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表雄酮

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表雄酮
Skeletal formula of epiandrosterone
Ball-and-stick model of the epiandrosterone molecule
臨床資料
ATC碼
  • 未分配
識別資訊
  • (3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
    OR
    (1S,2S,5S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-one
CAS號481-29-8  checkY
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard英語CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.006.877 編輯維基數據鏈接
化學資訊
化學式C19H30O2
摩爾質量290.440 g/mol
3D模型(JSmol英語JSmol
  • O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@@H](O)CC[C@]34C)C
  • InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1 checkY
  • Key:QGXBDMJGAMFCBF-LUJOEAJASA-N checkY

表雄酮(英語:Epiandrosterone)或稱為異雄酮(英語:isoandrosterone[1][2]是一種甾體激素,擁有較弱的雄激素活性,是睾酮雙氫睾酮(DHT)的代謝產物,在1931年由阿道夫·布特南特庫爾特·切爾寧首次分離。他們蒸餾了17000升的男性尿液,從中得到50毫克的雄酮結晶(很可能是混合了的α/β異構體),並發現其和雌酮有着相似的化學結構。

大部分哺乳動物包括豬都能合成表雄酮[3],在體內可由5α還原酶催化腎上腺激素DHEA而來[4][5][6][7],另外也可由3β-雄烷二醇17β-羥基類固醇脫氫酶催化或雄烷二酮3β-羥基類固醇脫氫酶催化而來。

參見

參考文獻

  1. ^ Samuel H. Yalkowsky; Yan He; Parijat Jain. Handbook of Aqueous Solubility Data, Second Edition. CRC Press. 19 April 2016: 1209–. ISBN 978-1-4398-0246-5. 
  2. ^ Natural Products. Krishna Prakashan Media. 2006: 298–. ISBN 978-81-87224-85-3. 
  3. ^ Raeside JI, Renaud RL, Marshall DE. Identification of 5 alpha-androstane-3 beta,17 beta-diol and 3 beta-hydroxy-5 alpha-androstan-17-one sulfates as quantitatively significant secretory products of porcine Leydig cells and their presence in testicular venous blood. J Steroid Biochem Mol Biol. 42(1):113-20, 1992
  4. ^ Callies F, Arlt W, Siekmann L, Hübler D, Bidlingmaier F, Allolio B. Influence of oral dehydroepiandrosterone (DHEA) on urinary steroid metabolites in males and females. Steroids. 65(2):98-102, 2000
  5. ^ Labrie F, Cusan L, Gomez JL, Martel C, Bérubé R, Bélanger P, Chaussade V, Deloche C, Leclaire J. Changes in serum DHEA and eleven of its metabolites during 12-month percutaneous administration of DHEA. J Steroid Biochem Mol Biol. 2008 May;110(1-2):1-9
  6. ^ Daniël Henri van de Kerkhof. Steroid profiling in doping analysis. [S.l.] : [s.n.], 2001 - Tekst. - Proefschrift Universiteit Utrecht
  7. ^ Acacio BD, Stanczyk FZ, Mullin P, Saadat P, Jafarian N, Sokol RZ. Pharmacokinetics of dehydroepiandrosterone and its metabolites after long-term daily oral administration to healthy young men. Fertil Steril. Mar;81(3):595-604, 2004