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Key Documents

SML0719

Sigma-Aldrich

Enclomiphene hydrochloride

≥96% (HPLC)

Synonym(s):

(E)-Clomiphene hydrochloride, 2-[4-[(1E)-2-Chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethyl-ethanamine hydrochloride, 2-[p-(2-Chloro-trans-1,2-diphenylvinyl)phenoxy]triethylamine hydrochloride, ICI 46476, trans-Clomifene hydrochloride, trans-Clomiphene hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C26H28ClNO · HCl
CAS Number:
Molecular Weight:
442.42
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

Assay

≥96% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

H2O: 10 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C26H28ClNO.ClH/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;1H/b26-25+;

InChI key

KKBZGZWPJGOGJF-BTKVJIOYSA-N

Biochem/physiol Actions

Enclomiphene is a non-steroidal estrogen receptor antagonist that promotes gonadotropin-dependent testosterone secretion by the testes. Enclomiphene is the trans-isomer of clomiphene, which is about a 60-40 mix of trans (Enclomiphene) and cis (Zuclomiphene). While enclomiphene (trans-clomiphene) is an estrogen antagonist, zuclomiphene (cis-clomiphene) is a mixed agonist, responsible for the estrogenic activity and therefore the common side effects sometimes seen in males. The enclomiphene isomer is responsible for the anti-estrogen activity and the restoration of ones hypothalamic–pituitary–gonadal axis. In recent clinical trials, enclomiphene increased serum LH and FSH with concomitant increases in testosterone in men with secondary hypogonadism. Enclomiphene showed overall better results than testosterone gels, which raise serum testosterone but can lower LH and FSH at the same time.

Other Notes

Light sensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Ahmad Mahran et al.
The Journal of clinical endocrinology and metabolism, 98(10), 4170-4175 (2013-08-28)
Elevated serum anti-Müllerian hormone (AMH) concentration in women with polycystic ovarian syndrome (PCOS) is known to lower sensitivity of ovarian follicles to circulating FSH. This effect may compromise the outcome of clomiphene citrate (CC) ovulation induction. The objective of the
M Sunj et al.
Human reproduction (Oxford, England), 28(9), 2417-2424 (2013-07-04)
Does unilateral volume-adjusted laparoscopic diathermy increase the chances of ovulation in women with polycystic ovary syndrome (PCOS)? Although unilateral laparoscopic ovarian drilling (ULOD) using adjusted thermal doses was more efficient than bilateral laparoscopic ovarian drilling (BLOD) using fixed doses, the
Renato Pasquali et al.
Frontiers of hormone research, 40, 83-102 (2013-09-05)
From the conceptual point of view, there are several reasons to expect that improvement of insulin sensitivity may produce several benefits in the treatment of a complex disorder like polycystic ovary syndrome (PCOS), including a decrease in insulin and androgen
Young Eun Jeon et al.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology, 29(9), 834-838 (2013-07-19)
Although a variety of factors have been reported as affecting pregnancy rates after intrauterine insemination (IUI), there have been conflicting results on prognostic factors. This study aimed to determine predictive factors for pregnancy in patients undergoing the first four IUI
Simon McDowell et al.
The Australian & New Zealand journal of obstetrics & gynaecology, 53(4), 395-398 (2013-07-09)
Clomiphene citrate is a widely used treatment for ovulatory dysfunction in women seeking pregnancy. The major adverse consequence of clomiphene use is the increased risk of multiple and higher-order multiple pregnancy. Mechanisms for multiple pregnancy include dosing variation, adjuvant therapies

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