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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 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.

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

Contents

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

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