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坎利酮

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坎利酮
Skeletal formula of canrenone
Ball-and-stick model of the canrenone molecule
临床资料
商品名英语Drug nomenclatureContaren, Luvion, Phanurane, Spiroletan
其他名称Aldadiene;[1] SC-9376; RP-11614; 7α-Desthioacetyl-δ6-spironolactone; 6,7-Dehydro-7α-desthioacetylspironolactone; 17-Hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid γ-lactone
AHFS/Drugs.com国际药品名称
药物类别英语Drug class抗盐皮质激素
ATC码
药物动力学数据
血浆蛋白结合率95%
生物半衰期16.5 hours[2]
识别信息
  • 10,13-Dimethylspiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione
CAS号976-71-6  checkY
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.012.322 编辑维基数据链接
化学信息
化学式C22H28O3
摩尔质量340.46 g·mol−1
3D模型(JSmol英语JSmol
  • O=C5\C=C4\C=C/[C@@H]1[C@H](CC[C@]3([C@H]1CC[C@]32OC(=O)CC2)C)[C@@]4(C)CC5
  • InChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1 checkY
  • Key:UJVLDDZCTMKXJK-WNHSNXHDSA-N checkY

坎利酮(英语:Canrenone,商品名有:Contaren、Luvion、Phanurane、Spiroletan等),别名坎利酸内酯烯睾丙内酯。是一种有机化合物,分子式为C22H28O3,属于甾体抗盐皮质激素[3][4],临床上可用作醛固酮拮抗剂治疗水肿心衰高血压、肝腹水等疾病[5],在意大利比利时等国也用作利尿剂[6][7][8][9],同时也是螺内酯活性代谢产物[10][2]。坎利酮可被赭曲霉等微生物发酵作用对11号碳进行羟基化,得到11α-羟基坎利酮[11][5]。坎利酮同时也是螺内酯和依普利酮的原料[12]

坎利酮抗盐皮质激素作用比螺内酯强,但抗雄激素作用要弱于螺内酯[13][14],不过利用其抗雄激素作用可用于治疗女性多毛症英语Hirsutism[15]。作为利尿剂,螺内酯转化成系列代谢产物后,坎利酮贡献了约10-25%的保钾利尿作用英语Potassium-sparing diuretic7α-硫代甲基螺内酯英语7α-Thiomethylspironolactone则主要贡献了约80%[16][17][18]

坎利酸

参考文献

[编辑]
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  2. ^ 2.0 2.1 Gardiner P, Schrode K, Quinlan D, Martin BK, Boreham DR, Rogers MS, et al. Spironolactone metabolism: steady-state serum levels of the sulfur-containing metabolites. Journal of Clinical Pharmacology. April 1989, 29 (4): 342–347. PMID 2723123. S2CID 29457093. doi:10.1002/j.1552-4604.1989.tb03339.x. 
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  6. ^ Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 210–. ISBN 978-1-4757-2085-3. 
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  8. ^ Romanelli RG, Gentilini P. Cross reactivity due to positive canrenone interference. Gut. May 2004, 53 (5): 772–773. PMC 1774040可免费查阅. PMID 15082604. 
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  11. ^ 刘晓,刘逸寒,别松涛,等. 赭曲霉的高密度培养对坎利酮转化的影响. 生物技术. 2012, 21 (5): 82-87. doi:10.3969/j.issn.1004-311X.2011.05.134. 
  12. ^ 张映华,熊志刚,邱国福,等. 依普利酮中间体坎利酮的合成工艺改进. 中国药物化学杂志. 2005, 15 (4): 241-243. doi:10.3969/j.issn.1005-0108.2005.04.013. 
  13. ^ Coelingh Benni H, Vemer H. Chronic Hyperandrogenic Anovulation. CRC Press. 15 December 1990: 152–. ISBN 978-1-85070-322-8. 
  14. ^ Seldin DW, Giebisch GH. Diuretic Agents: Clinical Physiology and Pharmacology. Academic Press. 23 September 1997: 630–. ISBN 978-0-08-053046-8. 
  15. ^ Sobbrio GA, Granata A, Panacea A, Trimarchi F. Effectiveness of short term canrenone treatment in idiopathic hirsutism. Minerva Endocrinologica. 1989, 14 (2): 105–108. PMID 2761494. 
  16. ^ Maron BA, Leopold JA. Mineralocorticoid receptor antagonists and endothelial function. Current Opinion in Investigational Drugs. September 2008, 9 (9): 963–969. PMC 2967484可免费查阅. PMID 18729003. 
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  18. ^ Agusti G, Bourgeois S, Cartiser N, Fessi H, Le Borgne M, Lomberget T. A safe and practical method for the preparation of 7α-thioether and thioester derivatives of spironolactone. Steroids. January 2013, 78 (1): 102–107. PMID 23063964. S2CID 8992318. doi:10.1016/j.steroids.2012.09.005.