ENCLOMIPHENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H28ClNO
Molecular Weight	405.96
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCOC1=CC=C(C=C1)C(=C(\Cl)C2=CC=CC=C2)\C3=CC=CC=C3

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	405.96
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://reprosrx.com/enclomiphene.php | http://www.medscape.com/viewarticle/854288 | https://www.ncbi.nlm.nih.gov/pubmed/19204885

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor 75 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19204885 \| https://www.ncbi.nlm.nih.gov/pubmed/6408114	Antagonist 2778		3.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Secondary hypogonadism 2 Sources: https://clinicaltrials.gov/ct2/show/NCT01534208 http://reprosrx.com/enclomiphene.php	Primary		Phase III 656	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY445219	https://www.001chemical.com/chem/search?q=DY445219
1PlusChem LLC	1P001PJ2	https://www.1pchem.com/search?query=1P001PJ2
AK Scientific	J10248	https://aksci.com/item_detail.php?cat=J10248
AK Scientific	V0188	https://aksci.com/item_detail.php?cat=V0188
Alfa Chemistry	65544	http://www.alfa-chemistry.com/search.aspx?q=65544
Alfa Chemistry	ACM14158657	http://www.alfa-chemistry.com/search.aspx?q=ACM14158657
Alfa Chemistry	ACM43054451	http://www.alfa-chemistry.com/search.aspx?q=ACM43054451
BOC Sciences	14158-65-7	http://www.bocsci.com/description.asp?cas=14158-65-7
BOC Sciences	15690-57-0	http://www.bocsci.com/description.asp?cas=15690-57-0
BOC Sciences	43054-45-1	http://www.bocsci.com/description.asp?cas=43054-45-1
BioSynth	Q-200878	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-200878
Chem Scene	CS-0088565	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0088565
Chem Scene	CS-2577	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2577
ChemShuttle	102627	https://www.chemshuttle.com/catalogsearch/result/?q=102627
ChemShuttle	151729	https://www.chemshuttle.com/catalogsearch/result/?q=151729
Excenen	EX-A2939	http://www.excenen.com/searchresultlist.php?id=EX-A2939
KeyOrganics	AS-13733	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-13733
Lab Network	LN01264096	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01264096
MedChem Express	HY-118861A	https://www.medchemexpress.com/search.html?q=HY-118861A&ft=&fa=&fp=
MedChem Express	HY-B0463	https://www.medchemexpress.com/search.html?q=HY-B0463&ft=&fa=&fp=
MolPort	MolPort-046-788-400	https://www.molport.com/shop/molecule-link/MolPort-046-788-400
Molcore	MC445219	http://www.molcore.com/CatMC445219.html
MuseChem	A000975	https://www.musechem.com/product/A000975.html
MuseChem	I006668	https://www.musechem.com/product/I006668.html
MuseChem	R018457	https://www.musechem.com/product/R018457.html
MuseChem	R051511	https://www.musechem.com/product/R051511.html
Princeton BioMolecular Research	OSSM_154395	http://www.princetonbio.com/order_online?common_id=OSSM_154395
TargetMol	T7313	https://www.targetmol.com/search?keyword=T7313
Tetrahedron	TS74954	http://www.thsci.com/search.do?q=TS74954
Toronto Research Chemicals	C587015	https://www.trc-canada.com/product-detail/?CatNum=C587015
Toronto Research Chemicals	C587025	https://www.trc-canada.com/product-detail/?CatNum=C587025
Toronto Research Chemicals	C587035	https://www.trc-canada.com/product-detail/?CatNum=C587035
Vitas-M Laboratory	STK525981	http://www.vitasmlab.biz/search/STK525981
eMolecules	171537967	https://orderbb.emolecules.com/search/#?query=171537967
eMolecules	300835856	https://orderbb.emolecules.com/search/#?query=300835856
eMolecules	45955751	https://orderbb.emolecules.com/search/#?query=45955751
eMolecules	46479064	https://orderbb.emolecules.com/search/#?query=46479064
eMolecules	50550705	https://orderbb.emolecules.com/search/#?query=50550705
mcule	MCULE-1599707603	https://mcule.com/MCULE-1599707603/
mcule	MCULE-1611494400	https://mcule.com/MCULE-1611494400/
mcule	MCULE-3924797904	https://mcule.com/MCULE-3924797904/
mcule	MCULE-4845633713	https://mcule.com/MCULE-4845633713/

PubMed

Title	Date	PubMed
Effect of clomiphene citrate treatment on endometrial estrogen and progesterone receptor induction in women.	1991 Jul	1906682
Visual disturbance secondary to clomiphene citrate.	1995 Apr	7710399
Multifactorial activities of nonsteroidal antiestrogens against leukemia.	2003	14585326
Selective estrogen receptor modulators.	2003 May	12911186
Clomiphene citrate--end of an era? A mini-review.	2005 Aug	15878925
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Complete reversal of adult-onset isolated hypogonadotropic hypogonadism with clomiphene citrate.	2006 Nov	17070201
Use of clomiphene citrate in women.	2006 Nov	17055820
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors.	2008 Mar	18320435
Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men.	2009 Feb	19204885
Clomiphene and anti-oestrogens for ovulation induction in PCOS.	2009 Oct 7	19821295
Clomiphene citrate for unexplained subfertility in women.	2010 Jan 20	20091498

Patents

Sample Use Guides

In Vivo Use Guide

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 Dec 16 17:18:19 GMT 2023` Edited by `admin` on `Sat Dec 16 17:18:19 GMT 2023`
Record UNII	R6D2UI4FLS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENCLOMIPHENE

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

ENCLOMIFENE

Official Name

English

CLOMIPHENE TRANS-FORM

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

ICI-46476

Code

English

RMI-16289

Code

English

Enclomiphene [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C481