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 | |
| Identifiers | |
| CAS number | |
| ATC code | G03 |
| PubChem | |
| DrugBank | |
| 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 (US) |
| Legal status |
S4 (Au), POM (UK), ℞-only (U.S.) |
| Routes | 50 mg tablets |
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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.
Mode of action
Clomifene acts by inhibiting the action of estrogen on the gonadotrope cells in the anterior pituitary gland. In response to low estrogen levels, follicle-stimulating hormone (FSH) release is increased, 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).
 Enclomifene |  Zuclomifene |
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.[1]
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
External links
de:Clomifen
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
