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| Clinical data | |
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| Trade names | Diamol |
| Other names | 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 |
| Drug class | Progestogen;Progestin;Progestogen ester |
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| CAS Number | |
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| Chemical and physical data | |
| Formula | C26H36O5 |
| Molar mass | 428.569 g·mol−1 |
| 3D model (JSmol) | |
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Acetomepregenol (ACM), also known asmepregenol diacetate and sold under the brand nameDiamol, is aprogestin medication which is used inRussia for the treatment ofgynecological conditions and as a method ofbirth control in combination with anestrogen.[1][2][3][4][5][6][7] It has also been studied in the treatment ofthreatened abortion.[3] It has been used inveterinary medicine as well.[8][9][10] It has been marketed since at least 1981.[8][9][10]
Based on itschemical structure, specifically the lack of a C3ketone, it is probable that acetomepregenol is aprodrug ofmegestrol acetate (the 3-ketoanalogue).[11][12]
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 asyntheticpregnanesteroid and aderivative ofprogesterone and17α-hydroxyprogesterone.[3][4][7] It is very close tomegestrol acetate (6-dehydro-6-methyl-17α-acetoxyprogesterone) instructure, except that there is ahydroxyl group with anacetateester attached at the C3 position instead of aketone.[3][4][7] A closely related medication iscymegesolate (also known as megestrol 3β-cypionate 17α-acetate), which, in contrast, has not been marketed.[13][14]
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].
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].
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.
Prodrugs (lack 3-keto): Ethylestrenol, Lynestrenol, Ethynodiol, Allylestrenol, Norgestimate
