Enclomiphene citrate | trans-Clomiphene | 7599-79-3 | 15690-57-0 | estrogen receptor antagonist

MedKoo Cat#: 320101 | Name: Enclomiphene citrate

Description:

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

Enclomiphene, also known as ICI-46476, RMI-16289 and trans-Clomiphene, is a non-steroidal estrogen receptor antagonist in development for secondary hypogonadism in overweight men wishing to restore normal testicular function. Oral enclomiphene citrate raises testosterone and preserves sperm counts in obese hypogonadal men, unlike topical testosterone: restoration instead of replacement.

Chemical Structure

Enclomiphene citrate

CAS#7599-79-3 (citrate)

Theoretical Analysis

MedKoo Cat#: 320101

Name: Enclomiphene citrate

CAS#: 7599-79-3 (citrate)

Chemical Formula: C32H36ClNO8

Exact Mass: 0.0000

Molecular Weight: 598.09

Elemental Analysis: C, 64.26; H, 6.07; Cl, 5.93; N, 2.34; O, 21.40

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Related CAS #

7599-79-3 (citrate) 15690-57-0 (free base) 50-41-9 14158-65-7 (HCl)

Synonym

ICI-46476; ICI46476; ICI 46476; RMI-16289; RMI16289; RMI 16289. (E)-Clomiphene citrate; Androxal; Enclomid. Enclomiphene citrate;trans-Clomiphene citrate; trans-Clomifene citrate;

IUPAC/Chemical Name

(E)-2-(4-(2-chloro-1,2-diphenylvinyl)phenoxy)-N,N-diethylethan-1-amine 2-hydroxypropane-1,2,3-tricarboxylate

InChi Key

PYTMYKVIJXPNBD-BTKVJIOYSA-N

InChi Code

InChI=1S/C26H28ClNO.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,3-4,19-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25+;

SMILES Code

Cl/C(C1=CC=CC=C1)=C(C2=CC=C(OCCN(CC)CC)C=C2)\C3=CC=CC=C3.O=C(CC(C(O)=O)(O)CC(O)=O)O

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, not in water

Shelf Life

>2 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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 598.09 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.

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: Earl JA, Kim ED. Enclomiphene citrate: A treatment that maintains fertility in men with secondary hypogonadism. Expert Rev Endocrinol Metab. 2019 May;14(3):157-165. doi: 10.1080/17446651.2019.1612239. Epub 2019 May 7. PMID: 31063005. 2: Niederberger C. Re: Oral Enclomiphene Citrate Raises Testosterone and Preserves Sperm Counts in Obese Hypogonadal Men, Unlike Topical Testosterone: Restoration Instead of Replacement. J Urol. 2017 Jan;197(1):233. doi: 10.1016/j.juro.2016.10.018. Epub 2016 Oct 15. PMID: 27979553. 3: 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. PMID: 27511863. 4: Rodriguez KM, Pastuszak AW, Lipshultz LI. Enclomiphene citrate for the treatment of secondary male hypogonadism. Expert Opin Pharmacother. 2016 Aug;17(11):1561-7. doi: 10.1080/14656566.2016.1204294. Epub 2016 Jul 4. PMID: 27337642; PMCID: PMC5009465. 5: Kovac JR. Reproductive endocrinology: Oral enclomiphene citrate in obese men with hypogonadism. Nat Rev Urol. 2016 Mar;13(3):133-4. doi: 10.1038/nrurol.2015.311. Epub 2016 Jan 20. PMID: 26787395. 6: Kim ED, McCullough A, Kaminetsky J. Oral enclomiphene citrate raises testosterone and preserves sperm counts in obese hypogonadal men, unlike topical testosterone: restoration instead of replacement. BJU Int. 2016 Apr;117(4):677-85. doi: 10.1111/bju.13337. Epub 2015 Oct 23. PMID: 26496621. 7: Niederberger C. Re: Enclomiphene citrate stimulates testosterone production while preventing oligospermia: a randomized phase II clinical trial comparing topical testosterone. J Urol. 2015 Jun;193(6):2053-4. doi: 10.1016/j.juro.2015.03.052. Epub 2015 Mar 16. PMID: 25986825. 8: Wiehle RD, Fontenot GK, Wike J, Hsu K, Nydell J, Lipshultz L; ZA-203 Clinical Study Group. Enclomiphene citrate stimulates testosterone production while preventing oligospermia: a randomized phase II clinical trial comparing topical testosterone. Fertil Steril. 2014 Sep;102(3):720-7. doi: 10.1016/j.fertnstert.2014.06.004. Epub 2014 Jul 17. PMID: 25044085. 9: Wiehle R, Cunningham GR, Pitteloud N, Wike J, Hsu K, Fontenot GK, Rosner M, Dwyer A, Podolski J. Testosterone Restoration by Enclomiphene Citrate in Men with Secondary Hypogonadism: Pharmacodynamics and Pharmacokinetics. BJU Int. 2013 Jul 12;112(8):1188–200. doi: 10.1111/bju.12363. Epub ahead of print. PMID: 23875626; PMCID: PMC4155868. 10: Kaminetsky J, Werner M, Fontenot G, Wiehle RD. Oral enclomiphene citrate stimulates the endogenous production of testosterone and sperm counts in men with low testosterone: comparison with testosterone gel. J Sex Med. 2013 Jun;10(6):1628-35. doi: 10.1111/jsm.12116. Epub 2013 Mar 26. PMID: 23530575. 11: Kaminetsky J, Hemani ML. Clomiphene citrate and enclomiphene for the treatment of hypogonadal androgen deficiency. Expert Opin Investig Drugs. 2009 Dec;18(12):1947-55. doi: 10.1517/13543780903405608. PMID: 19938905. 12: Hill S, Arutchelvam V, Quinton R. Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men. IDrugs. 2009 Feb;12(2):109-19. PMID: 19204885. 13: 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. doi: 10.1016/s0015-0282(98)00537-8. PMID: 10202872. 14: 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. doi: 10.1210/endo.139.9.6177. PMID: 9724022. 15: 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. doi: 10.1093/oxfordjournals.humrep.a019367. PMID: 8671435. 16: Schramm RD, Roberge S, Reeves JJ. Enclomiphene does not alter the postpartum interval of suckled beef cows. J Anim Sci. 1991 Oct;69(10):4112-6. doi: 10.2527/1991.69104112x. PMID: 1778825. 17: Gregg DW, Nett TM. Effects of enclomiphene on estradiol-induced changes in LH secretion in ewes. J Anim Sci. 1990 Oct;68(10):3293-9. doi: 10.2527/1990.68103293x. PMID: 2123847. 18: Westfahl PK. Enclomiphene induces luteolysis in the nonpregnant guinea pig. Experientia. 1989 Jan 15;45(1):104-6. doi: 10.1007/BF01990463. PMID: 2492231. 19: Chang CF, Reeves JJ. Postpartum interval in beef cows shortened by enclomiphene. J Anim Sci. 1987 Jul;65(1):217-23. doi: 10.2527/jas1987.651217x. PMID: 3112086. 20: 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. doi: 10.1016/0002-9378(86)90444-8. PMID: 3083679.