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Details

Stereochemistry ACHIRAL
Molecular Formula C26H28ClNO.C6H8O7
Molecular Weight 598.0843
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ENCLOMIPHENE CITRATE

SMILES

CCN(CC)CCOc1ccc(cc1)/C(=C(\c2ccccc2)/Cl)/c3ccccc3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

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+;

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1238
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C26H28ClNO
Molecular Weight 405.9605
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.3 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effect of clomiphene citrate treatment on endometrial estrogen and progesterone receptor induction in women.
1991 Jul
Visual disturbance secondary to clomiphene citrate.
1995 Apr
Multifactorial activities of nonsteroidal antiestrogens against leukemia.
2003
Selective estrogen receptor modulators.
2003 May
Clomiphene citrate--end of an era? A mini-review.
2005 Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Complete reversal of adult-onset isolated hypogonadotropic hypogonadism with clomiphene citrate.
2006 Nov
Use of clomiphene citrate in women.
2006 Nov
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors.
2008 Mar
Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men.
2009 Feb
Clomiphene and anti-oestrogens for ovulation induction in PCOS.
2009 Oct 7
Clomiphene citrate for unexplained subfertility in women.
2010 Jan 20
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
In Vitro Use Guide
Enclomiphene (10(-5) M) significantly reduced basal and LH-stimulated oestradiol synthesis after 2-4 days of human granulosa cells culture.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:18:28 UTC 2021
Edited
by admin
on Sat Jun 26 05:18:28 UTC 2021
Record UNII
J303A6U9Y6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENCLOMIPHENE CITRATE
USAN   WHO-DD  
USAN  
Official Name English
ENCLOMID
Brand Name English
ETHANAMINE, 2-(4-((1E)-2-CHLORO-1,2-DIPHENYLETHENYL)PHENOXY)-N,N-DIETHYL-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
ANDROXAL
Brand Name English
TRANS-CLOMIPHENE CITRATE
Common Name English
ENCLOMIPHENE CITRATE [USAN]
Common Name English
(E)-CLOMIPHENE CITRATE
Common Name English
ENCLOMIPHENE CITRATE [WHO-DD]
Common Name English
CLOMIPHENE B CITRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C61745
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
PRIMARY
ChEMBL
CHEMBL954
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
PRIMARY
EPA CompTox
7599-79-3
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
PRIMARY
EVMPD
SUB182287
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
PRIMARY
DRUG BANK
DBSALT002295
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
PRIMARY
FDA UNII
J303A6U9Y6
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
PRIMARY
CAS
7599-79-3
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
PRIMARY
PUBCHEM
6420009
Created by admin on Sat Jun 26 05:18:28 UTC 2021 , Edited by admin on Sat Jun 26 05:18:28 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY