Acetomepregenol

{{Short description|Chemical compound}}

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| 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] acetate

| image = Acetomepregenol.svg

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| tradename = Diamol

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| class = Progestogen; Progestin; Progestogen ester

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| CAS_number = 3116-07-2

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| ATCvet =

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| PubChem = 197015

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| ChemSpiderID = 170630

| UNII = 1JI0G99BDO

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| synonyms = ACM; Mepregenol diacetate; Diamol; Megestrol diacetate; Megestrol 3β,17α-diacetate; 3β,17α-Diacetoxy-6-methylpregna-4,6-dien-20-one; 6-Methylpregna-4,6-dien-3β,17α-diol-20-one diacetate

| C=26 | H=36 | O=5

| SMILES = CC1=CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(CC4)OC(=O)C)C

| StdInChI_Ref =

| StdInChI = 1S/C26H36O5/c1-15-13-20-21(24(5)10-7-19(14-23(15)24)30-17(3)28)8-11-25(6)22(20)9-12-26(25,16(2)27)31-18(4)29/h13-14,19-22H,7-12H2,1-6H3/t19-,20+,21-,22-,24+,25-,26-/m0/s1

| StdInChIKey_Ref =

| StdInChIKey = SDHHPVPFUVQWKY-AVHYYFBHSA-N

}}

Acetomepregenol (ACM), also known as mepregenol diacetate and sold under the brand name Diamol, is a progestin medication which is used in Russia for the treatment of gynecological conditions and as a method of birth control in combination with an estrogen.{{cite journal | vauthors = Korkhov VV | title = [Current trends in the development of oral contraception] | language = ru | journal = Farmakologiia i Toksikologiia | volume = 48 | issue = 4 | pages = 119–122 | year = 1985 | pmid = 3899717 }}{{cite journal | vauthors = Nikitina GV, Savchenko ON, Stepanov MG | title = [Hormonal properties of new 17 alpha-hydroxyprogesterone derivatives] | language = ru | journal = Problemy Endokrinologii | volume = 33 | issue = 3 | pages = 60–63 | year = 1987 | pmid = 3116530 }}{{cite journal | vauthors = Sidel'nikova VM, Demidova EM, Borisova I, Dondukova TM, Absava GI, Korkhov VV | title = [The use of acetomepegrenol in the therapy of threatened abortion] | language = ru | journal = Akusherstvo I Ginekologiia | issue = 9 | pages = 37–40 | date = September 1990 | pmid = 2278305 }}{{cite journal| vauthors = Grinenko GS, Popova EV, Korkhov VV, Lesik EA, Petrosyan MA, Topil'skaya NI |title=Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one|journal=Pharmaceutical Chemistry Journal|issn=1573-9031|pages=113–114|volume=34|issue=3|date=March 2000|doi=10.1007/BF02524577 |s2cid=44235508|quote=Note that 3,17-diacetoxy-6-methylpregna-4,6-dien-20-one (1b), a structural analog of compound 1a, is certified in Russia under the trade name acetomepregnol and recommended for therapeutic purposes in gynecological practice and as a contraceptive preparation in combination with estrogens [4].}}{{cite journal| vauthors = Mashkovskii MD |title=Eightieth Anniversary of the Drug Chemistry Center/All-Russian Pharmaceutical Chemistry Scientific Research Institute|journal=Pharmaceutical Chemistry Journal|issn=1573-9031|pages=677–680|volume=34|issue=12|doi=10.1023/A:1010416205068|date=December 2000|s2cid=24703856}}{{cite journal| vauthors = Sergeev PV, Rzheznikov VM, Korkhov VV, Grinenko GS, Semeikin AV, Mayatskaya EE, Samoilikov RV, Shimanovskii NL | display-authors = 6 | title = Investigation of the gestagen activity of 17α-acetoxy-3β-butanoyloxy-6-methylpregna-4, 6-dien-20-one. | journal = Pharmaceutical Chemistry Journal | volume = 39 | issue = 7 | pages = 358–360 |date=July 2005| doi = 10.1007/s11094-005-0154-4 |s2cid=35450212|quote=Gestagens are widely used in medicine as drugs for the treatment of breast and uterine tumors, endometriosis, uterine bleeding, and premenstrual syndrome, as a means of hormonal therapy and maintenance of pregnancy, and as contraceptives [1, 2]. In clinics, drugs of this group are represented by acetomepregenol (AMP), medroxyprogesterone acetate (MPA), levonorgestrel, progesterone, didrogesterone, etc. [1].}}{{cite journal| vauthors = Zeinalov OA, Yaderets VV, Stytsenko TS, Petrosyan MA, Andryushina VA |title=Synthesis and biological activity of synthetic 17α-hydroxyprogesterone derivatives|journal=Pharmaceutical Chemistry Journal|date=July 2012|issn=1573-9031|pages=203–206|volume=46|issue=4|doi=10.1007/s11094-012-0761-9 |s2cid=7159432}} It has also been studied in the treatment of threatened abortion. It has been used in veterinary medicine as well.{{cite conference | vauthors = Bratanov K, Bankov N, Doichev S, Pisheva M, Klinskii IU, Zhirkov G | date = 1981 | title = Action of diacetate mepregnol (diamol) on estrus induction in sheep in physiological anestrus. | conference = Reguliatsiia i intensifikatsiia protsessov razmnozheniia sel'skokhoziaistvennykh zhivotnykh: trudy Mezhdunarodnogo simpoziuma, sostoiavshegosia v Sofii, mai 1980 godina/[red. koll.: K. Bratanov (otvet. red.)... i dr.] }}{{cite journal | vauthors = Zhirkov GF | date = 1981 | title = Testing diamol on sheep on a fattening farm. | journal = Biulleten'nauchnykh Rabot-Vsesoiuznyi Nauchno-issledovatel'skii Institut Zhivotnovodstva }}{{cite journal | vauthors = Klinskii I, Zhirkov GF | title = [Use of mepregenol diacetate (Diamol), a gestagen preparation, for estrus synchronization in caracul sheep during mating season] | language = ru | journal = Archiv für Experimentelle Veterinärmedizin | volume = 36 | issue = 1 | pages = 159–162 | date = January 1982 | pmid = 7201304 }} It has been marketed since at least 1981.