|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|
|Drug class||Progestin; Progestogen; Progestogen ester|
|Chemical and physical data|
|Molar mass||428.561 g/mol|
|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. It has also been studied in the treatment of threatened abortion. It has been used in veterinary medicine as well. It has been marketed since at least 1981.
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. 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. A closely related medication is cymegesolate (also known as megestrol 3β-cypionate 17α-diacetate), which, in contrast, has not been marketed.
- Korkhov VV (1985). "[Current trends in the development of oral contraception]". Farmakologiia I Toksikologiia (in Russian). 48 (4): 119–22. PMID 3899717.
- Nikitina GV, Savchenko ON, Stepanov MG (1987). "[Hormonal properties of new 17 alpha-hydroxyprogesterone derivatives]". Problemy ĖNdokrinologii (in Russian). 33 (3): 60–3. PMID 3116530.
- Sidel'nikova VM, Demidova EM, Borisova IuF, Dondukova TM, Absava GI, Korkhov VV (1990). "[The use of acetomepegrenol in the therapy of threatened abortion]". Akusherstvo I Ginekologii︠a︡ (in Russian) (9): 37–40. PMID 2278305.
- Grinenko, G. S.; Popova, E. V.; Korkhov, V. V.; Lesik, E. A.; Petrosyan, M. A.; Topil'skaya, N. I. (March 2000). "Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal. 34 (3): 113–114. doi:10.1007/BF02524577. ISSN 1573-9031.
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 .
- Mashkovskii, M. D. (December 2000). "Eightieth Anniversary of the Drug Chemistry Center/All-Russian Pharmaceutical Chemistry Scientific Research Institute". Pharmaceutical Chemistry Journal. 34 (12): 677–680. doi:10.1023/A:1010416205068. ISSN 1573-9031.
- Sergeev, P. V.; Rzheznikov, V. M.; Korkhov, V. V.; Grinenko, G. S.; Semeikin, A. V.; Mayatskaya, E. E.; Samoilikov, R. V.; Shimanovskii, N. L. (July 2005). "Investigation of the Gestagen Activity of 17α-acetoxy-3β-butanoyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal. 39 (7): 358–360. doi:10.1007/s11094-005-0154-4. ISSN 1573-9031.
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. .
- Zeinalov, O. A.; Yaderets, V. V.; Stytsenko, T. S.; Petrosyan, M. A.; Andryushina, V. A. (July 2012). "Synthesis and biological activity of synthetic 17α-hydroxyprogesterone derivatives". Pharmaceutical Chemistry Journal. 46 (4): 203–206. doi:10.1007/s11094-012-0761-9. ISSN 1573-9031.
- Bratanov, K., Bankov, N., Doichev, S., Pisheva, M., Klinskii, I. U., & 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.].
- Zhirkov, G. F. (1981). Testing diamol on sheep on a fattening farm. Biulleten'nauchnykh rabot-Vsesoiuznyi nauchno-issledovatel'skii institut zhivotnovodstva.
- Klinskii ID, Zhirkov GF (1982). "[Use of mepregenol diacetate (Diamol), a gestagen preparation, for estrus synchronization in caracul sheep during mating season]". Arch Exp Veterinarmed (in Russian). 36 (1): 159–62. PMID 7201304.
- Ian S. Fraser (1998). Estrogens and Progestogens in Clinical Practice. Churchill Livingstone. p. 281. 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.
- McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (May 2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1-2): 39–47. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441.
Prodrugs (lack 3-keto): Ethylestrenol, Lynestrenol, Ethynodiol, Allylestrenol, Norgestimate
- De-Wei Z (1982). "Research activities in the field of oral contraceptives in the People's Republic of China". Acta Obstet Gynecol Scand Suppl. 105: 51–60. PMID 6952745.
- Yang, Yi-chien; Gu, Xi-gen; Li, Shu-xiang (1982). "Antifertility Effect of a Long-Acting Progestin (3-Cyclopentyl Propionate of Megestrol Acetate): Prematurity of the Endometrium and Accompanying Changes of Uteroglobin and Progesterone in Uterine Fluid": 335–342. doi:10.1007/978-3-642-67890-5_22.