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Details

Stereochemistry ACHIRAL
Molecular Formula C26H28ClNO
Molecular Weight 405.9605
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ENCLOMIPHENE

SMILES

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

InChI

InChIKey=GKIRPKYJQBWNGO-OCEACIFDSA-N
InChI=1S/C26H28ClNO/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/h5-18H,3-4,19-20H2,1-2H3/b26-25+

HIDE SMILES / InChI

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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men.
2009 Feb
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 12:42:05 UTC 2021
Edited
by admin
on Sat Jun 26 12:42:05 UTC 2021
Record UNII
R6D2UI4FLS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENCLOMIPHENE
USAN   WHO-DD  
USAN  
Official Name English
ENCLOMIPHENE [USAN]
Common Name English
ETHANAMINE, 2-(4-(2-CHLORO-1,2-DIPHENYLETHENYL)PHENOXY)-N,N-DIETHYL-, (E)-
Common Name English
ISOMER-B
Code English
CLOMIPHENE TRANS-FORM
MI  
Common Name English
CLOMIPHENE TRANS-FORM [MI]
Common Name English
RMI-16,289
Common Name English
ISOMER B
Code English
RMI 16,289
Code English
ENCLOMIFENE [INN]
Common Name English
(E)-2-(P-(2-CHLORO-1,2-DIPHENYLVINYL)PHENOXY)TRIETHYLAMINE
Common Name English
RMI-16289
Code English
ENCLOMIPHENE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C481
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
Code System Code Type Description
DRUG BANK
DB06735
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
CAS
15690-57-0
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
PUBCHEM
1548953
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
ChEMBL
CHEMBL954
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
INN
2334
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
NCI_THESAURUS
C28211
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
FDA UNII
R6D2UI4FLS
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
EVMPD
SUB06521MIG
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
WIKIPEDIA
Enclomifene
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY
MERCK INDEX
M3647
Created by admin on Sat Jun 26 12:42:05 UTC 2021 , Edited by admin on Sat Jun 26 12:42:05 UTC 2021
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY