Clomifene
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Clomifene
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| Systematic (IUPAC) name | |
| 2-(4-(2-chloro-1,2-diphenylethenyl) phenoxy)-N,N-diethyl-ethanamine |
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| Identifiers | |
| CAS number | |
| ATC code | G03 |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C26H28ClNO |
| Mol. mass | 406 or 598.10 (with citrate) |
| Pharmacokinetic data | |
| Bioavailability | High (>90%) |
| Metabolism | Hepatic (with enterohepatic circulation) |
| Half life | 5-7 days |
| Excretion | Mainly renal, some biliary |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status |
S4 (Au), POM (UK), ℞-only (U.S.) |
| Routes | 50 mg tablets |
Clomifene (INN) or clomiphene (USAN and former BAN) or Clomid or Clomifert is a selective estrogen receptor modulator (SERM), used mainly in female infertility due to anovulation (e.g. due to polycystic ovary syndrome). Clomiphene citrate is marketed under various trade names including Clomid, Serophene, Milophene, etc.
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[edit] Mode of action
Clomifene acts by inhibiting the action of estrogen on the hypothalamus. Zuclomifene, the more active isomer (see below), binds to estrogen receptors and stays bound for long periods of time. This prevents normal receptor recycling and causes an effective reduction in hypothalamic estrogen receptor number. Since estrogen can no longer effectively feedback on the hypothalamus, GnRH secretion becomes more pulsatile, which results in increased pituitary gonadotropin (FSH, LH) release. Increased gonadotropin levels cause growth of the ovarian follicle, followed by follicular rupture, otherwise known as ovulation.
Clomifene can lead to multiple ovulation, and hence increasing the chance of twins (3-5% of births instead of normal ~1%). In comparison to purified FSH, the rate of ovarian hyperstimulation syndrome is low. There may be an increased risk of ovarian cancer and weight gain.
[edit] Chemistry
Clomifene is a diastereomeric mixture of two geometric isomers, enclomifene (E-clomifene) and zuclomifene (Z-clomifene).
Enclomifene
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Zuclomifene
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[edit] Adverse effects
Common adverse drug reactions associated with the use of clomifene (≥1% of patients) include: hot flashes, abdominal discomfort, visual blurring (dose-dependent), and/or reversible ovarian enlargement and cyst formation. Infrequent adverse effects (0.1–1% of patients) include: abnormal uterine bleeding, nausea, and/or vomiting. Rare adverse effects (<0.1% of patients) include: reversible alopecia and/or ovarian hyperstimulation syndrome.[1]
[edit] Use in bodybuilding
Clomifene is commonly used by male anabolic steroid users to bind the estrogen receptors in their bodies, thereby blocking the effects of estrogen, i.e., gynecomastia. It also restores the body's natural production of testosterone. It is commonly used as a "recovery drug" and taken toward the end of a steroid cycle.[citation needed] Some users report that taking Clomid increases the amount of fluid produced during ejaculation.[2]
[edit] References
- ^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
- ^ http://www.professionalmuscle.com/forums/showthread.php?p=470416
[edit] External links
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