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Clomifene


Clomifene
Systematic (IUPAC) name
2-(4-(2-chloro-1,2-diphenylethenyl) phenoxy)-N,N-diethyl-ethanamine
Identifiers
CAS number	911-45-5
ATC code	G03GB02
PubChem	2800
DrugBank	APRD00880
Chemical data
Formula	C₂₆H₂₈Cl N O
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.	B3 (Au), X (U.S.)
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). In some countries, it is also registered for use in men. Clomiphene citrate is marketed under various trade names including Clomid, Serophene, Milophene, etc.

Additional recommended knowledge

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Mode of action

Clomifene acts by inhibiting the action of estrogen on the gonadotrope cells in the anterior pituitary gland. Since the estrogen receptors are prevented from recycling, the body perceives estrogen levels to be falsely lower than they actually are. As a result, the body releases more gonadotropin-releasing hormone from the hypothalamus, which drives the pituitary secretion of follicle-stimulating hormone (FSH), leading to a higher rate of ovulation and hence pregnancy.

Clomifene can lead to multiple ovulation, and hence increasing the chance of twins. 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.

Chemistry

Clomifene is a diastereomeric mixture of two geometric isomers, enclomifene (E-clomifene) and zuclomifene (Z-clomifene).

Adverse effects

Common adverse drug reactions associated with the use of clomifene (≥1% of patients) include: hot flashes, abdominal discomfort, visual blurring, 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] In some cases, patients have developed palinopsia.^[2]

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.

References

^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
^ Purvin VA (1995). "Visual disturbance secondary to clomiphene citrate.". Arch Ophthalmol. 113 (4): 482-4. PMID 7710399.

v • d • e Sex hormones and related agents (primarily G03, also L02, H01C) - human endogenous in CAPS
Progestogens: (receptor)	PROGESTERONE, Desogestrel, Drospirenone, Dydrogesterone, Ethisterone, Etonogestrel, Ethynodiol diacetate, Gestodene, Gestonorone, Levonorgestrel, Lynestrenol, Medroxyprogesterone, Megestrol, Norelgestromin, Norethisterone, Norethynodrel, Norgestimate, Norgestrel, Norgestrienone, Tibolone Selective progesterone receptor modulator: Asoprisnil, CDB-4124 Antiprogestogen: Mifepristone
Androgens: (receptor)	TESTOSTERONE, Androstanolone, Fluoxymesterone, Mesterolone, Methyltestosterone, (see also anabolic steroids) Antiandrogens: Bicalutamide, Cyproterone, Flutamide, Nilutamide, Spironolactone
Estrogens: (receptor)	ESTRADIOL, ESTRIOL, ESTRONE, Chlorotrianisene, Dienestrol, Diethylstilbestrol, Ethinylestradiol, Fosfestrol, Mestranol, Polyestradiol phosphate Selective estrogen receptor modulator: Bazedoxifene, Clomifene, Fulvestrant, Lasofoxifene, Raloxifene, Tamoxifen, Toremifene Aromatase inhibitor: Aminogluthetimide, Anastrozole, Exemestane, Formestane, Letrozole, Vorozole
Gonadotropins: (FSHR/LHCGR)	ovulation stim.: Clomifene, Urofollitropin Antigonadotropins: Danazol, Gestrinone
GnRH: (receptor)	agonist: Buserelin, Goserelin, Histrelin, Leuprorelin, Nafarelin, Triptorelin antagonist: Abarelix, Cetrorelix, Ganirelix

Categories: Citrates | Selective estrogen receptor modulators

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Clomifene". A list of authors is available in Wikipedia.