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MedKoo Cat#: 414047 | Name: Epostane

Description:

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

Epostane is an inhibitor of 3β-hydroxysteroid dehydrogenase that was developed as a contraceptive, abortifacient, and oxytocic drug but was never marketed. By inhibiting 3β-HSD, epostane blocks the biosynthesis of progesterone from pregnenolone, thereby functioning as an antiprogestogen and terminating pregnancy.

Chemical Structure

Epostane
Epostane
CAS#80471-63-2

Theoretical Analysis

MedKoo Cat#: 414047

Name: Epostane

CAS#: 80471-63-2

Chemical Formula: C22H31NO3

Exact Mass: 357.2304

Molecular Weight: 357.49

Elemental Analysis: C, 73.92; H, 8.74; N, 3.92; O, 13.43

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Synonym
Epostane; Epostano; Epostanum; Win32729; Win-32729; Win 32729
IUPAC/Chemical Name
Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-4,17-dimethyl-, (4alpha,5alpha,17beta)-
InChi Key
CETKWEWBSMKADK-KTSPJTIUSA-N
InChi Code
InChI=1S/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h14-16,24-25H,5-11H2,1-4H3/t14-,15-,16-,18-,19+,20-,21-,22-/m0/s1
SMILES Code
C[C@@]12[C@@](C)(O)CC[C@@]1([H])[C@]3([H])CC[C@@]45[C@](O5)(C)C(O)=C(C#N)C[C@]4(C)[C@@]3([H])CC2
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 357.49 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: Liu CG, Lin ZM, Li WK, Wu XY, Wang ZX, Xue T, Xu RY. [Antifertility effects of mifepristone and epostane alone and in combination in rats]. Zhongguo Yao Li Xue Bao. 1993 Sep;14(5):437-40. Chinese. PMID: 8010036. 2: Martin PA, Hammitt DG, Strohbehn RS, Keister DM. Effect of epostane, a competitive inhibitor of the 3beta-hydroxysteroid dehydrogenase enzyme, in cyclic sows. Theriogenology. 1988 Oct;30(4):823-9. doi: 10.1016/0093-691x(88)90316-0. PMID: 16726523. 3: Crooij MS. Antiprogestins. Eur J Obstet Gynecol Reprod Biol. 1988 Jun;28(2):129-32. doi: 10.1016/0028-2243(88)90091-3. PMID: 3042493. 4: Espey LL, Adams RF, Tanaka N, Okamura H. Effects of epostane on ovarian levels of progesterone, 17 beta-estradiol, prostaglandin E2, and prostaglandin F2 alpha during ovulation in the gonadotropin-primed immature rat. Endocrinology. 1990 Jul;127(1):259-63. doi: 10.1210/endo-127-1-259. PMID: 2361472. 5: Martin PA, Hammitt DG, Strohbehn RS, Keister DM. Induction of parturition in swine and epostane, a competitive inhibitor of 3 beta-hydroxysteroid dehydrogenase. J Anim Sci. 1987 Feb;64(2):497-506. doi: 10.2527/jas1987.642497x. PMID: 3470276. 6: Tanaka N, Espey LL, Stacy S, Okamura H. Epostane and indomethacin actions on ovarian kallikrein and plasminogen activator activities during ovulation in the gonadotropin-primed immature rat. Biol Reprod. 1992 Apr;46(4):665-70. doi: 10.1095/biolreprod46.4.665. PMID: 1576264. 7: Snyder BW, Reel JR, Winneker RC, Batzold FH, Potts GO. Effect of epostane, ZK 98299, and ZK 98734 on the interruption of pregnancy in the rat. Biol Reprod. 1989 Mar;40(3):549-54. doi: 10.1095/biolreprod40.3.549. PMID: 2758087. 8: Webster MA, Gillmer MD. Induction of abortion in early first trimester human pregnancy using epostane. Br J Obstet Gynaecol. 1989 Mar;96(3):340-5. doi: 10.1111/j.1471-0528.1989.tb02395.x. PMID: 2713292. 9: Abortion. BIRPERHT Publ. 1993 Sep;5(2):3-7. PMID: 12345783. 10: Vanage G, Kadam PA, Bardin CW, Koide SS. Potentiating effect of epostane on pregnancy terminating activity of RU 486 in the rat. Contraception. 1993 May;47(5):499-506. doi: 10.1016/0010-7824(93)90102-d. PMID: 8513677. 11: Crooij MJ, de Nooyer CC, Rao BR, Berends GT, Gooren LJ, Janssens J. Termination of early pregnancy by the 3 beta-hydroxysteroid dehydrogenase inhibitor epostane. N Engl J Med. 1988 Sep 29;319(13):813-7. doi: 10.1056/NEJM198809293191301. PMID: 3166108. 12: Snyder BW, Schane HP. Inhibition of luteal phase progesterone levels in the rhesus monkey by epostane. Contraception. 1985 May;31(5):479-86. doi: 10.1016/0010-7824(85)90083-6. PMID: 3861290. 13: Birgerson L, Odlind V. Early pregnancy termination with antiprogestins: a comparative clinical study of RU 486 given in two dose regimens and Epostane. Fertil Steril. 1987 Oct;48(4):565-70. doi: 10.1016/s0015-0282(16)59465-5. PMID: 3653415. 14: Tanaka N, Espey LL, Kawano T, Okamura H. Comparison of inhibitory actions of indomethacin and epostane on ovulation in rats. Am J Physiol. 1991 Feb;260(2 Pt 1):E170-4. doi: 10.1152/ajpendo.1991.260.2.E170. PMID: 1996619. 15: Fu SL, Dial GD, Keister DM, Butler WR. Increased ovulation rate in gilts after oral administration of epostane. J Reprod Fertil. 1990 Sep;90(1):297-304. doi: 10.1530/jrf.0.0900297. PMID: 2231549. 16: Christin-Maitre S, Bouchard P, Spitz IM. Medical termination of pregnancy. N Engl J Med. 2000 Mar 30;342(13):946-56. doi: 10.1056/NEJM200003303421307. PMID: 10738054. 17: De Bosschere H, Ducatelle R, Tshamala M, Coryn M. The use of epostane in an attempt to reproduce cystic endometrial hyperplasia in the bitch. Vet Res Commun. 2003 Oct;27(7):527-38. doi: 10.1023/a:1026016312716. PMID: 14609264. 18: Rannevik G, Doeberl A, Valentin L. Epostane in nonpregnant females: effects on progesterone, 17 alpha-hydroxyprogesterone, and 17 beta-estradiol of two dose levels given for one month. Fertil Steril. 1988 Dec;50(6):893-902. doi: 10.1016/s0015-0282(16)60368-0. PMID: 3203752. 19: Birgerson L, Odlind V, Johansson ED. Effects of Epostane on progesterone synthesis in early human pregnancy. Contraception. 1986 Apr;33(4):401-10. doi: 10.1016/0010-7824(86)90103-4. PMID: 3731777. 20: Keister DM, Gutheil RF, Kaiser LD, D'Ver AS. Efficacy of oral epostane administration to terminate pregnancy in mated laboratory bitches. J Reprod Fertil Suppl. 1989;39:241-9. PMID: 2621726.