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Mefenamic acid is a member of the anthranilic acid derivatives (or fenamate) class of NSAID drugs, and is used to treat mild to moderate pain, including menstrual pain, and is sometimes used to prevent migraines associated with menstruation. : 334
Its name derives from its systematic name, di me thyl phen yl am inobenzo ic acid. It was discovered and brought to market by Parke-Davis in the 1960s. It became generic in the 1980s and is available worldwide under many brand names.
Contents
1 Medical use
2 Side effects
3 Mechanism of action
4 History
5 Society and culture
5.1 Availability and pricing
5.2 Synthesis
6 Research
7 See also
8 References
9 Sources
Medical use
Mefenamic acid is used to treat moderate pain and menstrual pain.
There is evidence that supports the use of mefenamic acid for perimenstrual migraine headache prophylaxis, with treatment starting 2 days prior to the onset of flow or 1 day prior to the expected onset of the headache and continuing for the duration of menstruation.
Side effects
Mefenamic acid is recommended to be taken with food.
Known mild side effects of mefenamic acid include headaches, nervousness, and vomiting. Serious side effects may include diarrhea, hematemesis (vomiting blood), hematuria (blood in urine), blurred vision, skin rash, itching and swelling, sore throat and fever.
In 2008 the US label was updated with a warning concerning a risk of premature closure of the ductus arteriosus in pregnancy.
Mechanism of action
Like other members of the anthranilic acid derivatives (or fenamate) class of NSAID drugs, it inhibits both isoforms of COX and prevents formation of prostaglandins.
History
Scientists led by Claude Winder from Parke-Davis invented mefenamic acid in 1961, along with fellow members of the class of anthranilic acid derivatives, flufenamic acid in 1963 and meclofenamate sodium in 1964. : 918–919
It was approved in the UK in 1963 as “Ponstan”, in West Germany in 1964 as “Ponalar”, and in France as “Ponstyl” and the US in 1967 as “Ponstel”. : 918–919
Society and culture
Availability and pricing
Mefenamic acid is generic and is available worldwide under many brand names.
In the US, wholesale price of a week’s supply of generic mefenamic acid has been quoted as $426.90 in 2014. Brand-name Ponstel is $571.70. In the Philippines, 10 tablets of 500 mg generic mefenamic acid cost PHP39.00 (or the equivalent of US$0.88) as of October 25, 2014.
Synthesis
Analogous to fenamic acid, this compound may be made from 2-chlorobenzoic acid and 2,3-dimethylaniline.
Research
While studies have been conducted to see if mefenamic acid can improve behavior in transgenic mouse models of Alzheimer’s disease
See also
Niflumic acid

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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.
Contents
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
2.1 Interactions
2.2 Contraindications
3 Nonmedical use
3.1 Recreational use
3.2 Jet lag research
3.3 Sports
3.4 Analogs
4 Detection in biological fluids
5 Mechanism of action
6 Route of administration
7 Chemical synthesis
8 History
9 Society and culture
9.1 Marketing and sales
9.2 Counterfeits
9.3 Regional issues
9.3.1 European Union
9.3.2 United Kingdom
9.3.3 United States
9.3.4 Canada
9.3.5 India
9.3.6 China
9.3.7 New Zealand
9.3.8 Other countries
10 References
11 External links
Medical uses
Pfizer Viagra tablet in the trademark blue diamond shape
Sexual dysfunction
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.
Pulmonary hypertension
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
Raynaud’s phenomenon
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.
Adverse effects
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.
Interactions
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
Contraindications include: : 11
Concomitant use of nitric oxide donors, organic nitrites and nitrates, such as:
nitroglycerin
isosorbide mononitrate
isosorbide dinitrate
sodium nitroprusside
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
Nonmedical use
Recreational use
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.
Sports
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.
Analogs
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.
Chemical synthesis
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
Cyclization
Sulfonation to the chlorosulfonyl derivative
Condensation with 1-methylpiperazine.
History
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.
Counterfeits
Further information: Counterfeit medications
Counterfeit Viagra, despite generally being cheaper,
Viagra is one of the world’s most counterfeited medicines.
Regional issues
European Union
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.
United Kingdom
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.
United States
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.
Canada
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.
India
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 ).
China
Manufacture and sale of sildenafil citrate drugs is common in China, where Pfizer’s patent claim is not widely enforced.
New Zealand
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.
Other countries
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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Ipratropium bromide was developed in Germany in 1976.
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It is also combined with salbutamol ( albuterol — USAN ) under the trade names Combivent (a non-aerosol metered-dose inhaler or MDI) and Duoneb ( nebulizer ) for the management of COPD and asthma, and with fenoterol (trade names Duovent and Berodual N) for the management of asthma.
Ipratropium as a nasal solution sprayed into the nostrils can reduce rhinorrhea but will not help nasal congestion.
Combination with beta-adrenergic agonists increases the dilating effect on the bronchi.
Contraindications
The main contraindication for inhaled ipratropium is hypersensitivity to atropine and related substances. For oral administration, contraindications are similar to other anticholinergics; they include narrow angle glaucoma and obstructions in the gastrointestinal tract and urinary system.
Peanut allergy
Previously atrovent inhalers used chlorofluorocarbon (CFC) as a propellant and contained soy lecithin in the propellant ingredients. In 2008 all CFC inhalers were phased out and hydrofluoroalkane (HFA) inhalers replaced them. Allergy to peanuts was noted for the inhaler as a contraindication but now is not. It has never been a contraindication when administered as a nebulized solution.
Side effects
If ipratropium is inhaled, side effects resembling those of other anticholinergics are minimal. However, dry mouth and sedation have been reported. Also, effects such as skin flushing, tachycardia, acute angle-closure glaucoma, nausea, palpitations and headache have been observed. Inhaled ipratropium does not decrease mucociliary clearance.
Urinary retention has been reported in patients receiving doses by nebulizer. As a result, caution may be warranted, especially by men with prostatic hypertrophy.
Interactions
Interactions with other anticholinergics like tricyclic antidepressants, anti-Parkinson drugs and quinidine, which theoretically increase side effects, are clinically irrelevant when ipratropium is administered as an inhalant.
Pharmacology
Chemically, ipratropium bromide is a quaternary ammonium compound (which is indicated by the -ium per the BAN and the USAN )
Ipratropium exhibits broncholytic action by reducing cholinergic influence on the bronchial musculature. It blocks muscarinic acetylcholine receptors, without specificity for subtypes, and therefore promotes the degradation of cyclic guanosine monophosphate (cGMP), resulting in a decreased intracellular concentration of cGMP. but is a quaternary amine and therefore does not cross the blood–brain barrier, which prevents central side effects (anticholinergic syndrome). Ipratropium should never be used in place of salbutamol (albuterol) as a rescue medication.

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Diltiazem ( INN ) ( / d ɪ l ˈ t aɪ ə z ɛ m / ) is a nondihydropyridine (non-DHP) calcium channel blocker used in the treatment of hypertension, angina pectoris, and some types of arrhythmia. It relaxes the smooth muscles in the walls of arteries, which opens (dilates) the arteries, allows blood to flow more easily, and lowers blood pressure. Additionally, it lowers blood pressure by acting on the heart itself to reduce the rate, strength, and conduction speed of each beat.
It is also used off-label as a preventive medication for migraine. It is a Class 3 antianginal drug, and a Class IV antiarrhythmic.
Diltiazem is metabolized by, and acts as an inhibitor of the CYP3A4 enzyme, which can cause it to interact with a variety of other medications.
Contents
1 Mechanism
2 Nontherapeutic effects and toxicities
3 Indications
4 Contraindications and precautions
5 Drug interactions
5.1 Beta-blockers
5.2 Quinidine
6 Potential future indications
7 References
8 External links
Mechanism
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Diltiazem is a potent vasodilator, increasing blood flow and variably decreasing the heart rate via strong depression of A-V node conduction. Its pharmacological activity is somewhat similar to verapamil, another nondihydropyridine (non-DHP) calcium channel blocker. Chemically, it is based upon a 1,4-thiazepine ring, making it a benzothiazepine -type calcium channel blocker.
It is a vasodilator of coronary and peripheral vessels, which reduces peripheral resistance and afterload, though not as potent as the dihydropyridine (DHP) calcium channel blockers. This results in minimal reflexive sympathetic changes.
Diltiazem has negative inotropic, chronotropic, and dromotropic effects. This means diltiazem causes a decrease in heart muscle contractility – how strong the beat is, lowering of heart rate – due to slowing of the sinoatrial node, and a slowing of conduction through the atrioventricular node – increasing the time needed for each beat. Each of these effects results in reduced oxygen consumption by the heart, reducing angina symptoms. These effects also reduce blood pressure by causing less blood to be pumped out.
Nontherapeutic effects and toxicities
A reflex sympathetic response, caused by the peripheral dilation of vessels and the resulting drop in blood pressure, works to counteract the negative inotropic, chronotropic and dromotropic effects of diltiazem. Undesirable effects include hypotension, bradycardia, dizziness, and flushing.
Indications
Diltiazem is indicated for:
Stable angina (exercise-induced) – diltiazem increases coronary blood flow and decreases myocardial oxygen consumption, secondary to decreased peripheral resistance, heart rate, and contractility.
Variant angina – it is effective owing to its direct effects on coronary dilation.
Unstable angina ( preinfarction, crescendo ) – diltiazem may be particularly effective if the underlying mechanism is vasospasm.
Myocardial bridge
For supraventricular tachycardias ( PSVT ), diltiazem appears to be as effective as verapamil in treating re-entrant supraventricular tachycardia.
Atrial fibrillation or atrial flutter is another indication. The initial bolus should be 0.25 mg/kg, intravenous (IV).
Because of its vasodilatory effects, diltiazem is useful for treating hypertension. Calcium channel blockers are well tolerated, and especially effective in treating low- renin hypertension.
Contraindications and precautions
In congestive heart failure, patients with reduced ventricular function may not be able to counteract the inotropic and chronotropic effects of diltiazem, the result being an even higher compromise of function.
With SA node or AV conduction disturbances, the use of diltiazem should be avoided in patients with SA or AV nodal abnormalities, because of its negative chronotropic and dromotropic effects.
Low blood pressure patients, with systolic blood pressures below 90 mm Hg, should not be treated with diltiazem.
Diltiazem may paradoxically increase ventricular rate in patients with Wolff-Parkinson-White syndrome because of accessory conduction pathways.
Diltiazem is relatively contraindicated in the presence of sick sinus syndrome, atrioventricular node conduction disturbances, bradycardia, impaired left ventricle function, peripheral artery occlusive disease, and chronic obstructive pulmonary disease.
Drug interactions
Because of its inhibition of hepatic cytochromes CYP3A4, CYP2C9 and CYP2D6, there are a significant number of drug interactions. Some of the more important interactions are listed below.
Beta-blockers
Intravenous diltiazem should be used with caution with beta-blockers because, while the combination is most potent at reducing heart rate, there are rare instances of dysrhythmia and AV node block.
Quinidine
Quinidine should not be used concurrently with calcium channel blockers because of reduced clearance of both drugs and potential pharmacodynamic effects at the SA and AV nodes.
Potential future indications
Diltiazem is prescribed off-label by doctors in the US for prophylaxis of cluster headaches. Some research on diltiazem and other calcium channel antagonists in the treatment and prophylaxis of migraine is ongoing.
Recent research
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Lisinopril was the third ACE inhibitor (after captopril and enalapril ) and was introduced into therapy in the early 1990s. A number of properties distinguish it from other ACE inhibitors: It is hydrophilic, has a long half-life and tissue penetration, and is not metabolized by the liver.
Contents
1 Medical uses
1.1 Specific populations
1.1.1 Kidney problems
1.1.2 Pregnancy and breastfeeding
2 Contraindications
3 Adverse effects
4 Overdose
5 Interactions
5.1 Dental care
6 Pharmacology
6.1 Mechanism of action
6.2 Pharmacokinetics
6.2.1 Absorption
6.2.2 Distribution
6.2.3 Metabolism
6.2.4 Elimination
7 Chemistry
8 History
9 References
10 Further reading
11 External links
Medical uses
Lisinopril is typically used for the treatment of high blood pressure, congestive heart failure, acute myocardial infarction (heart attack), and diabetic nephropathy.
A systematic review concluded that lisinopril was highly effective for treatment of proteinuric kidney disease, including diabetic proteinuria.
Specific populations
Caution should be used in the following populations, as dose adjustments may be required.
Kidney problems
The dose must be adjusted in those with poor kidney function. Dose adjustments may be required when creatinine clearance is less than or equal to 30mL/min. Since lisinopril is removed by dialysis, dosing changes must also be considered for people on dialysis.
Pregnancy and breastfeeding
Lisinopril has been assigned to pregnancy category D by the FDA. Animal and human data have revealed evidence of lethal harm to the embryo and teratogenicity associated with ACE inhibitors. No controlled data in human pregnancy are available. Birth defects have been associated with use of lisinopril in any trimester. However, there have been reports of death and increased toxicities to the fetus and newly born child with the use of lisinopril in the second and third trimesters. The label states, “When pregnancy is detected, discontinue Zestril as soon as possible.” The manufacturer recommends mothers should not breastfeed while taking this medication because of the lack of safety data that currently exists.
Contraindications
Treatment with lisinopril should be avoided for people who have a history of angioedema ( hereditary or idiopathic ) or who have diabetes and are taking aliskiren.
Adverse effects
The incidence of adverse effects varies according to which disease state the patient is being treated for.
People taking lisinopril for the treatment of hypertension may experience the following side effects:
Headache (3.8%)
Dizziness (3.5%)
Cough (2.5%)
Difficulty swallowing or breathing (signs of angioedema ), allergic reaction ( anaphylaxis )
Hyperkalemia (2.2% in adult clinical trials)
Fatigue (1% or more)
Diarrhea (1% or more)
Some severe skin reactions have been reported rarely, including toxic epidermal necrolysis and Stevens-Johnson syndrome ; causal relationship has not been established.
People taking lisinopril for the treatment of myocardial infarction may experience the following side effects:
Hypotension (5.3%)
Renal dysfunction (1.3%)
People taking lisinopril for the treatment of heart failure may experience the following side effects:
Hypotension (3.8%)
Dizziness (12% at low dose – 19% at high dose)
Chest pain (2.1%)
Fainting (5-7%)
Hyperkalemia (3.5% at low dose – 6.4% at high dose)
Difficulty swallowing or breathing (signs of angioedema ), allergic reaction ( anaphylaxis )
Fatigue (1% or more)
Diarrhea (1% or more)
Some severe skin reactions have been reported rarely, including toxic epidermal necrolysis and Stevens-Johnson syndrome ; causal relationship has not been established.
Lisinopril 40-mg oral tablet
Overdose
In one reported overdose, the half-life of lisinopril was prolonged to 14.9 hours.
Interactions
Dental care
ACE-inhibitors like lisinopril are considered to be generally safe for people undergoing routine dental care, though the use of lisinopril prior to dental surgery is more controversial, with some dentists recommending discontinuation the morning of the procedure.
Pharmacology
Lisinopril is the lysine -analog of enalapril. Unlike other ACE inhibitors, it is not a prodrug and is excreted unchanged in the urine.
Mechanism of action
Lisinopril is an ACE inhibitor, meaning it blocks the actions of angiotensin-converting enzyme (ACE) in the renin-angiotensin-aldosterone system (RAAS), keeping angiotensin I from being converted to angiotensin II. This prevents the release of aldosterone from the adrenal cortex, which allows the kidney to excrete sodium along with water into the urine, and retention of potassium ions.
Pharmacokinetics
Absorption
Lisinopril has a poor bioavailability of 25% (reduced to 16% in people with NYHA Class II-IV heart failure).
Distribution
Lisinopril does not bind to proteins in the blood.
Metabolism
Lisinopril is the only water-soluble member of the ACE inhibitor class, with no hepatic metabolism.
Elimination
Lisinopril leaves the body completely unchanged in the urine.
Chemistry
Pure lisinopril powder is white to off-white in color.
History
Captopril, the first ACE inhibitor, is a functional and structural analog of a peptide derived from the venom of the jararaca, a Brazilian pit viper ( Bothrops jararaca ). : 12–13
Enalapril is actually a prodrug ; the active metabolite is enalaprilat.
Lisinopril is a synthetic peptide derivative of captopril.
The discovery posed a problem, since sales of enalapril were strong for Merck, and the company did not want to diminish those sales. Merck ended up entering into an agreement with Zeneca under which Zeneca received the right to co-market lisinopril, and Merck received the exclusive rights to an earlier stage aldose reductase inhibitor drug candidate, a potential treatment for diabetes. Zeneca’s marketing and brand name, “Zestril”, turned out to be stronger than Merck’s effort.
The US patents expired in 2002.

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Albendazole, also known as albendazolum,
Common side effects include nausea, abdominal pains, and headaches.
Albendazole was developed in 1975.
Contents
1 Medical uses
1.1 Pregnancy
2 Contraindications
3 Side effects
4 Overdose
5 Interactions
6 Pharmacology
6.1 Mechanism of action
6.2 Pharmacokinetics
7 History
8 Society and culture
8.1 Brand names
8.2 Cost
9 Veterinary use
9.1 Meat
10 See also
11 References
12 External links
Medical uses
Albendazole is an effective treatment for:
Flatworms
Fasciolosis
Cestodes (tapeworms), as an alternative to praziquantel or niclosamide for adult beef tapeworms ( Taenia saginata ) and as an alternative to praziquantel for pork tapeworms ( T. solium ).
Cysticercosis
Hydatic disease (aka echinococcosis)
Nematodes
Ascariasis, which can be cured with a single dose of albendazole.
Baylisascariasis, caused by the raccoon roundworm. Corticosteroids are sometimes added in cases of eye and CNS infections.
Enterobiasis ( pinworm infection)
Filariasis ; since albendazole’s disintegration of the microfilarie (“pre-larva”) can cause an allergic reaction, antihistamines or corticosteroids are sometimes added to treatment. In cases of lymphatic filariasis (elephantiasis) caused by Wuchereria bancrofti or Brugia malayi, albendazole is sometimes given as an adjunct to ivermectin or diethylcarbamazine in order to suppress microfilaremia. It can also be given for loa loa filariasis as an adjunct or replacement to diethylcarbamazine.
Gnathostomiasis when caused by Gnathostoma spinigerum.
Gongylonemiasis
Hookworm infections,
Intestinal capillariasis,
Mansonelliasis when caused by Mansonella perstans. Albendazole works against the adult worms but not against the younger microfilariae.
Oesophagostomumiasis, when caused by Oesophagostomum bifurcum
Strongyloidiasis,
Toxocariasis, also called “visceral larva migrans”, when caused by the dog roundworm Toxocara canis or cat roundworm T. catis. Corticosteroids can be added in severe cases, and surgery might be required to repair secondary damage.
Trichinosis, when caused by Trichinella spiralis
Trichostrongyliasis, as an alternative to pyrantel pamoate.
Trichuriasis (whipworm infection),
Giardiasis, as an alternative or adjunct to metronidazole, especially in children
Microsporidiosis, including ocular microsporidiosis caused by Encephalitozoon hellem or E. cuniculi, when combined with topical fumagillin
Granulomatous amoebic encephalitis, when caused by the ameba Balamuthia mandrillaris, in combination with miltefosine and fluconazole
Arthropods
Crusted scabies, when combined with topical crotamiton and salicylic acid
Head lice infestation, though ivermectin is much better
Intestinal myiasis
Though albendazole is effective in treating many diseases, it is only FDA-approved for treating hydatid disease caused by dog tapeworm larvae and neurocysticercosis caused by pork tapeworm larvae.
Pregnancy
Albendazole is a pregnancy class D drug in Australia and pregnancy class C in the United States. It is contraindicated in the first trimester of pregnancy, and should be avoided up to one month before conception. While studies in pregnant rats and rabbits have shown albendazole to be teratogenic,
In pregnant dogs, albendazole use has led to puppies with reduced weight and with cleft palates. Birds have lower rates of laying eggs and hatching when given albendazole.
Albendazole sulfoxide is secreted into breast milk at around 1.5% of the maternal dose, though oral absorption is poor enough that it is unlikely to affect nursing infants.
Contraindications
Hypersensitivity to the benzimidazole class of compounds contraindicates its use.
Side effects
Close-up of a pork tapeworm cyst. Destruction of these cysts can cause inflammation.
The most common side effects by albendazole are, experienced by over 10% of people, headache and abnormal liver function.
Side effects can be different when treating for hydatid disease versus neurocysticercosis; for example, those being treated for the former are more likely to experience elevated liver enzymes and abdominal pain; those being treated for the latter are more likely to experience headache.
Overdose
Because of its low solubility, albendazole often cannot be absorbed in high enough quantities to be toxic.
Interactions
The antiepileptics carbamazepine, phenytoin, and phenobarbital lower the plasma concentration and the half life of albendazole sulfoxide’s R(+) enantiomer.
Antiepileptics and pharmacokinetics of albendazole sulfoxide
Drug
Change in AUC
Change in C max
Carbamazepine
49% decrease
50–63% decrease
Phenobarbitol
61% decrease
50–63% decrease
Phenytoin
66% decrease
50–63% decrease
The antacid cimetidine heightens serum albendazole concentrations, increases the half life of albendazole, and doubles albendazole sulfoxide levels in bile.
Several other interactions exist. Corticosteroids increase the steady-state plasma concentration of albendazole sulfoxide;
Pharmacology
A microtubule is composed of polymers of α- and β-tubulin.
Mechanism of action
As a vermicide, albendazole causes degenerative alterations in the intestinal cells of the worm by binding to the colchicine -sensitive site of β-tubulin, thus inhibiting its polymerization or assembly into microtubules (it binds much better to the β-tubulin of parasites than that of mammals). Due to diminished ATP production, the parasite is immobilized and eventually dies.
Some parasites have evolved to have some resistance to albendazole by having a different set of acids comprising β-tubulin, decreasing the binding affinity of albendazole.
Pharmacokinetics
Oral absorption of albendazole varies among species, with 1–5% of the drug being successfully absorbed in humans, 20–30% in rats, and 50% in cattle.
The absorption also largely depends on gastric pH. People have varying gastric pHs on empty stomachs, and thus absorption from one person to another can vary wildly when taken without food.
Absorption is also affected by how much of the albendazole is degraded within the small intestine by metabolic enzymes in the vili.
General metabolism of albendazole and its sulfoxides.
The pharmacokinetics of albendazole differ slightly between men and women: women have a lower oral clearance and volume of distribution, while men have a lower serum peak concentration.
Albendazole undergoes very fast 1st-pass metabolism in all species, such that the unchanged drug is undetectable in plasma.
While oxidation to albendazole sulfoxide by FMO produces R(+) enantiomers, while oxidation the cytochromes and by some enzymes in the gut epithelium produce S(-). Different species produce the R(+) and S(-) enantiomers in different quantities; humans, dogs, and most other species
For systemic parasites, albendazole acts as a prodrug, while albendazole sulfoxide reaches systemic circulation and acts as the real antihelminthic.
Albendazole sulfoxide is converted to the inactive albendazole sulfone by cytochrome P450 oxidases, thought to include CYP3A4
methyl carbamate,
methyl carbamate,
methyl carbamate,
5-(n-propylsulfonyl)-1H-benzimidazole-2-yl amine, and
5-(n-propysulfinyl)-1H-benzimidazole-2-yl amine.
There are also some minor hydroxylated sulfated or glucuronidated derivatives.
In humans, the metabolites mostly excreted in the bile, with only a small amount being excreted in the urine (less than 1%) and feces.
Like all benzimidazoles, albendazole has no residual effect, and thus does not protect well against reinfestations.
History
Albendazole, patented in 1975, was invented by Robert J. Gyurik and Vassilios J. Theodorides and assigned to SmithKline Corporation.
Society and culture
Discarded bottles of albendazole distributed in Africa
Brand names
Brand names include: Albenza, Alworm, Andazol, Eskazole, Noworm, Zentel, Alben-G, ABZ, Cidazole, Wormnil etc.
Cost
In many areas of the world it costs between US$0.01 and US$0.06 per dose.
In Raleigh, North Carolina, the brand-name prescription cost was around US$800, and US$540 for the generic. The pharmaceutical company Amedra increased the price after purchasing the rights to the drug, instead of lowering it as generics are predicted to do, drawing criticism from patients’ rights advocates and US Democratic Party leaders.
In 2013, GlaxoSmithKline donated 763 million albendazole tablets for the treatment and prevention of parasitic infections in developing countries, bringing the total to over 4 billion tablets donated since 1998.
Veterinary use
Albendazole is mainly used in cattle and sheep, but has found some use in cats and dogs as well;
Albendazole use in animals
Cattle
Sheep
Others
Platyhelminthes (flatworms)
Trematodes
Dicrocoelium (liver flukes)
D. dendriticum (lancet liver fluke)
D. dendriticum
Fasciola (liver flukes)
F. hepatica
F. hepatica
For F. hepatica and F. gigantica in people
Fascioloides (liver flukes)
F. magna
F. magna
Also for F. magna in South American camelids (ex. llama and alpaca)
Paragonimus (lung flukes)


For P. kellicotti in cats and dogs
Platynosomum


For Platynosomum infections in cats
Opisthorchiidae


For Opisthorchiidae infections in cats
Cestodes (tapeworms)
Echinococcus


For Echinococcus cysts in horses and humans
Moniezia
M. expansa M. benedini
M. expansa  
Taenia
T. saginata larvae

For T. saginata, T. solium, and T. crassiceps in humans
Thysanosoma

T. actinoides
Nematodes (roundworms)
Ancylostoma


For Ancylostoma infections in dogs, cats, and humans
Bunostomum
B. phlebotomum

Capillaria


For causative agents of various forms of capillariasis in cats and dogs (including C. philippinensis, C. hepatica, C. aerophila, and C. plica ) and intestinal capillariasis ( C. philippinensis ) in humans.
Chabertia

C. ovina
Cooperia
C. oncophora C. punctata
C. oncophora  
Dictyocaulus (lungworm)
D. viviparus
D. filaria
For D. amfieldi infections in horses
Filaroides (lungworm)


For F. hirthi and F. osleri in dogs
Haemonchus
H. contortus H. placei
H. contortus  
Marshallagia

M. marshalli
Metastrongylus


For M. apri in swine
Nematodirus
N. spathiger N. helvetianus
N. spathiger N. filicollis
Parascaris


For P. equorum in horses
Ostertagia
O. ostertagi
O. circumcincta
For O. bifurcum in humans
Oesophagostomum
O. radiatum
O. columbianum
Strongyloides


For S. stercoralis in dogs and humans
Strongylus


For S. equinus in horses
Toxocara


For T. canis infections in dogs and toxocariasis in humans (caused by T. canis and T. cati )
Trichostrongylus
T. axei T. colubriformis
T. axei T. colubriformis
For any Trichostrongylus infection in humans
Trichuris (whipworm)
Most species, but those usually found in cattle are: T. discolor T. globulosa T. ovis
Most species, but those usually found in sheep are: T. discolor T. globulosa T. ovis
Albendazole is also used for Trichuris infections in humans (usually T. trichiura, causative agent of trichuriasis), dogs (usually T. vulpis and T. campanula ), cats (usually T. serrata and T. campanula ), pigs (usually T. suis ), and other ruminants (same species as those found in cattle and sheep).
Other
Encephalitozoon


For E. cuniculi infections (microsporidiosis) in humans and rabbits
Giardia
G. lamblia (causative agent of giardiasis )

Also treats giardiasis in humans, dogs, and small mammals
Leishmania


Treats leishmaniasis, caused by various species of Leishmania, in dogs
Albendazole has been used as an anthelminthic and for control of flukes in a variety of animal species, including cattle, sheep, goats, swine, camels, dogs, cats, elephants, poultry, and others.
It is extensively used for ruminant livestock in Latin America.
Albendazole has greater bioavailability in ruminants: some albendazole sulfoxide, when released back into the rumen, is reduced to albendazole by the resident microbiota, with a preference of the (+) enantiomer being the substrate.
Meat
This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (August 2017) ( Learn how and when to remove this template message )
The limitations in early pregnancy are due to a limited period during which teratogenic effects may occur. Summarized research data relating to the durations of these preslaughter and early pregnancy periods when albendazole should not be administered are found in US FDA NADA 110-048 (cattle) and 140-934 (sheep). Some data and inferences regarding goats are found in US FDA Supplemental NADA 110-048 (approved January 24, 2008).
Maximum residue limits (MRLs) for albendazole in food, adopted by the FAO/WHO Codex Alimentarius in 1993, are 5000, 5000, 100, and 100 micrograms per kilogram of body weight (μg/kg) for kidney, liver, fat, and muscle, respectively, and 100 μg/L for milk. For analysis purposes, MRLs of various nations may pertain to concentration of a marker substance which has been correlated with concentrations of the administered substance and its metabolized products. For example, in Canada, the marker substance specified by Health Canada is albendazole-2-aminosulfone, for which the MRL in liver of cattle is 200 μg/kg.
There is a 27 days cattle withdrawal time for meat.
See also
Mebendazole
Eradication of infectious disease
Neglected tropical diseases

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Calcitriol ( INN ), also called 1,25-dihydroxycholecalciferol, or 1alpha,25-dihydroxyvitamin D3, 1,25-dihydroxyvitamin D 3 and other variants, is the hormonally active metabolite of vitamin D which has three hydroxyl groups. It can be abbreviated 1α,25-(OH) 2 D 3 or simply 1,25(OH) 2 D.
Contents
1 Nomenclature
2 Function
3 Biosynthesis and its regulation
4 Metabolism
5 Medical use
6 Adverse effects
7 History
8 Interactive pathway map
9 Additional images
10 See also
11 References
Nomenclature
Calcitriol usually refers specifically to 1,25-dihydroxycholecalciferol. Because cholecalciferol already has one hydroxyl group, only two (1,25) are further specified in this nomenclature, but there are three (1,3,25-triol), as indicated in when calcitriol is used. The 1-hydroxy group is in the alpha position, and this may be specified in the name, for instance in the abbreviation 1α,25-(OH) 2 D 3.
Calcitriol is the strictly the 1-hydroxylation product of calcifediol (25-OH vitamin D 3 ), derived from cholecalciferol (vitamin D 3 ), rather than the product of hydroxylations of ergocalciferol (vitamin D 2 ).
Calcitriol is marketed as a pharmaceutical for medical use under various trade names including Rocaltrol ( Roche ), Calcijex ( Abbott ), Decostriol (Mibe, Jesalis), Vectical ( Galderma ), and Rolsical ( Sun Pharma ).
Function
Calcitriol increases blood calcium levels ([ Ca 2+ ]) by:
Promoting absorption of dietary calcium from the gastrointestinal tract.
Increasing renal tubular reabsorption of calcium, thus reducing the loss of calcium in the urine.
Stimulating release of calcium from bone. For this it acts on the specific type of bone cells referred to as osteoblasts, causing them to release RANKL, which in turn activates osteoclasts.
Calcitriol acts in concert with parathyroid hormone (PTH) in all three of these roles. For instance, PTH also indirectly stimulates osteoclasts. However, the main effect of PTH is to increase the rate at which the kidneys excrete inorganic phosphate (P i ), the counterion of Ca 2+. The resulting decrease in serum phosphate causes hydroxyapatite (Ca 5 (PO 4 ) 3 OH) to dissolve out of bone thus increasing serum calcium. PTH also stimulates the production of calcitriol (see below).
Many of the effects of calcitriol are mediated by its interaction with the calcitriol receptor, also called the vitamin D receptor or VDR. For instance, the unbound inactive form of the calcitriol receptor in intestinal epithelial cells resides in the cytoplasm. When calcitriol binds to the receptor, the ligand -receptor complex translocates to the cell nucleus, where it acts as a transcription factor promoting the expression of a gene encoding a calcium binding protein. The levels of the calcium binding protein increase enabling the cells to actively transport more calcium ( Ca 2+ ) from the intestine across the intestinal mucosa into the blood.
The maintenance of electroneutrality requires that the transport of Ca 2+ ions catalyzed by the intestinal epithelial cells be accompanied by counterions, primarily inorganic phosphate. Thus calcitriol also stimulates the intestinal absorption of phosphate.
The observation that calcitriol stimulates the release of calcium from bone seems contradictory, given that sufficient levels of serum calcitriol generally prevent overall loss of calcium from bone. It is believed that the increased levels of serum calcium resulting from calcitriol-stimulated intestinal uptake causes bone to take up more calcium than it loses by hormonal stimulation of osteoclasts. Only when there are conditions, such as dietary calcium deficiency or defects in intestinal transport, which result in a reduction of serum calcium does an overall loss of calcium from bone occur.
Calcitriol also inhibits the release of calcitonin,
Biosynthesis and its regulation
Calcitriol is produced in the cells of the proximal tubule of the nephron in the kidneys by the action of 25-hydroxyvitamin D 3 1-alpha-hydroxylase, a mitochondrial oxygenase and an enzyme which catalyzes the hydroxylation of 25-hydroxycholecalciferol (calcifediol) in the 1-alpha position.
The activity of this enzyme is stimulated by PTH. This is an important control point in Ca 2+ homeostasis.
Calcitriol is also produced outside the kidney in small amounts by many other tissues including placenta and activated macrophages.
When the drug alfacalcidol is used, 25-hydroxylation in the liver will produce calcitriol as the active metabolite. This will produce greater effects than other vitamin D precursors in patients with kidney disease who have loss of the renal 1-alpha-hydroxylase.
Metabolism
Calcitriol’s lifespan in the body is measured in hours, unlike its precursor calcifediol whose lifespan is measured in weeks. Calcitroic acid is more soluble in water and is excreted in bile and urine.
Medical use
Calcitriol is prescribed for:
Treatment of hypocalcaemia – hypoparathyroidism, osteomalacia (adults), rickets (infants, children), renal osteodystrophy, chronic kidney disease
Treatment of osteoporosis
Prevention of corticosteroid-induced osteoporosis
Calcitriol has been used in an ointment for the treatment of psoriasis,
Adverse effects
The main adverse drug reaction associated with calcitriol therapy is hypercalcemia – early symptoms include: nausea, vomiting, constipation, anorexia, apathy, headache, thirst, pruritus, sweating, and/or polyuria. Compared to other vitamin D compounds in clinical use ( cholecalciferol, ergocalciferol ), calcitriol has a higher risk of inducing hypercalcemia. However, such episodes may be shorter and easier to treat due to its relatively short half-life.
History
It was first identified in 1971 by Michael F. Holick working in the laboratory of Hector DeLuca,
Interactive pathway map
Click on genes, proteins and metabolites below to link to respective articles.
[[File:
|{{{bSize}}}px|alt=Vitamin D Synthesis Pathway ( view / edit )]]
Vitamin D Synthesis Pathway ( view / edit )
^ The interactive pathway map can be edited at WikiPathways: “VitaminDSynthesis_WP1531”.
Additional images
Calcitriol synthesis
See also
Vitamin D
Calcium metabolism
Calcitroic acid

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Drospirenone, sold under the brand names Yasmin and Angeliq among others, is a progestin medication which is used in birth control pills to prevent pregnancy and in menopausal hormone therapy, among other uses.
Rare side effects of drospirenone may include high potassium levels and blood clots, among others. Drospirenone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.
Drospirenone was introduced for medical use in 2000.
Contents
1 Medical uses
1.1 Available forms
1.1.1 Formulations
2 Contraindications
3 Side effects
3.1 High potassium levels
3.2 Blood clots
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.1.1 Progestogenic activity
6.1.2 Antimineralocorticoid activity
6.1.3 Antiandrogenic activity
6.2 Pharmacokinetics
7 Chemistry
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Availability
9.4 Litigation
10 Research
11 References
12 Further reading
13 External links
Medical uses
Drospirenone is an ingredient in some birth control pills and is used in menopausal hormone therapy. In combination with ethinylestradiol it is used as contraception, and for women who want contraception it is also approved by the U.S. Food and Drug Administration (FDA) to treat moderate acne and premenstrual dysphoric disorder.
Angeliq, a drospirenone and estradiol combination, has also been approved by the Food and Drug Administration (FDA) for treatment of moderate to severe vasomotor symptoms and/or vaginal atrophy associated with menopause.
The FDA has several approved indications for combined estrogen and drospirenone preparations. They are approved as a first-line therapy for menopausal symptoms such as the relief of hot flashes.
Available forms
Drospirenone is sold as a combined birth control pill under the brand names Yasmin (US, EU, Latin America), Jasmine (France), Yarina (Russia)
Formulations
See also: Oral contraceptive formulations
Drospirenone is a component of oral contraceptive formulations including the following:
Yasmin/Jamine/Yarina contains 3 mg drospirenone and 30 µg ethinylestradiol per tablet. It is indicated for the prevention of pregnancy in women who elect an oral contraceptive.
Safyral contains 3 mg drospirenone and 30 µg ethinylestradiol per tablet. It is indicated for the prevention of pregnancy in women who elect an oral contraceptive as well as to provide a daily dose of folate supplementation, which is recommended for women in their reproductive years. Folate lowers the risk of having rare neural tube birth defects in a pregnancy occurring during Safyral use or shortly after stopping.
Yaz/Gianvi/Vestura contains 3 mg drospirenone and 20 µg ethinylestradiol per tablet. It is indicated for prevention of pregnancy as well as treatment of premenstrual dysphoric disorder for women who choose to use an oral contraceptive for contraception. There has also been evidence for this formulation to treat moderate acne for women 14 years of age or older who choose to use an oral contraceptive for birth control.
A complete list of FDA approved oral contraceptives containing drospirenone as of October 2012: Beyaz (Drospirenone 3 mg, ethinylestradiol 0.02 mg and levomefolate calcium 0.451 mg), Drospirenone and ethinylestradiol (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Gianvi (Drospirenone 3 mg and ethinylestradiol 0.02 mg), Loryna (Drospirenone 3 mg and ethinylestradiol 0.02 mg), Ocella (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Safyral (Drospirenone 3 mg, ethinylestradiol 0.03 mg, and levomefolate calcium 0.451 mg), Syeda (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Yasmin (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Zarah (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Yaz (Drospirenone 3 mg and ethinylestradiol 0.02 mg)
Contraindications
See also: Progestin § Contraindications
In addition to contraindications common to all combined estrogen–progestin medications, drospirenone-containing medications are contraindicated in women with severe renal insufficiency according to European Medicines Agency (EMA)-approved labels,
Side effects
High potassium levels
Drospirenone is an antimineralocorticoid with potassium -sparing properties, though in most cases no increase of potassium levels is to be expected.
Blood clots
While all oral contraceptives can increase the risk for venous thrombembolic events, including fatal blood clots, several studies have reported a greater risk for women taking contraceptives containing drospirenone. Women who take contraceptive pills containing drospirenone have a 6- to 7-fold risk of developing thromboembolism (dangerous blood clots) compared to women who do not take any contraceptive pill, and have twice the risk (some epidemiological studies suggest thrice, according to the FDA) compared to women who take a contraceptive pill containing levonorgestrel. However, the absolute risk is small, in the neighborhood of 9 to 27 out of 10,000 women on an oral contraceptive for a year (up to 9 for levonorgestrel vs up to 27 for drospirenone, or about 0.09% vs 0.3% per year).
When the U.S. Food and Drug Administration (FDA) became concerned about the risks of drospirenone, they funded studies based on the medical records of more than 800,000 women taking oral contraceptives. They found that the risk of VTE, which includes dangerous and potentially fatal blood clots, was 93% higher for women who had been taking oral contraceptives containing drospirenone for only 3 months or less and 290% higher for women taking drospirenone-containing oral contraceptives for 7 to 12 months, compared to women taking other types of oral contraceptives.
The FDA recently updated the label for contraceptives containing drospirenone to include warnings for stopping use prior to and after surgery, and to warn that contraceptives with drospirenone may have a higher risk of dangerous blood clots.
Overdose
See also: Progestin § Overdose
Interactions
See also: Progestin § Interactions
Pharmacology
Pharmacodynamics
Drospirenone binds with high affinity to the progesterone receptor (PR) and mineralocorticoid receptor (MR), with lower affinity to the androgen receptor (AR), and with very low affinity to the glucocorticoid receptor (GR).
Progestogenic activity
Drospirenone is an agonist of the PR, the biological target of progestogens like progesterone.
Antimineralocorticoid activity
Drospirenone is an antagonist of the MR, the biological target of mineralocorticoids like aldosterone, and hence is an antimineralocorticoid.
Antiandrogenic activity
Drospirorenone is an antagonist of the AR, the biological target of androgens like testosterone and dihydrotestosterone (DHT).
Pharmacokinetics
The oral bioavailability of drospirenone is between 76 and 85%.
Chemistry
See also: Spirolactone, List of progestogens, and List of steroidal antiandrogens § Spirolactone derivatives
v t e Chemical structures of spirolactones
Progesterone
Spirolactone
Canrenone
Spironolactone
Drospirenone
Spirorenone
Chemical structures of progesterone and spirolactones (steroid-17α-spirolactones).
Drospirenone, also known as 1,2-dihydrospirorenone or as 17β-hydroxy-6β,7β:15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone, is a synthetic steroidal 17α-spirolactone, or more simply a spirolactone.
The loss of the C7α acetylthio group of spironolactone, a compound with negligible progestogenic activity,
History
Drospirenone was introduced for medical use in 2000.
Society and culture
Generic names
Drospirenone is the generic name of the drug and its INN, USAN, BAN, and JAN, while drospirénone is its DCF.
Brand names
Drospirenone is marketed in combination with an estrogen under a variety of brand names throughout the world.
Availability
Drospirenone is marketed widely throughout the world.
Litigation
In July 2012, Bayer notified its stockholders that there were more than 12,000 lawsuits against the company involving Yaz, Yasmin, and other oral contraceptives with drospirenone, and that the company by then settled 1,977 cases for US$402.6 million, for an average of US$212,000 per case, while setting aside US$610.5 million to settle the others.
As of July 17, 2015, there have been at least 4,000 lawsuits and claims still pending regarding venous thromboembolic events. This doesn’t include the roughly 10,000 claims that Bayer has already settled without admitting liability. These claims of venous thromboembolic events have amounted to US$1.97 billion. Bayer also reached a settlement for arterial thromboembolic events, including stroke and heart attacks, for US$56.9 million.
Research
Drospirenone (developmental code name LF-111) is or was under development by Leon Farma as a progestin-only pill for hormonal birth control in women, but as of March 2017 no recent reports of development have been identified.
Drospirenone (tentative brand name Estelle) is under development by Mithra Pharmaceuticals in combination with estetrol as a combined oral contraceptive for pregnancy in women.

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