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Clomifene, also known as clomiphene, is a medication used to treat infertility in women who do not ovulate.
Common side effects include pelvic pain and hot flushes.
Clomifene was approved for medical use in the United States in 1967.
Contents
1 Medical uses
2 Adverse effects
3 Pharmacology
3.1 Pharmacodynamics
3.2 Pharmacokinetics
4 Chemistry
5 History
6 Society and culture
6.1 Regulation
6.2 Brand names
7 Research
8 References
Medical uses
Clomifene is useful in those who are infertile due to anovulation or oligoovulation.
Clomifene has also been used with other assisted reproductive technology to increase success rates of these other modalities.
Proper timing of the drug is important; it should be taken starting on about the fifth day of the cycle, and there should be frequent intercourse.
The following procedures may be used to monitor induced cycles:
Follicular monitoring with vaginal ultrasound, starting 4–6 days after last pill. Serial transvaginal ultrasound can reveal the size and number of developing follicles. It can also provide presumptive evidence of ovulation such as sudden collapse of the preovulatory follicle, and an increase in fluid volume in the rectouterine pouch. After ovulation, it may reveal signs of luteinization such as loss of clearly defined follicular margins and appearance of internal echoes.
Serum estradiol levels, starting 4–6 days after last pill
Post-coital test 1–3 days before ovulation to check whether there are at least 5 progressive sperm per HPF
Adequacy of LH surge by urine LH surge tests 3 to 4 days after last clomifene pill
Mid-luteal progesterone, with at least 10 ng/ml 7–9 days after ovulation being regarded as adequate.
Repeat dosing: This 5-day treatment course can be repeated every 30 days. The dosage may be increased by 50-mg increments in subsequent cycles until ovulation is achieved.
It is no longer recommended to perform an ultrasound examination to exclude any significant residual ovarian enlargement before each new treatment cycle.
Clomifene is sometimes used in the treatment of male hypogonadism as an alternative to testosterone replacement therapy.
Clomifene has been used in the treatment of gynecomastia.
Adverse effects
The most common adverse drug reaction associated with the use of clomifene (>10% of people) is reversible ovarian enlargement.
Less common effects (1-10% of people) include visual symptoms (blurred vision, double vision, floaters, eye sensitivity to light, scotomata ), headaches, vasomotor flushes (or hot flashes ), light sensitivity and pupil constriction, abnormal uterine bleeding and/or abdominal discomfort.
Rare adverse events (<1% of people) include: high blood level of triglycerides, liver inflammation, reversible baldness and/or ovarian hyperstimulation syndrome. Clomifene can lead to multiple ovulation, hence increasing the chance of twins (10% of births instead of ~1% in the general population) and triplets. Some studies have suggested that clomifene citrate if used for more than a year may increase the risk of ovarian cancer. Subsequent studies have failed to corroborate those findings. The incidence of fetal and neonatal abnormalities for patients on clomifene for fertility is similar to that seen in the general population. There is no data to suggest a higher rate of congenital anomalies or spontaneous abortions after using this drug. Compared to letrozole, another drug used for ovarian stimulation, a study found no significant difference in the rate of overall abnormalities, but found that congenital cardiac anomalies was significantly higher in the clomifene group compared to the letrozole group. Pharmacology Pharmacodynamics Clomifene is a nonsteroidal SERM that inhibits estrogen receptors in the hypothalamus, inhibiting negative feedback of estrogen on gonadotropin release, leading to up-regulation of the hypothalamic–pituitary–gonadal axis. Zuclomifene, a more active isomer, stays bound for longer periods of time. In normal physiologic female hormonal cycling, at 7 days past ovulation, high levels of estrogen and progesterone produced from the corpus luteum inhibit GnRH, FSH and LH at the hypothalamus and anterior pituitary. If fertilization does not occur in the post-ovulation period the corpus luteum disintegrates due to a lack of beta- hCG. This would normally be produced by the embryo in the effort of maintaining progesterone and estrogen levels during pregnancy. Therapeutically, clomifene is given early in the menstrual cycle. It is typically prescribed beginning on day 3 and continuing for 5 days. By that time, FSH level is rising steadily, causing development of a few follicles. Follicles in turn produce the estrogen, which circulates in serum. In the presence of clomifene, the body perceives a low level of estrogen, similar to day 22 in the previous cycle. Since estrogen can no longer effectively exert negative feedback on the hypothalamus, GnRH secretion becomes more rapidly pulsatile, which results in increased pituitary gonadotropin (FSH, LH) release. (More rapid, lower amplitude pulses of GnRH lead to increased LH/FSH secretion, while more irregular, larger amplitude pulses of GnRH leads to a decrease in the ratio of LH/FSH.) Increased FSH level causes growth of more ovarian follicles, and subsequently rupture of follicles resulting in ovulation. Ovulation occurs most often 6–7 days after a course of clomifene. Clomifene has been found to decrease insulin-like growth factor 1 levels in women. Pharmacokinetics Clomifene produces N -desmethylclomifene, clomifenoxide (clomifene N -oxide), and 4-hydroxyclomifene as metabolites. Chemistry Clomifene is a triphenylethylene derivative. It is a mixture of two geometric isomers, enclomifene ( (E) -clomifene) and zuclomifene ( (Z) -clomifene). These two isomers have been found to contribute to the mixed estrogenic and antiestrogenic properties of clomifene. Enclomifene Zuclomifene History A team at William S. Merrell Chemical Company led by Frank Palopoli synthesized clomifene in 1956; after its biological activity was confirmed a patent was filed and issued in November 1959. Clinical studies were conducted under an Investigational New Drug Application; it was third drug for which an IND had been filed under the 1962 Kefauver Harris Amendment to the Federal Food, Drug, and Cosmetic Act that had been passed in response to the thalidomide tragedy. The drug is widely considered to have been a revolution in the treatment of female infertility, the beginning of the modern era of assisted reproductive technology, and the beginning of what in the words of Eli Y. Adashi, was "the onset of the US multiple births epidemic". The company was acquired by Dow Chemical in 1980, Society and culture Regulation Clomifene is included on the World Anti-Doping Agency list of illegal doping agents in sport. Brand names Clomifene is marketed under many brand names worldwide, including Beclom, Bemot, Biogen, Blesifen, Chloramiphene, Clomene, ClomHEXAL, Clomi, Clomid, Clomidac, Clomifen, Clomifencitrat, Clomifene, Clomifène, Clomifene citrate, Clomifeni citras, Clomifeno, Clomifert, Clomihexal, Clomiphen, Clomiphene, Clomiphene Citrate, Cloninn, Clostil, Clostilbegyt, Clovertil, Clovul, Dipthen, Dufine, Duinum, Fensipros, Fertab, Fertec, Fertex, Ferticlo, Fertil, Fertilan, Fertilphen, Fertin, Fertomid, Ferton, Fertotab, Fertyl, Fetrop, Folistim, Genoclom, Genozym, Hete, I-Clom, Ikaclomin, Klofit, Klomen, Klomifen, Lomifen, MER 41, Milophene, Ofertil, Omifin, Ova-mit, Ovamit, Ovinum, Ovipreg, Ovofar, Ovuclon, Ovulet, Pergotime, Pinfetil, Profertil, Prolifen, Provula, Reomen, Serofene, Serophene, Serpafar, Serpafar, Surole, Tocofeno, and Zimaquin. Research Clomifene was studied for treatment and prevention of breast cancer, but issues with toxicity led to abandonment of this indication, as did the discovery of tamoxifen.

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