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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 |
Identifiers | |
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CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C26H36O5 |
Molar mass | 428.569 g·mol−1 |
3D model ( JSmol) | |
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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. [1] [2] [3] [4] [5] [6] [7] It has also been studied in the treatment of 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]
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]
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 synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone. [3] [4] [7] It is very close to megestrol acetate (6-dehydro-6-methyl-17α-acetoxyprogesterone) in structure, except that there 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]
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
![]() | |
Clinical data | |
---|---|
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 |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C26H36O5 |
Molar mass | 428.569 g·mol−1 |
3D model ( JSmol) | |
| |
|
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. [1] [2] [3] [4] [5] [6] [7] It has also been studied in the treatment of 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]
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]
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 synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone. [3] [4] [7] It is very close to megestrol acetate (6-dehydro-6-methyl-17α-acetoxyprogesterone) in structure, except that there 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]
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