral density.
A study published in 2014 in the Journal of Preventive Medicine & Public Health investigated the link between the risk for broken bones and levothyroxine use among older women with underactive thyroids.
The researchers concluded that doctors should be particularly concerned about the overuse of levothyroxine in older women with osteoporosis.
Before taking levothyroxine, tell your doctor if you’ve ever had: Diabetes Heart disease, such as atherosclerosis (“hardening of the arteries”) High blood pressure Chest pain ( angina ) Irregular heartbeat Heart attack Kidney disease Hepatitis Underactive adrenal or pituitary gland Blood-clotting disorders Let your doctor know if you have any type of surgery planned.
People with heart disease, or older people at greater risk for heart disease, may need a lower dose of levothyroxine.
Levothyroxine and Pregnancy Tell your doctor if you are pregnant, may become pregnant, or are breastfeeding before taking levothyroxine.
Research shows that it’s safe to take levothyroxine during pregnancy, though it’s likely your doctor will adjust your dose of levothyroxine during your pregnancy.
If you find out you have hypothyroidism during pregnancy, your doctor will probably treat the condition.
Also, women with underactive thyroid may need to take levothyroxine to ensure that they produce enough breast milk.
Because of this, doctors may vary the dosage for women who are breastfeeding It’s generally considered safe for children to take levothyroxine.
BasicDescription Back to Top Levothyroxine Side Effects Levothyroxine may cause side effects.
Some common ones include: Weight loss Tremor Headache Nausea Vomiting Diarrhea Stomach cramps Nervousness Irritability Insomnia Excessive sweating Increased appetite Fever Changes in menstrual cycle Sensitivity to heat Temporary hair loss, especially among children during the first month of treatment More serious side effects can also occur.
If you have any of these side effects, stop taking levothyroxine and get medical treatment right away: Chest pain Rapid or irregular heartbeat or pulse Back to Top Levothyroxine Interactions It’s very important to let your doctor know about all medications you are taking, including illegal drugs and any over-the-counter herbs or supplements.
Types of drugs that interact with levothyroxine include: Amphetamines Aspirin Blood thinners such as warfarin (Coumadin) Antidepressants or drugs used to treat anxiety Heart medications, such as metoprolol (Lopressor, Toprol), propranolol ( Inderal ), and digoxin (Lanoxin) Anti-seizure drugs such as phenytoin ( Dilantin ) Estrogens and oral contraceptives Diabetes medications, including insulin Other Interactions You should take levothyroxine on an empty stomach 30 to 60 minutes before breakfast.
Talk with your doctor about how certain foods could affect the absorption of the drug and your dosage of the medication.
Back to Top Levothyroxine Dosage Levothyroxine comes as a tablet you take by mouth.
Take it with a full glass of water.
When giving levothyroxine to an infant or child, you can crush the tablet and mix it in 1 to 2 teaspoons of water.
Don’t mix the medication with food or soybean infant formula.
Use this mixture right away.
Your dosage of levothyroxine depends on many variables, including: Your age Your weight The severity of your condition Other health problems you may have Other medications you are taking When prescribing levothyroxine, your doctor will need to find the right balance.
If your dose is too strong, your thyroid levels will get too high, which can lead to heart problems and bone loss.
Your doctor will probably start you on a low dose of levothyroxine and gradually increase it until your thyroid level is within a normal range.
Once your doctor finds the right dose of medication for you, you won’t need to go to the doctor as frequently.
Your dose will likely remain the same for years unless you become pregnant, develop heart disease, or begin hormone replacement therapy.
Levothyroxine Overdose You shouldn’t take more levothyroxine than your doctor prescribes.
If you take too much of the drug, you may develop symptoms of overactive thyroid, including fatigue, sensitivity to heat, increased appetite, and sweating.
Symptoms of a levothyroxine overdose may also include: Confusion and disorientation Shock Coma Death If you or someone else has symptoms of an overdose, call a poison control center at 800-222-1222.
If someone collapses or isn’t breathing, call 911.
Missed Dose of Levothyroxine It’s important not to skip doses of levothyroxine.
If you accidentally miss a dose, take the missed dose as soon as you remember it.
If it’s almost time for your next regular dose, however, skip the missed dose.
Don’t take twice as much levothyroxine at one time to make up for a missed dose.
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Bicalutamide, sold under the brand name Casodex among others, is an antiandrogen medication that is primarily used to treat prostate cancer.
Common side effects in men include breast enlargement, breast tenderness, and hot flashes.
Bicalutamide is a member of the nonsteroidal antiandrogen (NSAA) group of medications.
Bicalutamide was patented in 1982 and approved for medical use in 1995.
1 Medical uses
1.1 Available forms
3 Side effects
6.1.1 Antiandrogenic activity
6.1.2 Other activities
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Cost and generics
9.4 Sales and usage
11 Veterinary use
12 See also
14 Further reading
15 External links
Main article: Medical uses of bicalutamide
Bicalutamide is approved for and mainly used in the following indications:
Metastatic prostate cancer (mPC) in men in combination with a gonadotropin-releasing hormone (GnRH) analogue or surgical castration at moderate doses
Locally advanced prostate cancer (LAPC) in men as a monotherapy in high doses
It can also be and is used to a lesser extent for the following off-label (non-approved) indications:
To reduce the effects of the testosterone flare at the initiation of GnRH agonist therapy in men
Androgen-dependent skin and hair conditions such as acne, seborrhea, excessive hair growth, and scalp hair loss in women at low doses, generally in combination with a birth control pill
High testosterone levels such as due to polycystic ovary syndrome (PCOS) in women
Feminizing hormone therapy for transgender women in combination with an estrogen
Early puberty in boys in moderate doses, especially for gonadotropin-independent early puberty
Overly long-lasting erections in men at low to very low doses
It has been suggested for but has uncertain effectiveness in the following indications:
Hypersexuality and paraphilias, particularly in combination with chemical castration
For more information on these uses, see the medical uses of bicalutamide article.
Bicalutamide is available for the treatment of prostate cancer in most developed countries,
Bicalutamide is pregnancy category X, or “contraindicated in pregnancy”, in the U.S.,
In individuals with severe, though not mild-to-moderate hepatic impairment, there is evidence that the elimination of bicalutamide is slowed, and hence, caution may be warranted in these patients as circulating levels of bicalutamide may be increased.
Main article: Side effects of bicalutamide
v t e Major side effects of bicalutamide alone
Very common (≥10%)
Reproductive system and breast disorders
• Breast tenderness a • Gynecomastia a
Common (≥1% and <10%) General and psychiatric disorders • Asthenia • Decreased libido • Erectile dysfunction • Hot flashes Skin and subcutaneous tissue disorders • Decreased body hair Hepato-biliary disorders • Elevated liver enzymes b Uncommon (≥0.1% and <1%) Immune system disorders • Hypersensitivity reactions, including angioedema and hives Rare (<0.1%) and unknown Respiratory, thoracic, and mediastinal disorders • Interstitial lung disease c Skin and subcutaneous tissue disorders • Sensitivity to light Hepato-biliary disorders • Liver toxicity d Footnotes and sources a = Incidence of breast changes of up to 80 to 90%. Mild-to-moderate in 90% of cases. Incidence greatly decreased in combination with castration. b = Elevated liver enzymes rarely severe and usually transient, resolving or improving with continued therapy or with discontinuation. Incidence of 3.4% relative to 1.9% for placebo in a high-dose (150 mg/day) 4,000-patient trial. c = Six case reports of interstitial lung disease published (as of 2016). Incidence of 0.01% (12 patients) in an 87,000-patient cohort. d = Six case reports of hepatotoxicity published (as of 2018). No cases in a high-dose (150 mg/day) 4,000-patient trial (suggesting incidence of <0.03%). Sources: The side effect profile of bicalutamide is highly dependent on sex; that is, on whether the person is male or female. In men, due to androgen deprivation, a variety of side effects of varying severity may occur during bicalutamide treatment, with breast pain/tenderness and gynecomastia ( breast development / enlargement ) being the most common. Bicalutamide monotherapy has been associated with abnormal liver function tests such as elevated liver enzymes in 3.4% of men relative to 1.9% for standard care. A total of 6 cases of hepatotoxicity or liver failure, two of which resulted in death, have been reported in association with bicalutamide. Comparison See also: Comparison of bicalutamide with other antiandrogens The side effect profile of bicalutamide in men and women differs from that of other antiandrogens and is considered favorable in comparison. Bicalutamide does not share the high risk of neuropsychiatric side effects like depression, anxiety, and suicidality as well as cardiovascular side effects like coagulation changes, thrombosis, fluid retention, ischemic cardiomyopathy, and adverse serum lipid changes that CPA is associated with. Overdose A single oral dose of bicalutamide in humans that results in symptoms of overdose or that is considered to be life-threatening has not been established. Interactions Bicalutamide is almost exclusively metabolized by CYP3A4. Because bicalutamide circulates at relatively high concentrations and is highly protein-bound, it has the potential to displace other highly protein-bound drugs like warfarin, phenytoin, theophylline, and aspirin from plasma binding proteins. Pharmacology Main article: Pharmacology of bicalutamide Pharmacodynamics Antiandrogenic activity Bicalutamide acts as a highly selective competitive silent antagonist of the AR ( IC 50 = 159–243 nM), the major biological target of the androgen sex hormones testosterone and DHT, and hence is an antiandrogen. The affinity of bicalutamide for the AR is relatively low as it is approximately 30 to 100 times lower than that of DHT, which is 2.5- to 10-fold as potent as an AR agonist as testosterone in bioassays and is the main endogenous ligand of the receptor in the prostate gland. Blockade of the AR by bicalutamide in the pituitary gland and hypothalamus results in prevention of the negative feedback of androgens on the hypothalamic–pituitary–gonadal axis (HPG axis) in males and consequent disinhibition of pituitary luteinizing hormone (LH) secretion. NSAA monotherapy, including with bicalutamide, shows a number of tolerability differences from methods of androgen deprivation therapy that incorporate surgical or medical castration. For example, the rates of hot flashes, depression, fatigue, and sexual dysfunction are all much higher with GnRH analogues than with NSAA monotherapy. It is thought that this is because GnRH analogues suppress estrogen production in addition to androgen production, resulting in estrogen deficiency. Under normal circumstances, bicalutamide has no capacity to activate the AR. In transgender women, breast development is a desired effect of antiandrogen or estrogen treatment. Bicalutamide monotherapy seems to have minimal effect on testicular spermatogenesis, testicular ultrastructure, and certain aspects of male fertility. Other activities Bicalutamide has been found to act as an inhibitor or inducer of certain cytochrome P450 enzymes including CYP3A4, CYP2C9, CYP2C19, and CYP2D6 in preclinical research, but no evidence of this has been found in humans treated with up to 150 mg/day. Pharmacokinetics Though its absolute bioavailability in humans is unknown, bicalutamide is known to be extensively and well- absorbed. The tissue distribution of bicalutamide is not well-characterized. Bicalutamide is metabolized in the liver. Bicalutamide is eliminated in similar proportions in feces (43%) and urine (34%), while its metabolites are eliminated roughly equally in urine and bile. The pharmacokinetics of bicalutamide are not affected by consumption of food, a person's age or body weight, renal impairment, or mild-to-moderate hepatic impairment. v t e Bicalutamide metabolism in humans Bicalutamide ( S )-Bicalutamide glucuronide ( R )-Hydroxybicalutamide ( R )-Hydroxybicalutamide glucuronide Glucuronidation via UGT1A9 Glucuronidation via UGT1A9 Hydroxylation via CYP3A4 This diagram illustrates the primary metabolic pathways involved in the metabolism of bicalutamide in humans. Chemistry Bicalutamide is a racemic mixture consisting of equal proportions of enantiomers ( R )-bicalutamide ( dextrorotatory ) and ( S )-bicalutamide ( levorotatory ). The acid dissociation constant (pKa') of bicalutamide is approximately 12. Bicalutamide is a synthetic and nonsteroidal compound which was derived from flutamide. Analogues See also: Discovery and development of antiandrogens First-generation NSAAs including bicalutamide, flutamide, and nilutamide are all synthetic, nonsteroidal anilide derivatives and structural analogues of each other. Chemical structures of first-generation NSAAs Flutamide Nilutamide Bicalutamide Topilutamide The second-generation NSAAs enzalutamide and apalutamide were derived from and are analogues of the first-generation NSAAs, Enzalutamide is a modification of bicalutamide in which the inter-ring linking chain has been altered and cyclized into a 5,5-di methyl -4- oxo -2- thioxo imidazolidine moiety. In apalutamide, the 5,5-dimethyl groups of the imidazolidine ring of enzalutamide are cyclized to form an accessory cyclobutane ring and one of its phenyl rings is replaced with a pyridine ring. Chemical structures of second-generation NSAAs Enzalutamide Apalutamide Proxalutamide Darolutamide The first nonsteroidal androgens, the arylpropionamides, were discovered via structural modification of bicalutamide. Chemical structures of arylpropionamide SARMs Acetothiolutamide Enobosarm Andarine A few radiolabeled derivatives of bicalutamide have been developed for potential use as radiotracers in medical imaging. 5 N -Bicalutamide, or 5-azabicalutamide, is a minor structural modification of bicalutamide which acts as a reversible covalent antagonist of the AR and has approximately 150-fold higher affinity for the AR and about 20-fold greater functional inhibition of the AR relative to bicalutamide. Synthesis A number of chemical syntheses of bicalutamide have been published in the literature. Bicalutamide synthesis Where the starting material is 4-cyano-3-(trifluoromethyl)aniline (also known as 4-amino-2-(trifluoromethyl)benzonitrile), DMA is dimethylacetamide, and m CPBA is meta -chloroperoxybenzoic acid. History Bicalutamide as well as all of the other currently marketed NSAAs were derived from structural modification of flutamide, which itself was originally synthesized as a bacteriostatic agent in 1967 at Schering Plough Corporation and was subsequently and serendipitously found to possess antiandrogenic activity. Bicalutamide was first studied in a phase I clinical trial in 1987 Following its introduction for use in combination with a GnRH analogue, bicalutamide was developed as a monotherapy at a dosage of 150 mg/day for the treatment of prostate cancer, and was approved for this indication in Europe, Canada, and a number of other countries in the late 1990s and early 2000s. Subsequent to negative findings of bicalutamide monotherapy for LPC in the EPC trial, approval of bicalutamide for use specifically in the treatment of LPC was withdrawn in a number of countries The patent protection of bicalutamide expired in the U.S. in March 2009 and the drug has subsequently been available as a generic, Bicalutamide was the fourth antiandrogen (and the third NSAA ) to be introduced for the treatment of prostate cancer, following the SAA CPA in 1973 Society and culture Generic names Bicalutamide is the generic name of the drug in English and French and its INN, USAN, USP, Brand names Bicalutamide is marketed by AstraZeneca in oral tablet form under the brand names Casodex, Cosudex, Calutide, Calumid, and Kalumid in many countries. Cost and generics Bicalutamide is off-patent and available as a generic, and its cost is low in comparison to a number of other similar medications (from US$10 to US$15.44 for a 30-day supply of once-daily 50 mg tablets). The patent protection of all three of the first-generation NSAAs has expired and flutamide and bicalutamide are both available as low-cost generics. Bicalutamide is considerably less costly than GnRH analogues, which, in spite of some having been off-patent many years, have been reported (in 2013) to typically cost US$10,000–$15,000 per year (or about US$1,000 per month) of treatment. Sales and usage Sales of bicalutamide (as Casodex) worldwide peaked at US$ 1.3 billion in 2007, Worldwide sales (millions, USD ) of Casodex, 1995–2017 Year Sales Year Sales Year Sales Year Sales Year Sales Year Sales Year Sales Year Sales 1995 ~$15m 1998 $245m 2001 $569m 2004 $1012m 2007 * $1335m 2010 $579m 2013 $376m 2016 $247m 1996 $109m 1999 $340m 2002 $644m 2005 $1123m 2008 $1258m 2011 $550m 2014 $320m 2017 $215m 1997 $200m 2000 $433m 2003 $854m 2006 $1206m 2009 $844m 2012 $454m 2015 $267m 2018 ND Total sales: $13.2 billion (as of end 2017). *: First generic availability. Between January 2007 and December 2009 (a period of three years), 1,232,143 prescriptions of bicalutamide were dispensed in the U.S., or about 400,000 prescriptions per year. Regulation Bicalutamide is a prescription drug. Research Bicalutamide has been studied in combination with the 5α-reductase inhibitors finasteride and dutasteride in prostate cancer. Bicalutamide has been studied in the treatment of benign prostatic hyperplasia (BPH) in a 24-week trial of 15 patients at a dosage of 50 mg/day. A phase III clinical trial of bicalutamide in combination with an ethinylestradiol -containing combined oral contraceptive for the treatment of severe hirsutism in women with PCOS was completed in Italy in 2017 under supervision of the Italian Agency for Drugs (AIFA). Veterinary use Bicalutamide may be used to treat hyperandrogenism and associated benign prostatic hyperplasia secondary to hyperadrenocorticism (caused by excessive adrenal androgens) in male ferrets. See also Comparison of bicalutamide with other antiandrogens
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Indapamide is a prescription medicine used to treat high blood pressure.
It’s also given to people who suffer from edema (fluid retention) due to congestive heart disease or another medical condition.
Indapamide is a diuretic (water pill) that works by helping the kidneys rid the body of unneeded water and salt.
The Food and Drug Administration (FDA) approved indapamide in 1983.
It’s manufactured by various pharmaceutical companies as a generic drug (no brand-name version is available).
Indapamide Warnings Before taking indapamide, tell your doctor if you have, or have ever had, any of the following: Diabetes Gout (a type of arthritis caused by a buildup of uric acid crystals in the joints) Any type of heart problem Kidney disease Liver disease Problems urinating Lupus (a chronic inflammatory condition) Thyroid or parathyroid disease Low levels of sodium or potassium in the blood Persistent vomiting A neurosurgical procedure known as a sympathectomy Allergies to any medication Indapamide may affect your blood sugar levels.
If you have diabetes, monitor your condition carefully while using this medicine.
Let your doctor know you’re taking indapamide before having any type of medical or dental procedure.
Also, tell your doctor if you’re currently on a low-salt diet.
Your doctor may recommend that you adopt a specific diet and exercise plan while taking indapamide.
Follow these instructions carefully.
Try to avoid becoming dehydrated while using indapamide.
Ask your doctor how much fluid you should consume throughout the day.
This medicine may make your skin more sensitive to sunlight.
Avoid unnecessary exposure to the sun and tanning booths, and wear sunscreen and protective clothing while outdoors.
Your doctor will want to perform frequent tests to check your body’s response to indapamide.
Keep all appointments with your doctor and laboratory.
Pregnancy and Indapamide Indapamide should only be taken during pregnancy when it’s clearly needed.
Tell your doctor if you become pregnant while using this medicine.
You’ll need to discuss the benefits and risks of taking indapamide during pregnancy.
It’s not known whether this drug passes into breast milk.
Don’t breastfeed a baby while using indapamide.
BasicDescription Back to Top Indapamide Side Effects Common Side Effects of Indapamide Tell your doctor if any of the following side effects become severe or don’t go away: Frequent urination (this symptom should decrease after a few weeks of treatment) Mild dizziness or lightheadedness (especially when standing or sitting up) Back pain Constipation Mild diarrhea Drowsiness Headache Nausea Runny nose Nervousness Trouble sleeping Upset stomach Weakness Vomiting Decreased sexual ability Serious Side Effects of Indapamide Tell your doctor right away if you experience any of the following serious side effects: Chest pain Blurred vision Jaundice Dark-colored urine Decreased urination or problems with urination Pale-colored stools Dry mouth Fainting Fast or irregular heartbeat Fatigue Fever, chills, cough, or sore throat Increased thirst Loss of appetite Numbness of the hands or feet Severe dizziness, drowsiness, or lightheadedness Severe stomach pain Red, swollen, peeling, or blistered skin Swelling of the hands, ankles, or feet Muscle pain, weakness, or cramping Confusion Mental or mood changes Seizures Unusual sluggishness, tiredness, or weakness Unusual bruising or bleeding Signs of anaphylaxis, which may include rash, hives, itching, difficulty breathing, chest tightness, or swelling of the face, mouth, lips, or tongue Back to Top Indapamide Interactions Tell your doctor about all prescription, nonprescription, illegal, recreational, herbal, nutritional, or dietary drugs you’re taking, especially: Other medication for high blood pressure Corticosteroids, such as prednisone Lanoxin ( digoxin ) Indocin ( indomethacin ) Lithobid ( lithium ) Benemid (probenecid) Vitamins Indapamide and Other Interactions Indapamide may make you drowsy.
Don’t drive or perform activities that require alertness until you know how this medicine affects you.
Indapamide and Alcohol Alcohol may worsen certain side effects of indapamide.
Avoid drinking alcoholic beverages while using this medicine.
Back to Top Indapamide Dosage Indapamide comes as a tablet to take by mouth, typically once daily in the morning.
Your dose will depend on your medical condition and response to treatment.
You can take this medicine with or without food.
At first, indapamide may make you urinate more often.
You may want to take your dose before 6 p.m.
to avoid disturbing your sleep with the need to urinate.
Follow the instructions on your prescription label carefully.
Don’t take more or less indapamide than is recommended.
Continue to take indapamide even if you feel well.
Don’t stop your treatment without first talking to your doctor.
Indapamide Overdose Symptoms of an indapamide overdose may include: Vomiting Nausea Weakness If you suspect an overdose, contact a poison control center or emergency room immediately.
You can get in touch with a poison control center at 800-222-1222.
Missed Dose of Indapamide If you miss a dose of indapamide, take it as soon as you remember.
But if it’s almost time for your next scheduled dose, skip the missed dose and continue with your regular medication schedule.
Don’t take extra medicine to make up for a missed dose.
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Sildenafil, sold as the brand name Viagra among others, is a medication used to treat erectile dysfunction and pulmonary arterial hypertension.
Common side effects include headaches, heartburn, and flushed skin.
Sildenafil acts by blocking phosphodiesterase 5 (PDE 5 ), an enzyme that promotes breakdown of cGMP, which regulates blood flow in the penis.
Pfizer originally discovered the medication in 1989 while looking for a treatment for heart related chest pain.
1 Medical uses
1.1 Sexual dysfunction
1.1.1 Antidepressant-associated sexual dysfunction
1.2 Pulmonary hypertension
1.3 Raynaud’s phenomenon
1.4 High-altitude pulmonary edema
2 Adverse effects
3 Nonmedical use
3.1 Recreational use
3.2 Jet lag research
4 Detection in biological fluids
5 Mechanism of action
6 Route of administration
7 Chemical synthesis
9 Society and culture
9.1 Marketing and sales
9.3 Regional issues
9.3.1 European Union
9.3.2 United Kingdom
9.3.3 United States
9.3.7 New Zealand
9.3.8 Other countries
11 External links
Pfizer Viagra tablet in the trademark blue diamond shape
The primary indication of sildenafil is treatment of erectile dysfunction (inability to sustain a satisfactory erection to complete intercourse). Its use is now one of the standard treatments for erectile dysfunction, including for men with diabetes mellitus.
Antidepressant-associated sexual dysfunction
Tentative evidence suggests that sildenafil may help men who experience antidepressant -induced erectile dysfunction.
While sildenafil improves some markers of disease in people with pulmonary arterial hypertension, it does not appear to affect the risk of death or serious side effects as of 2014
Sildenafil and other PDE5 inhibitors are used off-label to alleviate vasospasm and treat severe ischemia and ulcers in fingers and toes for people with secondary Raynaud’s phenomenon ;
High-altitude pulmonary edema
Sildenafil has been studied for high-altitude pulmonary edema but its use is currently not recommended for that indication.
In clinical trials, the most common adverse effects of sildenafil use included headache, flushing, indigestion, nasal congestion, and impaired vision, including photophobia and blurred vision.
Rare but serious adverse effects found through postmarketing surveillance include prolonged erections, severe low blood pressure, myocardial infarction (heart attack), ventricular arrhythmias, stroke, increased intraocular pressure, and sudden hearing loss.
Care should be exercised by people who are also taking protease inhibitors for the treatment of HIV infection. Protease inhibitors inhibit the metabolism of sildenafil, effectively multiplying the plasma levels of sildenafil, increasing the incidence and severity of side effects. Those using protease inhibitors are recommended to limit their use of sildenafil to no more than one 25 mg dose every 48 hours. Other drugs that interfere with the metabolism of sildenafil include erythromycin and cimetidine, both of which can also lead to prolonged plasma half-life levels.
The use of sildenafil and an α 1 blocker (typically prescribed for hypertension or for urologic conditions, such as benign prostatic hypertrophy ) at the same time may lead to low blood pressure, but this effect does not occur if they are taken at least 4 hours apart.
Contraindications include: : 11
Concomitant use of nitric oxide donors, organic nitrites and nitrates, such as:
alkyl nitrites (commonly known as ” poppers “)
Concomitant use of soluble guanylyl cyclase stimulators, such as riociguat
Known hypersensitivity to sildenafil
Sildenafil should not be used if sexual activity is inadvisable due to underlying cardiovascular risk factors
Sildenafil’s popularity with young adults has increased over the years.
Unprescribed recreational use of sildenafil and other PDE5 inhibitors is noted as particularly high among users of illegal drugs.
Jet lag research
The 2007 Ig Nobel Prize in Aviation went to Patricia V. Agostino, Santiago A. Plano, and Diego A. Golombek of Universidad Nacional de Quilmes, Argentina, for their discovery that sildenafil helps treat jet lag recovery in hamsters.
Professional athletes have been documented using sildenafil, believing the opening of their blood vessels will enrich their muscles. In turn, they believe it will enhance their performances.
Acetildenafil and other synthetic structural analogs of sildenafil which are PDE5 inhibitors have been found as adulterants in a number of “herbal” aphrodisiac products sold over-the-counter.
The US FDA has banned numerous products claiming to be Eurycoma longifolia that, in fact, contain only analogs of sildenafil. Sellers of such fake herbals typically respond by just changing the names of their products.
Detection in biological fluids
Sildenafil and/or N-desmethylsildenafil, its major active metabolite, may be quantified in plasma, serum, or whole blood to assess pharmacokinetic status in those receiving the drug therapeutically, to confirm the diagnosis in potential poisoning victims, or to assist in the forensic investigation in a case of fatal overdose.
Mechanism of action
Crystal structure of human PDE5 with bound sildenafil, PDB entry 1udt
Sildenafil protects cyclic guanosine monophosphate (cGMP) from degradation by cGMP-specific phosphodiesterase type 5 (PDE5) in the corpus cavernosum. Nitric oxide (NO) in the corpus cavernosum of the penis binds to guanylate cyclase receptors, which results in increased levels of cGMP, leading to smooth muscle relaxation ( vasodilation ) of the intimal cushions of the helicine arteries. This smooth muscle relaxation leads to vasodilation and increased inflow of blood into the spongy tissue of the penis, causing an erection. Robert F. Furchgott, Ferid Murad, and Louis Ignarro won the Nobel Prize in Physiology or Medicine in 1998 for their independent study of the metabolic pathway of nitric oxide in smooth muscle vasodilation.
Sildenafil is a potent and selective inhibitor of cGMP-specific phosphodiesterase type 5 (PDE5), which is responsible for degradation of cGMP in the corpus cavernosum. The molecular structure of sildenafil is similar to that of cGMP and acts as a competitive binding agent of PDE5 in the corpus cavernosum, resulting in more cGMP and better erections. Without sexual stimulation, and therefore lack of activation of the NO/cGMP system, sildenafil should not cause an erection. Other drugs that operate by the same mechanism include tadalafil (Cialis) and vardenafil (Levitra).
Sildenafil is broken down in the liver by hepatic metabolism using cytochrome p450 enzymes, mainly CYP450 3A4(major route), but also by CYP2C9 (minor route) hepatic isoenzymes. The major product of metabolisation by these enzymes is N-desmethylated sildenafil, which is metabolised further. This metabolite also has an affinity for the PDE receptors, about 40% of that of sildenafil. Thus, the metabolite is responsible for about 20% of sildenafil’s action. Sildenafil is excreted as metabolites predominantly in the feces (about 80% of administered oral dose) and to a lesser extent in the urine (around 13% of the administered oral dose). If taken with a high-fat meal, absorption is reduced; the time taken to reach the maximum plasma concentration increases by around one hour, and the maximum concentration itself is decreased by nearly one-third.
Route of administration
When taken by mouth sildenafil for erectile dysfunction results in an average time to onset of erections of 27 minutes (ranging from 12 to 70 minutes).
Under the tongue use of sildenafil for erectile dysfunction results in an average onset of action of 15 minutes and lasting for an average of 40 minutes.
There are also mouth spray preparations of sildenafil for faster onset of action.
The preparation steps for synthesis of sildenafil are:
Methylation of 3-propylpyrazole-5-carboxylic acid ethyl ester with hot dimethyl sulfate
Hydrolysis with aqueous sodium hydroxide (NaOH) to free acid
Nitration with oleum /fuming nitric acid
Carboxamide formation with refluxing thionyl chloride /NH 4 OH
Reduction of nitro group to amino group
Acylation with 2-ethoxybenzoyl chloride
Sulfonation to the chlorosulfonyl derivative
Condensation with 1-methylpiperazine.
Sildenafil (compound UK-92,480) was synthesized by a group of pharmaceutical chemists working at Pfizer’s Sandwich, Kent, research facility in England. It was initially studied for use in hypertension (high blood pressure) and angina pectoris (a symptom of ischaemic heart disease ). The first clinical trials were conducted in Morriston Hospital in Swansea.
Society and culture
Marketing and sales
Bulk bag of counterfeit Viagra
In the US even though sildenafil is available only by prescription from a doctor, it was advertised directly to consumers on TV (famously being endorsed by former United States Senator Bob Dole and football star Pelé ). Numerous sites on the Internet offer Viagra for sale after an “online consultation”, often a simple web questionnaire. The Viagra name has become so well known, many fake aphrodisiacs now call themselves ” herbal viagra ” or are presented as blue tablets imitating the shape and colour of Pfizer’s product. Viagra is also informally known as “vitamin V”, “the blue pill”, or “blue diamond”, as well as various other nicknames.
In 2000, Viagra sales accounted for 92% of the global market for prescribed erectile dysfunction pills.
In February 2007, it was announced that Boots, the UK pharmacy chain, would try over-the-counter sales of Viagra in stores in Manchester, England. Men between the ages of 30 and 65 would be eligible to buy four tablets after a consultation with a pharmacist. The decision was made, in part, to reduce online sales of counterfeit and potentially dangerous erectile dysfunction treatments.
On 6 May 2013, Pfizer, which manufactures Viagra, told the Associated Press they will begin selling the drug directly to patients on its website.
Pfizer’s patents on Viagra expired outside the US in 2012; in the US they were set to expire, but Pfizer settled litigation with each of Mylan and Teva which agreed that both companies could introduce generics in the US on 11 December 2017.
As of 2018, the U.S. Food and Drug Administration has approved 15 drug manufacturers to market generic sildenafil in the United States. Seven of these companies are based in India. This is likely to lead to dramatic price reductions.
Further information: Counterfeit medications
Counterfeit Viagra, despite generally being cheaper,
Viagra is one of the world’s most counterfeited medicines.
Pfizer’s patent on sildenafil citrate expired in some member countries of the EU, Austria, Denmark, France, Germany, Ireland, Italy, The Netherlands, Spain, Sweden, the United Kingdom and Switzerland on 21 June 2013.
There were 2,958,199 prescriptions for Sildenafil in 2016 in England, compared with 1,042,431 in 2006.
In 2018, Viagra Connect, a particular formulation of Sildenafil marketed by Pfizer, became available for sale without a prescription in the UK , in an attempt to widen availability and reduce demand for counterfeit products.
Sildenafil is available as a generic drug in the United States, labelled for pulmonary arterial hypertension.
In the United States, Pfizer received two patents for sildenafil: one for its indication to treat cardiovascular disease (marketed as Revatio) and another for its indication to treat erectile dysfunction (marketed as Viagra). The substance is the same under both trade names.
In 1992, Pfizer filed a patent covering the substance sildenafil and its use to treat cardiovascular diseases.
In 1994, Pfizer filed a patent covering the use of sildenafil to treat erectile dysfunction.
In Canada, Pfizer’s patent 2,324,324 for Revatio (sildenafil used to treat pulmonary hypertension) was found invalid by the Federal Court in June 2010, on an application by Ratiopharm Inc.
On 8 November 2012, the Supreme Court of Canada ruled that Pfizer’s patent 2,163,446 on Viagra was invalid from the beginning because the company did not provide full disclosure in its application. The decision, Teva Canada Ltd. v. Pfizer Canada Inc., pointed to section 27(3)(b) of The Patent Act which requires that disclosure must include sufficient information “to enable any person skilled in the art or science to which it pertains” to produce it. It added further: “As a matter of policy and sound statutory interpretation, patentees cannot be allowed to ‘game’ the system in this way. This, in my view, is the key issue in this appeal.”
Teva Canada launched Novo-Sildenafil, a generic version of Viagra, on the day the Supreme Court of Canada released its decision.
Manufacture and sale of sildenafil citrate drugs known as “generic Viagra” is common in India, where Pfizer’s patent claim does not apply. Trade names include Kamagra ( Ajanta Pharma ), Silagra ( Cipla ), Edegra ( Sun Pharmaceutical ), Penegra ( Zydus Cadila ), Manly (Cooper Pharma) and Zenegra ( Alkem Laboratories ).
Manufacture and sale of sildenafil citrate drugs is common in China, where Pfizer’s patent claim is not widely enforced.
Sildenafil was reclassified in New Zealand in 2014 so it could be bought over the counter from a pharmacist. It is thought that this reduced sales over the Internet and was safer as men could be referred for medical advice if appropriate.
Egypt approved Viagra for sale in 2002, but soon afterwards allowed local companies to produce generic versions of the drug, citing the interests of poor people who would not be able to afford Pfizer’s price.
Pfizer’s patent on sildenafil citrate expired in Brazil in 2010.
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Glimepiride is the generic name of the prescription drug Amaryl, used to treat patients with type 2 diabetes.
Glimepiride belongs to a class of drugs known as sulfonylureas.
It stimulates the pancreas to produce insulin and helps the body use insulin more efficiently.
The drug can also decrease the chances that someone will develop life-threatening complications of type 2 diabetes.
The drug was approved by the FDA in 1995 and is manufactured by Sanofi-Aventis.
Glimepiride comes in tablet form and is usually taken once a day.
It may be used alone, or in combination with insulin or another oral medication such as metformin.
Your doctor will probably start you on a low dose of the medication and gradually increase your dose if needed.
If you’ve taken glimepiride for a long period of time, the drug may not control blood sugar as well as it did when you first started the treatment.
Your doctor will adjust the dosage as needed.
Glimepiride Warnings Glimepiride helps control blood sugar, but it will not cure your diabetes.
You should continue to take glimepiride even if you feel well.
This medication should not be used to treat patients with type 1 diabetes, a disease in which the body does not produce insulin.
Glimepiride will only help lower blood sugar if your body produces insulin naturally.
In one study, patients who took a medication similar to glimepiride to treat diabetes were more likely to die of heart problems than those who were treated with diet changes and insulin.
Talk to your doctor about the risks of this treatment.
While taking glimepiride, you should tell your doctor if you: Are pregnant, plan to become pregnant, or are breastfeeding Are having surgery, including dental surgery Have ever had G6PD deficiency (a genetic blood disorder) Have hormone disorders involving the adrenal, pituitary, or thyroid gland Have heart, kidney, or liver disease BasicDescription Back to Top Glimepiride Side Effects Common Side Effects of Glimepiride Glimepiride may cause changes in your blood sugar, which could cause blood sugar levels to fluctuate.
Symptoms of low blood sugar include: Sudden sweating Shaking Fast heartbeat Hunger Blurred vision Dizziness Tingling in the hands or feet You may want to carry glucose tablets or gels with you to treat low blood sugar episodes.
Serious Side Effects of Glimepiride Some side effects of glimepiride can be serious.
You should call your doctor immediately if you experience: Yellowing of the skin or eyes ( jaundice ) Dark urine Light-colored stools Pain in the upper right part of the stomach Diarrhea Fever Sore throat Unusual bruising or bleeding Back to Top Glimepiride Interactions Many drugs can affect your blood sugar levels and make them more difficult to control.
You should talk with your doctor or pharmacist before you start, stop, or change any medication.
If you are taking another anti-diabetic drug such as chlorpropamide (Diabinese), follow your doctor’s instructions carefully for stopping the old drug and starting on glimepiride.
The drug colesevelam ( Welchol ) can decrease the absorption of glimepiride.
You will need to take glimepiride at least four hours before taking colesevelam.
You should tell your doctor about all prescription, non-prescription, illegal, recreational, herbal, nutritional, or dietary drugs or supplements you are taking.
Glimepiride and Alcohol Alcohol can worsen the side effects of glimepiride and may cause symptoms such as flushing, headache, chest pain, nausea, vomiting, weakness, blurred vision, mental confusion, sweating, choking, difficulty breathing, and anxiety.
Limit or avoid drinking alcohol while taking glimepiride.
You should also avoid unnecessary exposure to the sun while taking glimepiride because the drug can make your skin more sensitive to sunlight.
Back to Top Glimepiride Dosage You should take glimepiride as directed by your doctor.
Typically, you will take the medication by mouth with breakfast or with the first meal of the day, usually once daily.
Your dose will be based on your medical condition and response to treatment.
The recommended starting dose of glimepiride is 1 or 2 milligrams (mg), once a day with breakfast or first main meal.
If you are at increased risk for hypoglycemia (elderly patients or those with kidney impairment), you should start on 1 mg, once daily.
After reaching a daily dose of 2 mg, further dose increases can be made.
The maximum recommended dose is 8 mg, once daily.
Glimepiride Overdose If you suspect an overdose, you should contact a poison control center or emergency room immediately.
You can get in touch with a poison control center at (800) 222-1222.
Missed Dose of Glimepiride If you miss a dose of glimepiride, take it as soon as you remember.
If it’s almost time for the next dose, skip the missed dose and continue on your regular schedule.
Do not double up on doses to make up for a missed dose.
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Baclofen is a prescription drug used to treat muscle spasms from multiple sclerosis and Huntington’s disease as well as spinal cord injuries and spinal cord diseases.
Medical experts do not recommend baclofen for muscle spasms caused by rheumatoid arthritis, cerebral palsy, Parkinson’s disease, or stroke, because research to date does not support such use.
Baclofen is an antispastic muscle relaxant.
Researchers don’t know exactly how baclofen works; however, in general, it blocks nerve signals from muscles at the level of the spinal cord and it may also depress the central nervous system.
The Food and Drug Administration (FDA) approved baclofen in 1977 under the brand name Lioresal, which was made by Novartis.
The FDA approved generic baclofen in the 1980s.
Today, only generic versions of baclofen are available.
A case report published in Therapeutic Advances in Psychopharmacology in 2014 suggested that baclofen might be effective for treating marijuana dependence, particularly for those who have used the drug heavily for a long time.
The research also showed that baclofen may help reduce withdrawal symptoms as well as the effects of marijuana.
A separate study, published in the Journal of Neuroscience in 2014, found that baclofen may also help people with drug addiction avoid possible triggers and prevent relapse.
The drug works by interfering with the brain’s early response to drug cues.
Baclofen Pump You can take baclofen as a pill or via an intrathecal baclofen (ITB) pump.
In ITB therapy, your doctor will insert a small catheter under the skin of your abdomen, near your waist.
The pump stores and releases the prescribed amount of baclofen through the catheter, using a small motor, directly into your spinal fluid.
ITB can be an option for people who experience side effects taking baclofen in pill form as it requires smaller doses of the drug and thus keeps side effects to a minimum.
Your doctor will need to refill your ITB pump system every one to three months.
The system battery typically lasts five years, at which time your doctor will need to replace the device.
Baclofen Warnings Once you start taking baclofen, don’t stop taking it suddenly on your own.
If you need to stop, your doctor will lower your dose gradually.
Stopping baclofen suddenly can lead to a dangerous withdrawal reaction that can include hallucinations (seeing or hearing things that are not there) and seizures.
Your kidneys eliminate baclofen from your system.
Take baclofen with caution if you have kidney disease and reduced kidney function because the drug can build up in your system.
Baclofen is not recommended to treat muscle spasms caused by a stroke.
Baclofen can cause more side effects in people with a history of stroke.
Baclofen can make you drowsy and affect your balance, so don’t drive or operate heavy machinery until you know how baclofen affects you.
Other conditions you should tell your doctor about before taking baclofen include: Kidney disease Parkinson’s disease Stroke Seizures ( epilepsy ) Ulcers Cerebral palsy Mental health or mood disorders such as schizophrenia Rheumatoid arthritis The FDA has not approved baclofen for children younger than 12.
Baclofen and Pregnancy Studies have linked baclofen to birth defects in animals.
Because of this, it is considered unsafe to use during pregnancy.
Before taking this drug, tell your doctor if you are pregnant or may become pregnant.
Baclofen may pass into breast milk, so also tell your doctor if you are breastfeeding or plan to breastfeed.
If you’re a woman, ask your doctor about a possible risk for developing ovarian cysts while on baclofen.
Make sure you doctor knows if you have a history of ovarian cysts.
Baclofen “High” and Recreational Use Numerous online and anecdotal reports have suggested that some people abuse baclofen for a narcotic-like “high,” because it can cause drowsiness.
There is a high risk of overdose associated with recreational use of baclofen, as high doses are needed for narcotic-like effect.
Baclofen overdose can lead to: Coma Hypothhermia Dangerously slow heart rate/ bradycardia High blood pressure / hypertension Hyporeflexia (slower than normal reflexes) Take baclofen only as directed by your doctor, and keep this and all other drugs away from children, teenagers, and anyone for whom the drug has not been prescribed.
BasicDescription Back to Top Baclofen Side Effects The most common side effect experienced by people taking baclofen is drowsiness.
Other common side effects include: Dizziness Weakness Fatigue Less common side effects of baclofen include: Confusion Insomnia Headache Nausea Constipation Frequently passing urine Excitement Visual disturbance Loss of muscle coordination Dry mouth Loss of appetite Sexual impotence Serious side effects can also occur.
If you have any of these side effects, get emergency help or call 911: Chest pain Difficulty breathing Seizure Back to Top Baclofen Interactions Some drugs may affect the way baclofen works, and baclofen may affect other drugs you’re taking.
It’s very important to let your doctor know about all drugs you’re taking, including any other prescription drugs, over-the-counter drugs, recreational or illegal drugs, herbs, vitamins, or supplements.
Other drugs that depress the central nervous system may make some side effects of baclofen worse.
These drugs may include: Alcohol Sleeping pills Tranquilizers Muscle relaxants Vitamins Don’t drink alcohol while taking baclofen because that can worsen side effects such as drowsiness and dizziness.
Because baclofen relaxes muscles, it may cause weakness and imbalance, especially if you have muscle stiffness.
Talk to your doctor about how baclofen may affect your balance.
Back to Top Baclofen Dosage Baclofen comes in tablets of 10 and 20 milligrams (mg), and you’ll usually take an equally divided dose three times a day.
Tablets have a score mark, which is an indented line down the middle, so you can cut them in half if necessary.
Your doctor may start you at a low dose and then gradually increase it as needed.
The goal is to take the lowest effective dose.
A typical dose schedule is: 5 mg three times a day for the first three days; 10 mg three times a day for the next three days; 15 mg three times a day for the next three days; 20 mg three times a day for the next three days.
It may take a few weeks for the drug to reach the peak effectiveness.
The usual daily dose is 40 to 80 mg.
The maximum dose should not be higher than 80 mg a day.
Baclofen Overdose An overdose of baclofen can cause: Nausea Vomiting Severe muscle weakness Drowsiness Difficulty breathing Coma Seizure If you think you or someone else may have taken an overdose of baclofen, call your poison control center at 1-800-222-1222.
For severe symptoms of an overdose, call 911.
Baclofen Missed Dose Take baclofen exactly as directed by your doctor.
Don’t take more or less, and don’t stop taking baclofen on your own.
If you miss a dose, take it as soon as you remember.
But if it’s almost time for your next dose, skip the missed dose and continue your regular dose schedule.
Don’t double your dose to make up for the missed one.
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