17α-메틸프로게스테론

17α-Methylprogesterone
17α-메틸프로게스테론
임상자료
기타이름17α-MP; 17α-Methylpregn-4-ene-3,20-dione
약품반프로게스틴; 프로게스토겐
식별자
  • (8R,9S,10R,13S,14S,17S)-17-acetyl-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS 번호
펍켐 CID
켐스파이더
유니아이
CompTox 대시보드 (EPA)
화학물질 및 물리적 데이터
공식C22H32O2
어금니 질량328.496 g·mol−1
3D 모델(Jsmol)
  • CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C
  • InChI=1S/C22H32O2/c1-14(23)21(3)11-9-19-17-6-5-15-13-16(24)7-10-20(15,2)18(17)8-12-22(19,21)4/h13,17-19H,5-12H2,1-4H3/t17-,18+,19+,20+,21-,22+/m1/s1
  • Key:UFIQEZHBGZCWRS-QZKGNRECSA-N

17α-Methylprogesterone (17α-MP) 또는 17α-Methylpregn-4-ene-3,20-dione는 1949년에 합성되고 특성화되었지만 시판되지 않은 프로게스테론과 관련된 스테로이드성 프로게스틴입니다.[1] 17α-MP는 ethisterone(1938)[2] 및 19-nor progesterone(1951)과 함께 프로게스테론의 가장 초기 유도체 중 하나였습니다. 프로게스테론 및 17α-하이드록시프로게스테론 및 19-노르프로게스테론과 같은 유도체와 유사하게, 17α-MP는 낮은(무작위적이지는 않지만) 경구 생체이용률을 갖는 [3]것으로 밝혀졌지만, 다른 경로(예: 피하 또는 질)를 통해 투여될 때 프로게스테론에 비해 개선된 프로게스테론 활성을 보였습니다.[4][5][6] 17α-MP는 프로게스토겐으로서의 활성 외에도 일부 항글루코코르티코이드 활성을 갖는 것으로 밝혀졌습니다.[7]

프로게스테론에 비해 17α-MP의 2배 향상된 효능의 관찰은 프로게스테론의 17α-치환 유도체에 대한 새로운 관심으로 이어졌습니다.[5] 그 후 1953년에 하이드록시프로게스테론 아세테이트와 하이드록시프로게스테론 카프로에이트를 합성하여 각각 1956년과 1957년에 도입하였고 1957년에 메드록시프로게스테론 아세테이트를 발견하여 1959년에 도입하였습니다.[5] 또한, 17α-MP 자체는 의료용으로 도입된 적이 없지만, 메드로게스톤(1966) 및 19-노르로게스테론 유도체(1974), 프로메게스톤(1983) 및 트리메게스톤(2001)을 포함한 화합물의 프로게스토겐 유도체가 시판되었습니다.[8]

화학

참고 항목: 프로게스토겐 목록

참고 항목

참고문헌

  1. ^ 플래트너, 플래트너, 호이저, 피. 허치그. "* UBER 스테로이드 및 성적 호르몬. 159. 다이 합성 폰 17-메틸-프로게스테론." 헬베티카 키미카 ACTA 32.1 (1949): 270-275.
  2. ^ Zderic JA (1963). "Progestational hormones". Comprehensive Biochemistry. Elsevier. pp. 166–196.
  3. ^ Luciano Martini; Antonio Pecile (1965). Hormonal steroids: biochemistry, pharmacology and therapeutics; proceedings. Academic Press. p. 95. ISBN 9780124753020. Progesterone is devoid of appreciable oral activity, but, particularly at positions 6 and 17, substituents of metabolic importance are known to impart oral activity to the molecule (Fieser and Fieser, 1959). We wish to report the preparation of 6- and 21 -substituted 17- methylprogesterones, a class of substances which we synthesized after the observation that 17-methylprogesterone (Plattner et al., 1949), contrary to previous reports (Engel, 1951, 1960), was not devoid of oral activity (cf. Table I).
  4. ^ Ralph I. Dorfman (3 February 2016). Bioassay. Elsevier. pp. 260–. ISBN 978-1-4832-7276-4. 17-Methylprogesterone is effective subcutaneously or intravaginally, but is ineffective orally.
  5. ^ a b c Norman Applezweig (1962). Steroid Drugs. Blakiston Division, McGraw-Hill. pp. 101–102. In 1950, 17a-methyl-progesterone was shown to have twice the activity of progesterone. This led to a renewed interest in 17-substituted derivatives. [...] Junkmann of Schering, AG., however, was able to show that long chain esters of 17a-hydroxyprogesterones such as the 17a-caproate produced powerful long-acting progestational effect. This compound is marketed in the United States as Delalutin by Squibb, and has been heavily used for the treatment of habitual abortion. Subsequently, a series of events led to the exploitation of 17a-hydroxyprogesterone derivatives as highly effective and orally active progestogens. Groups at Upjohn, Merck & Co., and Syntex independently found means of readily acetylating the 17-hydroxy group. Later, Upjohn announced it found that 17a-acetoxyprogesterone was orally active in humans and subsequently marketed this compound under the name of Prodox. The idea that progesterone could be protected by substitution against metabolic destruction was not exclusive to one group of investigators. [...] Upjohn later brought out the 6a-methyl-17a-acetoxyprogesterone under the name of Provera. This is ten to twenty-five times as active as ethisterone by oral route.
  6. ^ TULLNER WW, HERTZ R (1953). "High progestational activity of 19-norprogesterone". Endocrinology. 52 (3): 359–61. doi:10.1210/endo-52-3-359. PMID 13033848. 17-methylprogesterone A has twice the activity of progesterone using the Corner-Allen assay method (Heuser et al., 1950).
  7. ^ Duncan MR, Duncan GR (1979). "An in vivo study of the action of antiglucocorticoids on thymus weight ratio, antibody titre and the adrenal-pituitary-hypothalamus axis". Journal of Steroid Biochemistry. 10 (3): 245–59. doi:10.1016/0022-4731(79)90250-4. PMID 222960.
  8. ^ Revesz C, Chappel CI (1966). "Biological activity of medrogestone: a new orally active progestin". Journal of Reproduction and Fertility. 12 (3): 473–87. doi:10.1530/jrf.0.0120473. PMID 4288903. The desirability of an orally active progestin which would be free from these objectionable properties led to the synthesis of a series of derivatives of 17-methylprogesterone (Deghenghi & Gaudry, 1961; Deghenghi, Revesz & Gaudry, 1963) and their testing as progestational agents. The biological activity of 6-methyl-6-dehydro-17-methylprogesterone, which appeared to be the most promising member of this series, [...]