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Acetomepregenol

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Chemical compound Pharmaceutical compound
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
IUPAC name
  • phenanthren-3-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H36O5
Molar mass428.569 g·mol
3D model (JSmol)
SMILES
  • CC1=CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(CC4)OC(=O)C)C
InChI
  • 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

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.

Pharmacology

Based on its chemical structure, specifically the lack of a C3 ketone, it is probable that acetomepregenol is a prodrug of megestrol acetate (the 3-keto analogue).

Chemistry

See also: List of progestogens, Progestogen ester, and List of progestogen esters

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-acetate), which, in contrast, has not been marketed.

See also

References

  1. Korkhov VV (1985). "". Farmakologiia i Toksikologiia (in Russian). 48 (4): 119–122. PMID 3899717.
  2. Nikitina GV, Savchenko ON, Stepanov MG (1987). "". Problemy Endokrinologii (in Russian). 33 (3): 60–63. PMID 3116530.
  3. ^ Sidel'nikova VM, Demidova EM, Borisova I, Dondukova TM, Absava GI, Korkhov VV (September 1990). "". Akusherstvo I Ginekologiia (in Russian) (9): 37–40. PMID 2278305.
  4. ^ Grinenko GS, Popova EV, Korkhov VV, Lesik EA, Petrosyan MA, Topil'skaya NI (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. 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 .
  5. Mashkovskii MD (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. S2CID 24703856.
  6. Sergeev PV, Rzheznikov VM, Korkhov VV, Grinenko GS, Semeikin AV, Mayatskaya EE, et al. (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. 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 . In clinics, drugs of this group are represented by acetomepregenol (AMP), medroxyprogesterone acetate (MPA), levonorgestrel, progesterone, didrogesterone, etc. .
  7. ^ Zeinalov OA, Yaderets VV, Stytsenko TS, Petrosyan MA, Andryushina VA (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. S2CID 7159432.
  8. ^ 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/
  9. ^ Zhirkov GF (1981). "Testing diamol on sheep on a fattening farm". Biulleten'nauchnykh Rabot-Vsesoiuznyi Nauchno-issledovatel'skii Institut Zhivotnovodstva.
  10. ^ Klinskii I, Zhirkov GF (January 1982). "". Archiv Fur Experimentelle Veterinarmedizin (in Russian). 36 (1): 159–162. PMID 7201304.
  11. 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.
  12. 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". The Journal of Steroid Biochemistry and Molecular Biology. 110 (1–2): 39–47. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441. S2CID 5612000. Prodrugs (lack 3-keto): Ethylestrenol, Lynestrenol, Ethynodiol, Allylestrenol, Norgestimate
  13. De-Wei Z (1982). "Research activities in the field of oral contraceptives in the People's Republic of China". Acta Obstetricia et Gynecologica Scandinavica. Supplement. 105: 51–60. doi:10.3109/00016348209155319. PMID 6952745. S2CID 44858028.
  14. Yang YC, Gu XG, Li SX (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". Proteins and Steroids in Early Pregnancy. pp. 335–342. doi:10.1007/978-3-642-67890-5_22. ISBN 978-3-642-67892-9.
Progestogens and antiprogestogens
Progestogens
(and progestins)
PRTooltip Progesterone receptor agonists
Antiprogestogens
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Androgens and antiandrogens
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List of progestogens
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PRTooltip Progesterone receptor
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mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
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Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
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