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MedKoo Cat#: 461362 | Name: Zuclomiphene

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Zuclomiphene is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group.

Chemical Structure

Zuclomiphene
Zuclomiphene
CAS#15690-55-8

Theoretical Analysis

MedKoo Cat#: 461362

Name: Zuclomiphene

CAS#: 15690-55-8

Chemical Formula: C26H28ClNO

Exact Mass: 405.1859

Molecular Weight: 405.96

Elemental Analysis: C, 76.92; H, 6.95; Cl, 8.73; N, 3.45; O, 3.94

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Zuclomiphene; Cisclomifenum; cis-Clomiphene;
IUPAC/Chemical Name
(Z)-2-(4-(2-chloro-1,2-diphenylvinyl)phenoxy)-N,N-diethylethan-1-amine
InChi Key
GKIRPKYJQBWNGO-QPLCGJKRSA-N
InChi Code
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-
SMILES Code
Cl/C(C1=CC=CC=C1)=C(C2=CC=C(OCCN(CC)CC)C=C2)/C3=CC=CC=C3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 405.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Young SL, Opsahl MS, Fritz MA. Serum concentrations of enclomiphene and zuclomiphene across consecutive cycles of clomiphene citrate therapy in anovulatory infertile women. Fertil Steril. 1999 Apr;71(4):639-44. PubMed PMID: 10202872. 2: Nelson EA, Barnes AB, Wiehle RD, Fontenot GK, Hoenen T, White JM. Clomiphene and Its Isomers Block Ebola Virus Particle Entry and Infection with Similar Potency: Potential Therapeutic Implications. Viruses. 2016 Aug 2;8(8). pii: E206. doi: 10.3390/v8080206. PubMed PMID: 27490565; PubMed Central PMCID: PMC4997570. 3: Young RL, Goldzieher JW, Chakraborty PK, Panko WB, Bridges CN. Qualitative differences in estrogenic/antiestrogenic effects of clomiphene and zuclomiphene. Int J Fertil. 1991 Sep-Oct;36(5):291-5. PubMed PMID: 1683658. 4: Opsahl MS, Fitz TA, Rexroad CE Jr, Fritz MA. 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. PubMed PMID: 8671435. 5: Fontenot GK, Wiehle RD, Podolski JS. Differential effects of isomers of clomiphene citrate on reproductive tissues in male mice. BJU Int. 2016 Feb;117(2):344-50. doi: 10.1111/bju.13244. Epub 2015 Sep 7. PubMed PMID: 26220499. 6: Schmidt GE, Kim MH, Mansour R, Torello L, Friedman CI. 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. PubMed PMID: 3083679. 7: Ramsey RB, Fredericks M, Fischer VW. Effect of zuclomiphene on cholesterol formation in the developing central nervous system of the rat. J Neurochem. 1977 Jun;28(6):1317-21. PubMed PMID: 874494. 8: Helo S, Mahon J, Ellen J, Wiehle R, Fontenot G, Hsu K, Feustel P, Welliver C, McCullough A. Serum levels of enclomiphene and zuclomiphene in men with hypogonadism on long-term clomiphene citrate treatment. BJU Int. 2017 Jan;119(1):171-176. doi: 10.1111/bju.13625. Epub 2016 Sep 11. PubMed PMID: 27511863. 9: Ramsey RB. Effect of hypocholesterolemic agents on central nervous system cholesterol biosynthesis III. Zuclomiphene in combination with AY9944 and triparanol. Biochem Pharmacol. 1978;27(12):1637-40. PubMed PMID: 81057. 10: Ramsey RB, Fischer VW. Effects of zuclomiphene in combination with triparanol and ay-9944 on developing rat CNS morphology and biochemistry. Acta Neuropathol. 1977 Jul 15;39(1):97-100. PubMed PMID: 70952. 11: Huang ES, Miller WL. Estrogenic and antiestrogenic effects of enclomiphene and zuclomiphene on gonadotropin secretion by ovine pituitary cells in culture. Endocrinology. 1983 Feb;112(2):442-8. PubMed PMID: 6401242. 12: Ramsey RB, McGarry JD, Fischer VW, Sarnat HB. Alteration of developing and adult rat muscle membranes by zuclomiphene and other hypocholesterolemic agents. Acta Neuropathol. 1978 Oct 13;44(1):15-9. PubMed PMID: 81585. 13: Turner RT, Evans GL, Sluka JP, Adrian MD, Bryant HU, Turner CH, Sato M. Differential responses of estrogen target tissues in rats including bone to clomiphene, enclomiphene, and zuclomiphene. Endocrinology. 1998 Sep;139(9):3712-20. PubMed PMID: 9724022. 14: Ramsey RB, Fredericks M. Effect of hypocholesterolemic agents on central nervous system cholesterol biosynthesis. I. Zuclomiphene. Biochem Pharmacol. 1977 Jun 15;26(12):1161-7. PubMed PMID: 889582. 15: Ramsey RB, Fredericks M. Effect of hypocholesterolemic agents on central nervous system cholesterol biosynthesis. II. AY-9944 and AY-9944 plus zuclomiphene. Biochem Pharmacol. 1977 Jun 15;26(12):1169-73. PubMed PMID: 70208. 16: Ghobadi C, Amer S, Lashen H, Lennard MS, Ledger WL, Rostami-Hodjegan A. Evaluation of the relationship between plasma concentrations of en- and zuclomiphene and induction of ovulation in anovulatory women being treated with clomiphene citrate. Fertil Steril. 2009 Apr;91(4):1135-40. doi: 10.1016/j.fertnstert.2008.01.058. Epub 2008 Mar 18. PubMed PMID: 18353317. 17: Ramsey RB, Fischer VW. The biochemical and morphological response of hydrolytic enzymes in the developing brain to hypocholesterolemic agents. Acta Neuropathol. 1980;49(2):89-94. PubMed PMID: 6153493. 18: Jordan VC, Haldemann B, Allen KE. Geometric isomers of substituted triphenylethylenes and antiestrogen action. Endocrinology. 1981 Apr;108(4):1353-61. PubMed PMID: 6781873. 19: Murphy LC, Sutherland RL. Antitumor activity of clomiphene analogs in vitro: relationship to affinity for the estrogen receptor and another high affinity antiestrogen-binding site. J Clin Endocrinol Metab. 1983 Aug;57(2):373-9. PubMed PMID: 6408114. 20: Ramsey RB. Effect of extended hypocholesterolemic drug treatment on peripheral and central nervous system sterol content of the rat. Lipids. 1977 Oct;12(10):841-6. PubMed PMID: 72342.