enclomifene

Names

[ Name ]:
enclomifene

[Synonym ]:
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

Biological Activity

[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.

Chemical & Physical Properties

[ 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

Toxicological Information

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