Butagest

Butagest
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
Synonyms	Buterol; 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
PubChem (CID)	15816431
ChemSpider	21377535
Chemical and physical data
Formula	C₂₈H₄₀O₅
Molar mass	456.623 g/mol
3D model (Jmol)	Interactive image
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

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 that 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.

References

↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.

Progesterone receptor modulators

Agonists	Progesterone derivatives: 5α-Dihydroprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 16α-Hydroxyprogesterone 20α-Dihydroprogesterone Dimepregnen Diosgenin Progesterone Quingestrone Retroprogesterone derivatives: Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives: 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Anagestone Anagestone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Flumedroxone Flumedroxone acetate Gestaclone Haloprogesterone Hydromadinone (hydromadinone acetate) Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone 19-Norprogesterone derivatives: 19-Norprogesterone Amadinone Amadinone acetate Demegestone Gestadienol Gestonorone caproate (gestronol hexanoate) Gestronol (gestonorone) Nomegestrol Nomegestrol acetate Norgestomet Org-2058 Oxogestone Oxogestone phenpropionate Promegestone Segesterone Segesterone acetate (nestorone) Trimegestone Testosterone derivatives: 6,6-Difluoronorethisterone 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione Δ^4-Tibolone Allylestrenol Altrenogest Bolandiol Bolandiol dipropionate Bolandione Chloroethynyl norgestrel Cingestol Danazol Desogestrel Dienedione Dienogest Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethisterone Dimethyltrienolone Ethisterone Ethyldienolone Ethylestrenol (ethylnandrol) Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Methyldienolone Metribolone (R-1881) Metynodiol Metynodiol diacetate Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norelgestromin Norethisterone (norethindrone) Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Normethandrone (methylestrenolone, normethandrolone, normethisterone) Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tetrahydrogestrinone Tibolone Tigestol Tosagestin Trenbolone (trienolone) Trestolone Trestolone acetate Spirolactone derivatives: Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate SC-5233 SC-8109 Spironolactone Spirorenone Non-steroidal: 3,8-Dihydrodiligustilide Riligustilide Tanaproget ZM-182345

Mixed (SPRMs)	Apigenin Asoprisnil Asoprisnil ecamate Guggulsterone Kaempferol J1042 LG-120838 Naringenin PRA-910 Syringic acid Telapristone Antagonistic: Mifepristone Org-31710 Org-33628 Ulipristal acetate ZK-137316

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Lilopristone Lonaprisan Onapristone Toripristone Valproic acid Vilaprisan Zanoterone ZM-150271 ZM-172406

mPRs
(PAQRs)

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 11-Deoxycorticosterone 17α-Hydroxyprogesterone 17α,21-Dihydroxyprogesterone 21-Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone

Antagonists	Mifepristone

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Steroid hormone metabolism modulators

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