15690-57-0

15690-57-0 structure

Name: enclomifene
Chemical Name: trans-clomiphene
CAS Number: 15690-57-0
Molecular Formula: C₂₆H₂₈ClNO
Molecular Weight: 405.960
Catalog: Research Areas Endocrinology
Create Date: 2018-10-04 15:31:25
Modify Date: 2024-01-05 22:28:15
Enclomiphene ((E)-Clomiphene) is a potent and orally active non-steroidal estrogen receptor antagonist, with antioestrogenic property. Enclomiphene can be used for the research of ovarian dysfunction, testosterone deficiency, male hypogonadism and type 2 diabetes[1].

Name	trans-clomiphene
Synonyms	2-(4-(2-Chloro-1,2-diphenylvinyl)phenoxy)-N,N-diethylethanamine Clomiphene Zuclomiphene Isomer A Transclomifenum 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine zuclomifene Ethanamine, 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethyl- cis-clomifene 2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine cis-clomiphene enclomiphene Ethanamine, 2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethyl- Transclomiphene 1-[p-(b-Diethylaminoethoxy)phenyl]-1,2-diphenylchloroethylene Clomiphene B trans-Clomiphene (E)-Clomiphene 2-[p-(2-Chloro-1,2-diphenylvinyl)phenoxy]triethylamine (E)-2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine trans-Clomifene 2-[p-(b-Chloro-a-phenylstyryl)phenoxy]triethylamine Z-CloMiphene-d4 2-{4-[(E)-2-Chloro-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanamine 2-{4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy}-N,N-diethylethanamine

Description	Enclomiphene ((E)-Clomiphene) is a potent and orally active non-steroidal estrogen receptor antagonist, with antioestrogenic property. Enclomiphene can be used for the research of ovarian dysfunction, testosterone deficiency, male hypogonadism and type 2 diabetes[1].
Related Catalog	Signaling Pathways >> Others >> Estrogen Receptor/ERR Research Areas >> Endocrinology Research Areas >> Metabolic Disease
In Vitro	Enclomiphene (0-100 μM, 6 h) dose-dependently inhibits basal and gonadotrophin-stimulated small and large ovine luteal cell progesterone secretion[2]. Enclomiphene (0-100 μg/mL, 24 h) dose-dependently inhibits fertilization rates, blastocyst formation rates, and degeneration rates in mouse oocytes[3]. Enclomiphene (1 nM-10 μM, 6 h) dose-dependently decreases E2-induced inhibition of follicle stimulating hormone (FSH) secretion in primary sheep pituitary cells[4].
In Vivo	Enclomiphene (subcutaneous injection, 0.25 and 0.5 mg/animal, daily) inhibits spermatogenesis and decreases serum luteinizing hormone (LH) and testosterone levels in intact or castrated rats[5]. Enclomiphene (oral adminstration, 0.03-3 mg/kg, daily for 90 days) reductes body weight to sham levels, and reduced serum cholesterol[6]. Animal Model: 21 days-old Charles River male rats[5] Dosage: 0.25 and 0.5 mg/animal, daily for 24 days. Administration: Subcutaneous injection Result: Decreased LH and testosterone levels in the serum. Animal Model: OVX (ovariectomy) rat model[6] Dosage: 0.03, 1, and 3 mg/kg, daily for 90 days. Administration: Oral adminstration Result: Reducted body weight to sham levels, and reduced serum cholesterol. Showed dose-dependent effects on the proximal tibia with BMD and BMC approaching posttreatment Sham levels.
References	[1]. Rodriguez KM, et al. Enclomiphene citrate for the treatment of secondary male hypogonadism. Expert Opin Pharmacother. 2016 Aug;17(11):1561-7. [2]. M S Opsahl, et al. Effects of enclomiphene and zuclomiphene on basal and gonadotrophin-stimulated progesterone secretion by isolated subpopulations of small and large ovine luteal cells. Hum Reprod. 1996 Jun;11(6):1250-5. [3]. G E Schmidt, et al. The effects of enclomiphene and zuclomiphene citrates on mouse embryos fertilized in vitro and in vivo. Am J Obstet Gynecol. 1986 Apr;154(4):727-36. [4]. E S Huang, et al. Estrogenic and antiestrogenic effects of enclomiphene and zuclomiphene on gonadotropin secretion by ovine pituitary cells in culture. Endocrinology. 1983 Feb;112(2):442-8. [5]. R Weissenberg, et al. The effect of clomiphene citrate and its Zu or En isomers on the reproductive system of the immature male rat. Andrologia. 1992 May-Jun;24(3):161-5. [6]. R T Turner, et al. Differential responses of estrogen target tissues in rats including bone to clomiphene, enclomiphene, and zuclomiphene. Endocrinology. 1998 Sep;139(9):3712-20.

Density	1.1±0.1 g/cm3
Boiling Point	509.0±50.0 °C at 760 mmHg
Molecular Formula	C₂₆H₂₈ClNO
Molecular Weight	405.960
Flash Point	261.6±30.1 °C
Exact Mass	405.185944
PSA	12.47000
LogP	8.01
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.588

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YE0810000

CHEMICAL NAME :: Triethylamine, 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)-, (E)-

CAS REGISTRY NUMBER :: 15690-57-0

LAST UPDATED :: 198910

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C26-H28-Cl-N-O

MOLECULAR WEIGHT :: 406.00

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: AEMBAP Advances in Experimental Medicine and Biology. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.1- 1967- Volume(issue)/page/year: 138,87,1982

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