Acetomepregenol

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]

Acetomepregenol
Clinical data
Trade namesDiamol
Other namesACM; 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 classProgestogen; Progestin; Progestogen ester
Identifiers
  • [(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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H36O5
Molar mass428.569 g·mol−1
3D model (JSmol)
  • CC1=CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(CC4)OC(=O)C)C
  • InChI=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
  • Key:SDHHPVPFUVQWKY-AVHYYFBHSA-N

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 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]

References