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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 ZUCLOMIPHENE 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-OQKDUQJOSA-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

Description
Curator's Comment:: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C28322 https://www.ncbi.nlm.nih.gov/pubmed/3181488

Zuclomiphene Citrate is the cis isomer of clomiphene which exhibits weak estrogen agonist activity evaluated for antineoplastic activity against breast cancer. The individual isoforms are not available commercially, but Repros Therapeutics (The Woodlands, TX, USA) has separated them and is using enclomiphene citrate (ENC) in clinical trials in men with secondary hypogonadism who wish to preserve their fertility. Zuclomiphene, possessing no oestrogen antagonism at physiological concentrations, appears to have a longer biological half-life than enclomiphene, and thus may persist for long periods in the body. At high concentrations zuclomiphene can act as an oestrogen agonist. Clomiphene citrate (CC) is often used ‘off-label’ in men who have low testosterone to raise levels, it is also useful for the restoration of sperm counts in men. CC is approved by FDA and widely used in women for induction of ovulation for several conditions. CC is a mixture of two diastereoisomers, a cis isomer, zuclomiphene citrate (ZUC, 38%) and a trans isomer, ENC (62%). The two clomiphene isomers have mixed estrogenic and antiestrogenic effects that vary among species.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CLOMID

Approved Use

CLOMID is indicated for the treatment of ovulatory dysfunction in women desiring pregnancy.

Launch Date

-9.2102402E10
PubMed

PubMed

TitleDatePubMed
In vitro effects of clomiphene citrate on human endometrium.
1988 Nov
Differential effects of isomers of clomiphene citrate on reproductive tissues in male mice.
2016 Feb
Patents

Sample Use Guides

50 mg daily from day 2 of the third cycle for 5 days.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: Under in vitro conditions, zuclomiphene citrate can exert direct estrogenic effects on the endometrium but does not act as an antiestrogen or a progestagen.
In secretary human endometrium, 10(-6)M zuclomiphene citrate about doubled the basal output of PGF2 alpha and PGE2.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:18:26 UTC 2021
Edited
by admin
on Sat Jun 26 05:18:26 UTC 2021
Record UNII
UY5X264QZV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZUCLOMIPHENE CITRATE
Common Name English
NSC-151466
Code English
CLOMIPHENE A CITRATE
Common Name English
ETHANAMINE, 2-(4-((1Z)-2-CHLORO-1,2-DIPHENYLETHENYL)PHENOXY)-N,N-DIETHYL-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
ZUCLOMID
Common Name English
CIS-CLOMIPHENE CITRATE
Common Name English
(Z)-CLOMIPHENE CITRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Sat Jun 26 05:18:26 UTC 2021 , Edited by admin on Sat Jun 26 05:18:26 UTC 2021
Code System Code Type Description
CAS
7619-53-6
Created by admin on Sat Jun 26 05:18:26 UTC 2021 , Edited by admin on Sat Jun 26 05:18:26 UTC 2021
PRIMARY
FDA UNII
UY5X264QZV
Created by admin on Sat Jun 26 05:18:26 UTC 2021 , Edited by admin on Sat Jun 26 05:18:26 UTC 2021
PRIMARY
NCI_THESAURUS
C28322
Created by admin on Sat Jun 26 05:18:26 UTC 2021 , Edited by admin on Sat Jun 26 05:18:26 UTC 2021
PRIMARY
WIKIPEDIA
Zuclomiphene citrate
Created by admin on Sat Jun 26 05:18:26 UTC 2021 , Edited by admin on Sat Jun 26 05:18:26 UTC 2021
PRIMARY
PUBCHEM
3033832
Created by admin on Sat Jun 26 05:18:26 UTC 2021 , Edited by admin on Sat Jun 26 05:18:26 UTC 2021
PRIMARY
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