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达那唑

维基百科,自由的百科全书
达那唑
临床资料
商品名英语Drug nomenclatureDanatrol, Danocrine, Danol, Danoval, others
其他名称WIN-17757; 2,3-Isoxazolethisterone; 2,3-Isoxazol-17α-ethynyltestosterone; 17α-Ethynyl-17β-hydroxyandrost-4-en-[2,3-d]isoxazole
AHFS/Drugs.comMonograph
MedlinePlusa682599
怀孕分级
  • : D
给药途径口服给药
药物类别英语Drug class雄激素同化类固醇黄体制剂孕激素抗促性腺激素英语Antigonadotropin固醇类合成抑制剂英语Steroidogenesis inhibitor抗动情素药物英语Antiestrogen
ATC码
法律规范状态
法律规范
药物动力学数据
生物利用度Saturable with dosage, higher with food intake[1]
血浆蛋白结合率会与白蛋白英语human serum albuminSHBG, CBG结合[2][3][4]
药物代谢肝脏CYP3A4[8][5][9][1][6]
代谢产物2-OHM-Ethisterone[5]
Ethisterone[6][7]
生物半衰期Acute: 3–10 hours[8][1]
Chronic: 24–26 hours[8]
排泄途径尿粪便[8][1]
识别信息
  • (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol
CAS号17230-88-5  checkY
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.037.503 编辑维基数据链接
化学信息
化学式C22H27NO2
摩尔质量337.463 g/mol
3D模型(JSmol英语JSmol
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC5=C(C[C@]34C)C=NO5
  • InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1 checkY
  • Key:POZRVZJJTULAOH-LHZXLZLDSA-N checkY

达那唑(Danazol)为一种用于治疗子宫内膜异位症乳腺小叶增生遗传性血管性水肿英语hereditary angioedema及其他疾病的药物[8][1][10][11][12],主要经口服给药[1]

达那唑具有雄性化副作用,使其用途大受限制。常见不良反应包含痤疮多毛症,以及声音变低沉[1][13]。达那唑的作用机转复杂,同时具有弱雄激素、弱同化类固醇、弱孕激素,弱抗促性腺激素英语Antigonadotropin、弱固醇类合成抑制剂英语steroidogenesis inhibitor,以及功能性抗动情素药物英语Antiestrogen[4][9][14][9][14][15]

达那唑发现于1963年,并于1971年应用于医学[9][16][17][18]。随著副作用更少的性腺激素释放素类似物英语gonadotropin-releasing hormone analogue应用逐渐广泛,达那唑在治疗子宫内膜异位症的角色已被前者所取代[3]

参考文献

  1. ^ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 存档副本 (PDF). [2019-10-09]. (原始内容存档 (PDF)于2021-04-02). 
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  3. ^ 3.0 3.1 Eberhard Nieschlag; Hermann M. Behre; Susan Nieschlag. Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. 13 January 2010: 426–428. ISBN 978-3-540-78355-8. 
  4. ^ 4.0 4.1 Eric J. Thomas; John Rock. Modern Approaches to Endometriosis. Springer Science & Business Media. 6 December 2012: 239–256 [2019-10-09]. ISBN 978-94-011-3864-2. (原始内容存档于2020-01-10). 
  5. ^ 5.0 5.1 Thomas L. Lemke; David A. Williams. Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. 24 January 2012: 1361– [2019-10-09]. ISBN 978-1-60913-345-0. (原始内容存档于2020-01-10). 
  6. ^ 6.0 6.1 Florencio Zaragoza Dörwald. Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. 4 February 2013: 485– [2019-10-09]. ISBN 978-3-527-64565-7. (原始内容存档于2020-01-09). 
  7. ^ Robert J. Kurman. Blaustein's Pathology of the Female Genital Tract. Springer Science & Business Media. 17 April 2013: 390– [2019-10-09]. ISBN 978-1-4757-3889-6. (原始内容存档于2020-01-10). 
  8. ^ 8.0 8.1 8.2 8.3 8.4 Brayfield, A (编). Danazol. Martindale: The Complete Drug Reference. Pharmaceutical Press. 30 October 2013 [1 April 2014]. (原始内容存档于2021-08-28). 
  9. ^ 9.0 9.1 9.2 9.3 Howard W. Jones; John A. Rock. Te Linde's Operative Gynecology. Wolters Kluwer Health. 10 July 2015: 1327–1330 [2019-10-09]. ISBN 978-1-4963-1521-2. (原始内容存档于2020-01-10).  引用错误:带有name属性“JonesRock2015”的<ref>标签用不同内容定义了多次
  10. ^ J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 345–. ISBN 978-1-4757-2085-3. 
  11. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000: 293– [2019-10-09]. ISBN 978-3-88763-075-1. (原始内容存档于2020-01-10). 
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  13. ^ Selak V, Farquhar C, Prentice A, Singla A. Farquhar C , 编. Danazol for pelvic pain associated with endometriosis. Cochrane Database of Systematic Reviews. 2007, (4): CD000068. PMID 17943735. doi:10.1002/14651858.CD000068.pub2. 
  14. ^ 14.0 14.1 Aurel Lupulescu. Hormones and Vitamins in Cancer Treatment. CRC Press. 24 October 1990: 103– [2019-10-09]. ISBN 978-0-8493-5973-6. (原始内容存档于2020-01-10). 
  15. ^ Albert Altchek; Liane Deligdisch; Nathan Kase. Diagnosis and Management of Ovarian Disorders. Academic Press. 4 September 2003: 376– [2019-10-09]. ISBN 978-0-08-049451-7. (原始内容存档于2020-01-09). 
  16. ^ G.P. Ellis and G.B. Ellis, doi:10.1016/S0079-6468(08)70187-5 (1979),  pp. 126, note 158, 130, notes 1513, 2369, citing doi:10.1021/jm00299a034
  17. ^ Alan N. Elias; Grant Gwinup. Hirsutism. Praeger. 1 January 1983: 70 [2019-10-09]. (原始内容存档于2017-03-28). 
  18. ^ Dmowski WP, Scholer HF, Mahesh VB, Greenblatt RB. Danazol--a synthetic steroid derivative with interesting physiologic properties. Fertil. Steril. 1971, 22 (1): 9–18. PMID 5538758. doi:10.1016/S0015-0282(16)37981-X. 

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