達那唑

達那唑
臨床資料
商品名（英语：Drug nomenclature）	Danatrol, 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.com	Monograph
MedlinePlus	a682599
懷孕分級	澳: D ; ;
给药途径	口服给药
藥物類別（英语：Drug class）	雄激素、同化類固醇、黄体制剂、孕激素、抗促性腺激素（英语：Antigonadotropin）、固醇類合成抑制劑（英语：Steroidogenesis inhibitor）、抗動情素藥物（英语：Antiestrogen）
ATC碼	G03XA01 (WHO) ;
法律規範狀態
法律規範	澳：限医生处方（S4）; 加：处方药（℞-only）; 英：处方药（℞-only） (POM); 美：处方药（℞-only）;
藥物動力學數據
生物利用度	Saturable with dosage, higher with food intake
血漿蛋白結合率	會與白蛋白（英语：human serum albumin）、SHBG, CBG結合
药物代谢	肝臟（CYP3A4）
代謝產物	• 2-OHM-Ethisterone; • Ethisterone
生物半衰期	Acute: 3–10 hours; Chronic: 24–26 hours
排泄途徑	尿、糞便
识别信息
	IUPAC命名法 (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
PubChem CID	28417;
IUPHAR/BPS	6942;
DrugBank	DB01406 ;
ChemSpider	26436 ;
UNII	N29QWW3BUO;
KEGG	D00289 ;
ChEBI	CHEBI:4315 ;
ChEMBL	ChEMBL1479 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID2022880 ;
ECHA InfoCard	100.037.503
化学信息
化学式	C22H27NO2
摩尔质量	337.463 g/mol
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES 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 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 ; Key:POZRVZJJTULAOH-LHZXLZLDSA-N ;

達那唑（Danazol）為一種用於治療子宮內膜異位症、乳腺小叶增生、遺傳性血管性水腫（英语：hereditary angioedema）及其他疾病的藥物^[8]^[1]^[10]^[11]^[12]，主要經口服给药^[1]。

達那唑具有雄性化的副作用，使其用途大受限制。常見不良反應包含痤疮、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（英语：Antigonadotropin）、弱固醇類合成抑制劑（英语：steroidogenesis inhibitor），以及功能性抗動情素藥物（英语：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（英语：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

^ ^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）.
^ J.P. Griffin; P.F. D'Arcy. A Manual of Adverse Drug Interactions. Elsevier. 17 November 1997: 194– [2019-10-09]. ISBN 978-0-08-052583-9. （原始内容存档于2021-08-28）.
^ ^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.
^ ^4.0 ^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）.
^ ^5.0 ^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）.
^ ^6.0 ^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）.
^ 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）.
^ ^8.0 ^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）.
^ ^9.0 ^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
^ J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 345–. ISBN 978-1-4757-2085-3.
^ 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）.
^ 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.
^ 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.
^ ^14.0 ^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）.
^ 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）.
^ 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
^ Alan N. Elias; Grant Gwinup. Hirsutism. Praeger. 1 January 1983: 70 [2019-10-09]. （原始内容存档于2017-03-28）.
^ 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.

延伸閱讀

Dmowski WP. Endocrine properties and clinical application of danazol. Fertil. Steril. March 1979, 31 (3): 237–51. PMID 374128. doi:10.1016/S0015-0282(16)43869-0.
Fraser IS. Danazol--a steroid with a unique combination of actions. Scott Med J. April 1979, 24 (2): 147–50. PMID 386503. doi:10.1177/003693307902400209.
Potts GO, Schane HP, Edelson J. Pharmacology and pharmacokinetics of danazol. Drugs. May 1980, 19 (5): 321–30. PMID 6993179. doi:10.2165/00003495-198019050-00001.
Jenkin G. Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. May 1980, 20 (2): 113–8. PMID 6998453. doi:10.1111/j.1479-828X.1980.tb00107.x.
Barbieri RL, Ryan KJ. Danazol: endocrine pharmacology and therapeutic applications. Am. J. Obstet. Gynecol. October 1981, 141 (4): 453–63. PMID 7025640. doi:10.1016/0002-9378(81)90611-6.
Dmowski WP. Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. January 1990, 35 (1 Suppl): 69–74; discussion 74–5. PMID 2404115.
Barbieri RL. Danazol: molecular, endocrine, and clinical pharmacology. Prog. Clin. Biol. Res. 1990, 323: 241–52. PMID 2406750.
Hughes E, Brown J, Tiffin G, Vandekerckhove P. Danazol for unexplained subfertility. Cochrane Database Syst Rev. January 2007, (1): CD000069. PMID 17253444. doi:10.1002/14651858.CD000069.pub2.
Beaumont H, Augood C, Duckitt K, Lethaby A. Danazol for heavy menstrual bleeding. Cochrane Database Syst Rev. July 2007, (3): CD001017. PMID 17636649. doi:10.1002/14651858.CD001017.pub2.
Selak V, Farquhar C, Prentice A, Singla A. Danazol for pelvic pain associated with endometriosis. Cochrane Database Syst Rev. October 2007, (4): CD000068. PMID 17943735. doi:10.1002/14651858.CD000068.pub2.
Craig TJ. Appraisal of danazol prophylaxis for hereditary angioedema. Allergy Asthma Proc. 2008, 29 (3): 225–31. PMID 18387221. doi:10.2500/aap.2008.29.3107.
Ke LQ, Yang K, Li J, Li CM. Danazol for uterine fibroids. Cochrane Database Syst Rev. July 2009, (3): CD007692. PMID 19588442. doi:10.1002/14651858.CD007692.pub2.
Letchumanan P, Thumboo J. Danazol in the treatment of systemic lupus erythematosus: a qualitative systematic review. Semin. Arthritis Rheum. February 2011, 40 (4): 298–306. PMID 20541792. doi:10.1016/j.semarthrit.2010.03.005.

[DanocrineLabel-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）.

[GriffinD'Arcy1997-2] J.P. Griffin; P.F. D'Arcy. A Manual of Adverse Drug Interactions. Elsevier. 17 November 1997: 194– [2019-10-09]. ISBN 978-0-08-052583-9. （原始内容存档于2021-08-28）.

[NieschlagBehre2010-3] 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.

[ThomasRock2012-4] 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）.

[LemkeWilliams2012-5] 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）.

[Dörwald2013-6] 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）.

[Kurman2013-7] 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）.

[Martindale2013-8] 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）.

[JonesRock2015-9] 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

[Elks2014-10] J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 345–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-11] 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）.

[MortonHall2012-12] 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.

[Farquhar2007-13] 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.

[Lupulescu1990-14] 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）.

[AltchekDeligdisch20032-15] 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）.

[NeumannPotts19792-16] 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

[EliasGwinup19832-17] Alan N. Elias; Grant Gwinup. Hirsutism. Praeger. 1 January 1983: 70 [2019-10-09]. （原始内容存档于2017-03-28）.

[Dmowski19712-18] 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.

[8]

[1]

[10]

[11]

[12]

[2]

[3]

[4]

[5]

[9]

[6]

[7]

[13]

[14]

[15]

[16]

[17]

[18]