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達那唑

維基百科,自由的百科全書
達那唑
臨床資料
商品名英語Drug nomenclatureDanatrol, Danocrine, Danol, Danoval, others
其他名稱WIN-17757; 2,3-Isoxazolethisterone; 2,3-Isoxazol-17α-ethynyltestosterone; 17α-Ethynyl-17β-hydroxyandrost-4-en-[2,3-d]isoxazole
AHFS/Drugs.comMonograph
MedlinePlusa682599
懷孕分級
  • : D
給藥途徑口服給藥
藥物類別英語Drug class雄激素同化類固醇黃體製劑孕激素抗促性腺激素英語Antigonadotropin固醇類合成抑制劑英語Steroidogenesis inhibitor抗動情素藥物英語Antiestrogen
ATC碼
法律規範狀態
法律規範
藥物動力學數據
生物利用度Saturable with dosage, higher with food intake[1]
血漿蛋白結合率會與白蛋白英語human serum albuminSHBG, CBG結合[2][3][4]
藥物代謝肝臟CYP3A4[8][5][9][1][6]
代謝產物2-OHM-Ethisterone[5]
Ethisterone[6][7]
生物半衰期Acute: 3–10 hours[8][1]
Chronic: 24–26 hours[8]
排泄途徑尿糞便[8][1]
識別資訊
  • (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號17230-88-5  checkY
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard英語CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.037.503 編輯維基數據鏈接
化學資訊
化學式C22H27NO2
摩爾質量337.463 g/mol
3D模型(JSmol英語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

達那唑(Danazol)為一種用於治療子宮內膜異位症乳腺小葉增生遺傳性血管性水腫英語hereditary angioedema及其他疾病的藥物[8][1][10][11][12],主要經口服給藥[1]

達那唑具有雄性化副作用,使其用途大受限制。常見不良反應包含痤瘡多毛症,以及聲音變低沉[1][13]。達那唑的作用機轉複雜,同時具有弱雄激素、弱同化類固醇、弱孕激素,弱抗促性腺激素英語Antigonadotropin、弱固醇類合成抑制劑英語steroidogenesis inhibitor,以及功能性抗動情素藥物英語Antiestrogen[4][9][14][9][14][15]

達那唑發現於1963年,並於1971年應用於醫學[9][16][17][18]。隨著副作用更少的性腺激素釋放素類似物英語gonadotropin-releasing hormone analogue應用逐漸廣泛,達那唑在治療子宮內膜異位症的角色已被前者所取代[3]

參考文獻

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  1. ^ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 存档副本 (PDF). [2019-10-09]. (原始內容存檔 (PDF)於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. (原始內容存檔於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. (原始內容存檔於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. (原始內容存檔於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. (原始內容存檔於2020-01-10). 
  8. ^ 8.0 8.1 8.2 8.3 8.4 Brayfield, A (編). Danazol. Martindale: The Complete Drug Reference. Pharmaceutical Press. 30 October 2013 [1 April 2014]. (原始內容存檔於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. (原始內容存檔於2020-01-10).  引用錯誤:帶有name屬性「JonesRock2015」的<ref>標籤用不同內容定義了多次
  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. (原始內容存檔於2020-01-10). 
  12. ^ I.K. Morton; Judith M. Hall. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012: 91–. ISBN 978-94-011-4439-1. 
  13. ^ Selak V, Farquhar C, Prentice A, Singla A. Farquhar C , 編. 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. (原始內容存檔於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. (原始內容存檔於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]. (原始內容存檔於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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