Clomifene
Clomifene
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<catset>Category="Citrates"</catset><catset>Category="Selective estrogen receptor modulators"</catset><right><p><table border=1 cellpadding=3 cellspacing=0 width=250 style=" border-collapse: collapse; margin: 0 0 0 0.5em"><tr><td bgcolor=ffffff align=center colspan=2> [image]<br><i>Clomifene</i></td></tr><tr><td align=center colspan=2><i>(E,Z)-2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-<br>N,N-diethyl-ethanamine</i></td></tr><tr align=center style=" border-bottom: 3px solid gray"><td><b><a href="CAS registry number">CAS number</a></b><br>911-45-5 or 50-41-9</td><td><b><a href="Anatomical Therapeutic Chemical Classification System">ATC code</a></b><br>G03GB02 </td></tr><tr><td bgcolor=eeeeee><a href="Chemical formula">Chemical formula</a></td><td bgcolor=ddeeff>C<sub>26</sub>H<sub>28</sub>ClNO</td></tr><tr><td bgcolor=eeeeee><a href="Molecular mass">Molecular weight</a></td><td bgcolor=ddeeff>406 (without citrate)<br>598.10 (with citrate)</td></tr><tr><td bgcolor=eeeeee><a href="Bioavailability">Bioavailability</a></td><td bgcolor=ddeeff>High (&gt;90%)</td></tr><tr><td bgcolor=eeeeee>Metabolism</td><td bgcolor=ddeeff>Hepatic (with enterohepatic circulation)</td></tr><tr><td bgcolor=eeeeee><a href="Half-life">Elimination half life</a></td><td bgcolor=ddeeff>5-7 days</td></tr><tr><td bgcolor=eeeeee><a href="Excretion">Excretion</a></td><td bgcolor=ddeeff>Mainly renal, some biliary</td></tr><tr><td bgcolor=eeeeee><a href="Pregnancy category">Pregnancy category</a> </td><td bgcolor=ddeeff>X (USA)</td></tr><tr><td bgcolor=eeeeee><a href="Controlled Substances Act">Legal status</a></td><td bgcolor=ddeeff>N/A</td></tr><tr><td bgcolor=eeeeee>Delivery</td><td bgcolor=ddeeff>50 mg tablets</td></tr></table><p></right> <b>Clomifene</b> or <b>clomifene citrate</b> (old name <b>clomiphene</b>, sold as ClomidŽ, SeropheneŽ, MilopheneŽ and many others) is a <a href="Selective estrogen receptor modulator">Selective estrogen receptor modulator</a> (SERM), used mainly in female <a href="Infertility">Infertility</a> due to <a href="Anovulation">Anovulation</a> (e.g. due to <a href="Polycystic ovary syndrome">Polycystic ovary syndrome</a>). In some countries, it is also registered for use in men.<p>Clomifene is a racemic mixture of two <a href="Geometric isomerism">geometric isomers</a>, enclomifene and zuclomifene.<p>Clomifene acts by inhibiting the action of <a href="Estrogen">Estrogen</a> on the <a href="Gonadotrope">Gonadotrope</a> cells in the anterior <a href="Pituitary gland">Pituitary gland</a>. "Sensing" low estrogen levels, <a href="Follicle-stimulating hormone">Follicle-stimulating hormone</a> release is increased, leading to a higher rate of <a href="Ovulation">Ovulation</a> and hence <a href="Pregnancy">Pregnancy</a>.<p>Clomifene can lead to multiple ovulation, and hence increasing the risk of <a href="Twin">twins</a>. In comparison to purified FSH, the rate of <a href="Ovarian hyperstimulation syndrome">Ovarian hyperstimulation syndrome</a> is low. There may be an increased risk of <a href="Ovarian cancer">Ovarian cancer</a>, and weight gain.