表雄酮

表雄酮
临床资料
ATC码	未分配;
识别信息
	IUPAC命名法 (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号	481-29-8
PubChem CID	441302;
ChemSpider	390065 ;
UNII	8TR252Z538;
ChEBI	CHEBI:541975 ;
ChEMBL	ChEMBL272195 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID20289698 ;
ECHA InfoCard	100.006.877
化学信息
化学式	C19H30O2
摩尔质量	290.440 g/mol
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES 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 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 ; Key:QGXBDMJGAMFCBF-LUJOEAJASA-N ;

表雄酮（英语：Epiandrosterone）或称为异雄酮（英语：isoandrosterone）^[1]^[2]是一种甾体激素，拥有较弱的雄激素活性，是睾酮和双氢睾酮（DHT）的代谢产物，在1931年由阿道夫·布特南特和库尔特·切尔宁首次分离。他们蒸馏了17000升的男性尿液，从中得到50毫克的雄酮结晶（很可能是混合了的α/β异构体），并发现其和雌酮有着相似的化学结构。

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大部分哺乳动物包括猪都能合成表雄酮^[3]，在体内可由5α还原酶催化肾上腺激素DHEA而来^[4]^[5]^[6]^[7]，另外也可由3β-雄烷二醇经17β-羟基类固醇脱氢酶催化或雄烷二酮经3β-羟基类固醇脱氢酶催化而来。

[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

[YalkowskyHe2016-1] [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.

[KrishnaPrakashanMedia2006-2] [2]
Natural Products. Krishna Prakashan Media. 2006: 298–. ISBN 978-81-87224-85-3.

[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] [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] [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] [6]
Daniël Henri van de Kerkhof. Steroid profiling in doping analysis. [S.l.] : [s.n.], 2001 - Tekst. - Proefschrift Universiteit Utrecht

[7] [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

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[2]

[3]

[4]

[5]

[6]

[7]

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表雄酮

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参见

参考文献

临床资料


ATC码	未分配
识别信息
IUPAC命名法 (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[8.7.0.0^2,7.0^11,15]heptadecan-14-one
CAS号	481-29-8 ^Y
PubChem CID	441302
ChemSpider	390065^Y
UNII	8TR252Z538
ChEBI	CHEBI:541975^Y
ChEMBL	ChEMBL272195^Y
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID20289698
ECHA InfoCard	100.006.877
化学信息
化学式	C₁₉H₃₀O₂
摩尔质量	290.440 g/mol
3D模型（JSmol（英语：JSmol））	交互式图像
SMILES 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 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^Y Key:QGXBDMJGAMFCBF-LUJOEAJASA-N^Y