Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C26H28ClNO.C6H8O7 |
| Molecular Weight | 598.083 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.CCN(CC)CCOC1=CC=C(C=C1)C(=C(\Cl)C2=CC=CC=C2)\C3=CC=CC=C3
InChI
InChIKey=PYTMYKVIJXPNBD-BTKVJIOYSA-N
InChI=1S/C26H28ClNO.C6H8O7/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,3-4,19-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25+;
| Molecular Formula | C26H28ClNO |
| Molecular Weight | 405.96 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
| Molecular Formula | C6H8O7 |
| Molecular Weight | 192.1235 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Enclomiphene (Androxal), in development by Repros Therapeutics Inc, is a non-steroidal estrogen receptor antagonist that promotes gonadotropin-dependent testosterone secretion by the testes. Enclomiphene constitutes the trans-stereoisomer of clomiphene citrate, a drug that has been widely prescribed for several decades for the treatment of female ovulatory dysfunction. Because of the antagonistic effects of enclomiphene, the drug has the potential to increase serum testosterone levels in men with secondary hypogonadism by restoring physiological endogenous testosterone secretion while maintaining testicular volume and, potentially, spermatogenesis. In clinical trials conducted to date, enclomiphene demonstrated significant efficacy in the physiological restoration of testosterone levels in males with secondary hypogonadism. The compound also exhibited an unanticipated favorable effect on fasting plasma glucose; this result has been accompanied by rapidly accumulating evidence from other researchers for a bidirectional relationship between low serum testosterone and obesity/metabolic syndrome (syndrome X) in men.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Clomiphene citrate for unexplained subfertility in women. | 2010-01-20 |
|
| Clomiphene and anti-oestrogens for ovulation induction in PCOS. | 2009-10-07 |
|
| Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men. | 2009-02 |
|
| Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors. | 2008-03 |
|
| Complete reversal of adult-onset isolated hypogonadotropic hypogonadism with clomiphene citrate. | 2006-11 |
|
| Use of clomiphene citrate in women. | 2006-11 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Clomiphene citrate--end of an era? A mini-review. | 2005-08 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Selective estrogen receptor modulators. | 2003-05 |
|
| Multifactorial activities of nonsteroidal antiestrogens against leukemia. | 2003 |
|
| Visual disturbance secondary to clomiphene citrate. | 1995-04 |
|
| Effect of clomiphene citrate treatment on endometrial estrogen and progesterone receptor induction in women. | 1991-07 |
Patents
Sample Use Guides
Oral, 12.5 mg capsule, taken once daily. Dose may be increased from 12.5 mg to 25 mg if indicated
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:00:55 GMT 2025
by
admin
on
Mon Mar 31 18:00:55 GMT 2025
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| Record UNII |
J303A6U9Y6
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C1821
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C61745
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CHEMBL954
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DTXSID80226887
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SUB182287
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DBSALT002295
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J303A6U9Y6
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7599-79-3
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100000168729
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CD-11
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6420009
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ACTIVE MOIETY |
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