Epimestrol

• CAT Number: I026930
• CAS Number: 7004-98-0
• Molecular Formula: C19H26O3
• Molecular Weight: 302.414
• Purity: 98%
• Synonyms: Epimestrol; Epimestrolo; Epimestrolum; NSC 55975; NSC55975; NSC-55975; Org 817; Org-817; Stimovul
• Solubility: To be determined
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (8R,9S,13S,14S,16R,17S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16,17-diol
• InChI: InChI=1S/C19H26O3/c1-19-8-7-14-13-6-4-12(22-2)9-11(13)3-5-15(14)16(19)10-17(20)18(19)21/h4,6,9,14-18,20-21H,3,5,7-8,10H2,1-2H3/t14-,15-,16+,17-,18-,19+/m1/s1
• InChIKey: UHQGCIIQUZBJAE-RRQVMCLOSA-N
• SMILES: COc1cc2c([C@H]3CC[C@@]4([C@@H]([C@@H](C[C@H]4[C@@H]3CC2)O)O)C)cc1

Epimestrol is a steroidal estrogen and an estrogen ether and prodrug of 17-epiestriol. It has been used as a component of ovulation induction in combination with gonadotropin-releasing hormone.

Reference

1: Genazzani AR, Petraglia F, Mercuri N, Brilli G, Genazzani AD, Bergamaschi M, DeRamundo BM, Volpe A. Effect of steroid hormones and antihormones on hypothalamic beta-endorphin concentrations in intact and castrated female rats. J Endocrinol Invest. 1990 Feb;13(2):91-6. doi: 10.1007/BF03349515. PMID: 2139451.
2: Vera JA, Crisosto C, Leal G, Rutllant J, Schwarze E. Estudio clínico- ecográfico de la fase ovulatoria, ciclos espontáneos e inducidos, concepcionales y no concepcionales [Clinico-echographic study of the ovulatory phase, spontaneous and induced, conceptional and non conceptional cycles]. Rev Chil Obstet Ginecol. 1989;54(3):115-23. Spanish. PMID: 2490913.
3: Carreras A, Mendoza C, Osorio C. Efectos de diferentes métodos de estimulación ovárica en ratas adultas [Effects of different methods of ovarian stimulation in adult rats]. Rev Esp Fisiol. 1988 Mar;44(1):17-20. Spanish. PMID: 3140313.
4: Grcić R, Stavrić V. Efikasnost Stimovul-a u indukovanoj ovulaciji kod infertilnih zena [Efficacy of Stimovul for ovulation induction in infertile women]. Srp Arh Celok Lek. 1987 Aug-Sep;115(8-9):869-77. Serbian. PMID: 3270199.
5: Bohl M, Schubert G, Koch M, Reck G, Strecke J, Wunderwald M, Prousa R, Ponsold K. Quantitative structure-activity relationships of estrogenic steroids substituted at C14, C15. J Steroid Biochem. 1987 May;26(5):589-97. doi: 10.1016/0022-4731(87)90012-4. PMID: 3586676.
6: Luisi M, Franchi F, Bianchi S, Gravina G, Podesta A. Radio-immunoassay of salivary progesterone for monitoring ovarian function in female infertility. Ann Biol Clin (Paris). 1987;45(4):449-52. PMID: 3674548.
7: Painvain E, Barlese MG, Mastrojanni F, Bolzano G, Gaglione R, Dragone L, Ferrarotti M, Taramanni C. Ultrasound evaluation of the ovarian hyperstimulation syndrome. Acta Eur Fertil. 1987 Jan-Feb;18(1):39-43. PMID: 3115025.
8: Graf M, Specht A, Distler W. Zur Behandlung der hypothalamisch bedingten primären Amenorrhö mit Epimestrol [Treatment of hypothalamically-induced primary amenorrhea with epimestrol]. Geburtshilfe Frauenheilkd. 1986 Jul;46(7):444-9. German. doi: 10.1055/s-2008-1026661. PMID: 2944790.
9: Lomeo AM, Giambersio AM. Infertilità da insufficiente fase luteinica. II. Terapia e prognosi [Infertility due to insufficient luteal phase. II. Therapy and prognosis]. Minerva Ginecol. 1986 May;38(5):401-6. Italian. PMID: 3736998.
10: Bubenheim W, Braendle W, Bettendorf G. Schwangerschaftsrate bei Sterilitätsbehandlung in Spontan- und Therapiezyklen [Rate of pregnancy in the treatment of sterility during spontaneous and therapy cycles]. Geburtshilfe Frauenheilkd. 1985 Jul;45(7):459-61. German. doi: 10.1055/s-2008-1036352. PMID: 4029586.
11: Klimek R. Epimestrol (Stimovul) w ginekologii [Epimestrol (Stimovul) in gynecology]. Ginekol Pol. 1985 May-Jun;56(5-6):387-8. Polish. PMID: 3902585.
12: Buvat J, Buvat-Herbaut M. L’induction de l’ovulation en 1985 [Induction of ovulation in 1985]. J Gynecol Obstet Biol Reprod (Paris). 1985;14(7):899-913. French. PMID: 3937850.
13: Tolino A, Romano L, Montemagno U. Resistant ovary syndrome and fertility. Acta Eur Fertil. 1984 May-Jun;15(3):175-7. PMID: 6485708.
14: Giarola A. Indirizzi di terapia ormonale della sterilità secretoria femminile [Indications for hormone therapy of female secretory sterility]. Minerva Med. 1983 May 7;74(19):1097-126. Italian. PMID: 6341886.
15: Peris C, Lanza MG, Belforte L, Lotano MR, Prelato L. Trattamiento ciclico con MAP delle amenorree "funzionali" [Cyclic treatment of "functional" amenorrheas with MAP]. Minerva Ginecol. 1983 Apr;35(4):239-46. Italian. PMID: 6888798.
16: Zrubek H, Semczuk M, Oleszczuk J, Waroński W, Szustak J, Al-Masri MM, Kumor J. Próba oceny skuteczności Epimestrolu (Stimovul-Organon) w leczeniu braku owulacji u kobiet niepłodnych II grupy wg WHO [Evaluation of the effectiveness of Epimestrol (Stimovul-Organon) in the treatment of anovulation in group II female sterility according to the WHO classification]. Ginekol Pol. 1983 Apr;54(4):281-4. Polish. PMID: 6414892.
17: Seki K, Seki M, Kato K. Outcome of pregnancy and follow-up of children conceived by ovulation induction. Asia Oceania J Obstet Gynaecol. 1983 Mar;9(1):59-69. doi: 10.1111/j.1447-0756.1983.tb00605.x. PMID: 6860239.
18: Kicovic PM, Luisi M, Cortés-Prieto J, Franchi F. A comparative study of clomiphene and epimestrol on plasma progesterone, CBG, TBG and SHBG, and salivary progesterone levels. Reproduccion. 1982 Apr-Jun;6(2):133-40. PMID: 6890485.
19: Paoletti AM, Melis GB, De Marco F, Genazzani AR, Gargiulo T, Lanatà F, Fioretti P. Trattamento della sterilità endocrina femminile con epimestrolo [Treatment of female endocrine sterility with epimestrol]. Minerva Ginecol. 1981 Jun;33(6):520-7. Italian. PMID: 7279271.
20: Kincses L, Veres I, Farkasinszky T, Wagner A, Somogyi I, Szilárd J, Sas M. Nachuntersuchung von Kindern aus induzierten Schwangerschaften [Follow-up checks of children born from induced pregnancy (author’s transl)]. Zentralbl Gynakol. 1981;103(9):502-14. German. PMID: 7257660.