Butagest

Butagest, also known as buterol,[1] as well as 3β-hydroxy-6-methyl-17α-hydroxypregna-4,6-dien-20-one 3β-butanoate 17α-acetate or as 6-methyl-17α-hydroxy-δ6-progesterone 3β-butanoate 17α-acetate, is a steroidal progestin which was developed in Russia for potential clinical use but was never marketed.[2][3][4][5][6] It is a modification of megestrol acetate in which the C3 ketone has been replaced with a C3β butanoyloxy moiety.

Butagest
Clinical data
Other namesButerol; 17α-Acetoxy-3β-butanoyloxy-6-methyl-pregna-4,6-dien-20-one; 17α-Acetoxy-6-methyl-20-oxopregna-4,6-dien-3β-yl butyrate; 6-Methyl-17α-hydroxy-δ6-progesterone 3β-butanoate 17α-acetate
Drug classProgestogen; Progestogen ester
Identifiers
IUPAC name
  • [(3S,8R,9S,10R,13S,14S,17R)-17-Acetyl-17-acetyloxy-6,10,13-trimethyl-1,2,3,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-yl] butanoate
PubChem CID
ChemSpider
Chemical and physical data
FormulaC28H40O5
Molar mass456.623 g·mol−1
3D model (JSmol)
SMILES
  • CCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3C=C(C2=C1)C)CC[C@@]4(C(=O)C)OC(=O)C)C)C
InChI
  • InChI=1S/C28H40O5/c1-7-8-25(31)32-20-9-12-26(5)22-10-13-27(6)23(21(22)15-17(2)24(26)16-20)11-14-28(27,18(3)29)33-19(4)30/h15-16,20-23H,7-14H2,1-6H3/t20-,21+,22-,23-,26+,27-,28-/m0/s1
  • Key:VWKIFEBMJRFARL-NAEKRLSBSA-N

See also

References
  1. Fedotcheva TA, Kruglov AG, Teplova VV, Fedotcheva NI, Rzheznikov VM, Shimanovskiĭ NL (2012). "[Effect of steroid hormones on production of reactive oxygen species in mitochondria]". Biofizika. 57 (6): 1014–9. PMID 23272582.
  2. Sergeev PV, Semeĭkin AV, Smirnova ZS, et al. (2004). "[Antitumor activity of the new gestagen 17alpha-acetoxy-3beta-butanoyloxy-6-methyl-pregna-4,6-dien-20-one]". Eksp Klin Farmakol. 67 (4): 54–6. PMID 15500049.
  3. Tapil'skaia NI, Petrosian MA, Lesik EA (2002). "[Therapeutic efficacy of novel 17alpha-hydroxyprogesterone derivatives in experimental preterm labor]". Eksp Klin Farmakol. 65 (1): 44–5. PMID 12025785.
  4. Fedotcheva, T. A., Semeykin, A. V., Schimanowsky, N. L., & Rzheznikov, V. M. (2004, July). New progestin butagest is a perspective antiproliferative agent and chemosensitizer. In FUNDAMENTAL & CLINICAL PHARMACOLOGY (Vol. 18, pp. 84-84). 111 RIVER ST, HOBOKEN 07030-5774, NJ USA: WILEY-BLACKWELL.
  5. Korkhov VV, Lesik EA, Petrosian MA (2005). "[Gestagenic and contraceptive activity of new synthetic progesterone analogs in experimental animals]". Eksp Klin Farmakol. 68 (1): 39–41. PMID 15786963.
  6. Kareva EN, Grinenko GS, Gasparian ND, Ovchinnikova EV, Gorenkova OS (2006). "[Influence of the structure of synthetic gestagens on their binding to progesteron receptors in the endometrium]". Eksp Klin Farmakol. 69 (4): 36–8. PMID 16995436.



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