Acetomepregenol
Progestin; Progestogen ester | |
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Acetomepregenol (ACM), also known as mepregenol diacetate and sold under the brand name Diamol, is a
threatened abortion.[3] It has been used in veterinary medicine as well.[8][9][10] It has been marketed since at least 1981.[8][9][10]
Pharmacology
Based on its chemical structure, namely the lack of a C3 ketone, it is probable that acetomepregenol is a prodrug of megestrol acetate (the 3-keto analogue).[11][12]
Chemistry
Acetomepregenol, also known as megestrol 3β,17α-diacetate, as well as 3β-dihydro-6-dehydro-6-methyl-17α-hydroxyprogesterone diacetate or as 3β,17α-diacetoxy-6-methylpregna-4,6-dien-20-one, is a
hydroxyl group with an acetate ester attached at the C3 position instead of a ketone.[3][4][7] A closely related medication is cymegesolate (also known as megestrol 3β-cypionate 17α-acetate), which, in contrast, has not been marketed.[13][14]
References
- PMID 3899717.
- PMID 3116530.
- ^ PMID 2278305.
- ^ S2CID 44235508.
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].
- S2CID 24703856.
- S2CID 35450212.
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].
- ^ S2CID 7159432.
- ^ a b Bratanov K, Bankov N, Doichev S, Pisheva M, Klinskii IU, Zhirkov G (1981). Action of diacetate mepregnol (diamol) on estrus induction in sheep in physiological anestrus. 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.]
- ^ a b Zhirkov GF (1981). "Testing diamol on sheep on a fattening farm". Biulleten'nauchnykh Rabot-Vsesoiuznyi Nauchno-issledovatel'skii Institut Zhivotnovodstva.
- ^ PMID 7201304.
- ISBN 978-0-443-04706-0.
Progestational activity depends on the presence of a 3-keto group in ring A of the steroid skeleton. Most of the progestogens used today do indeed carry such a group in their original molecules. However, the 3-keto group is initially missing in the case of desogestrel and norgestimate. They are prodrugs which undergo metabolic conversion to active 3-keto derivatives in the body.
- S2CID 5612000.
Prodrugs (lack 3-keto): Ethylestrenol, Lynestrenol, Ethynodiol, Allylestrenol, Norgestimate
- S2CID 44858028.
- ISBN 978-3-642-67892-9.