아세토메프레게놀

Acetomepregenol
아세토메프레게놀
Acetomepregenol.svg
임상자료
상명디아몰
기타 이름ACM; 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
마약류프로게스테겐; 프로게스틴; 프로게스테겐 에스테르
식별자
  • [(3S,8R,9S,10R,13S,14S,17R)-17-아세틸-17-아세틸-6,10,13-트리메틸-1,2,3,8,11,12,14,15,16-데카하이드로사이클로펜타[a]피난트렌트-3-yl]아세트산염
CAS 번호
펍켐 CID
켐스파이더
유니
CompTox 대시보드 (EPA)
화학 및 물리적 데이터
공식C26H36O5
어금질량428.569 g·198−1
3D 모델(JSmol)
  • CC1=CC2C(CCC3(C2CC3)(=O)C)OC(=O)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
  • 키:SDHPVPFUVFUVQWKY-AVHYFBHSA-N

아세트메프레게놀(ACM)은 러시아에서 산부인과 질환 치료와 에스트로겐과 결합한 산아제한 방법으로 사용되는 프로게스틴 약품이다.[1][2][3][4][5][6][7] 그것은 또한 낙태에 대한 위협적인 치료에서도 연구되어 왔다.[3] 그것은 수의학에서도 사용되었다.[8][9][10] 그것은 적어도 1981년부터 판매되어 왔다.[8][9][10]

약리학

화학적 구조, 즉 C3케톤이 없는 것으로 보아 아세토메프레게놀은 메게스트롤 아세테이트(3케토 아날로그)의 원약일 가능성이 높다.[11][12]

화학

참고 항목: 프로게스겐 에스테르 목록, 프로게스겐 에스테르 목록

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] 케톤 대신 C3 위치에 아세테이트 에스테르가 부착된 히드록실 그룹이 있다는 점을 제외하면 구조상 메게스트롤 아세테이트(6-드하이드로-6-메틸-17α-아세톡시프로제스테론)에 매우 가깝다.[3][4][7] 밀접하게 관련된 약물로는 시메게솔레이트(메게스트롤 3β-시피오네이트 17α-아세트산이라고도 한다)가 있는데, 이와는 대조적으로 시판되지 않았다.[13][14]

참조

  1. ^ Korkhov VV (1985). "[Current trends in the development of oral contraception]". Farmakologiia I Toksikologiia (in Russian). 48 (4): 119–22. PMID 3899717.
  2. ^ 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.
  3. ^ a b c d 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.
  4. ^ a b c 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. 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 [4].
  5. ^ 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. S2CID 24703856.
  6. ^ 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. 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 [1, 2]. In clinics, drugs of this group are represented by acetomepregenol (AMP), medroxyprogesterone acetate (MPA), levonorgestrel, progesterone, didrogesterone, etc. [1].
  7. ^ a b c 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. S2CID 7159432.
  8. ^ a b 브라타노프, K, 뱅코프, N, 도이체프, S, 피셰바, M, 클린스키, I. U., & 지르코프, G. (1981) 생리적 마취에서 양의 에스트러스 유도에 대한 디아세트산 메프레놀(diamol)의 작용. 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.].
  9. ^ a b 지르코프, G. F. (1981) 살찌는 농장에서 양에게 직경을 테스트한다. Biulleten'nauchnovodstva.vsoeuznyi nauchni nauchni-isledovatel'ski 연구소.
  10. ^ a b 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.
  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". J. Steroid Biochem. Mol. Biol. 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 Obstet Gynecol Scand Suppl. 105: 51–60. doi:10.3109/00016348209155319. PMID 6952745. S2CID 44858028.
  14. ^ Yang, Yi-chien; Gu, Xi-gen; Li, Shu-xiang (1982). Proteins and Steroids in Early Pregnancy. pp. 335–342. doi:10.1007/978-3-642-67890-5_22. ISBN 978-3-642-67892-9.