(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

• ChemBase编号: 1215
• 分子式: C22H27NO2
• 平均质量: 337.45528
• 单一同位素质量: 337.20417911
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=Cc5oncc5C4)CC3)C)CC2)CC1)C)C#C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=Cc3c(C[C@]12C)cno3
• 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
• InChIKey: POZRVZJJTULAOH-LHZXLZLDSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^2,^1^0.0^4,^8.0^1^4,^1^8]icosa-4(8),5,9-trien-17-ol; (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol
• IUPAC传统名: danazol
• 商标名: Anatrol; Chronogyn; Cyclomen; Danocrine
• 别名: 17β-hydroxy-2,4,17α-pregnadien-20-yno[2,3-D]isoxazole; (17α)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol; 17α-Ethynyl-17β-hydroxy-4-androsteno[2,3-d]isoxazole; Win-17757; Bonzol; Cyclomen; Danatrol; Danocrine; Danol; Danazol; 17β-Hydroxy-2,4,17α-pregnadien-20-yno[2,3-d]-isoxazole; 2,4,17α-Pregnadien-20-yno[2,3-d]-isoxa-zol-17-ol

登记号

• CAS号: 17230-88-5
• EC号: 241-270-1
• PubChem SID: 160964675; 46506475
• PubChem CID: 28417
• CHEBI ID: 4315
• ATC码: G03XA01
• CHEMBL: 1479
• Chemspider ID: 26436
• DrugBank ID: DB01406
• KEGG ID: D00289
• 美国药典/FDA物质标识码: N29QWW3BUO
• 维基百科标题: Danazol
• Medline Plus: a682599

理论计算性质

JChem

• Acid pKa: 17.594933
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.4620798
• LogD (pH = 7.4): 3.4620821
• Log P: 3.4620821
• 摩尔折射率: 98.5352 cm^3
• 极化性: 37.660843 Å^3
• 极化表面积: 46.26 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.62
• LOG S: -4.28
• 溶解度: 1.76e-02 g/l

分子性质

理化性质

• 溶解度: Acetonitrile; Chloroform; Ethanol
• 外观: Off-White to Pale Yellow Solid
• 熔点: 218-2200C; 225°C (dec.)
• 疏水性(logP): 0.51 [PERRISSOUD,D & TESTA,B (1986)]

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: TU4157070
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 危险公开号: R:36/37/38
• 安全公开号: S:20-25-26-37/39

药理学性质

• 给药途径: Oral
• 半衰期: 15 hours
• 代谢: Hepatic
• 法定药品分级: Rx-only (US); S4 (Australia)
• 妊娠期药物分类: D (Australia); X (US)

产品相关信息

• 分类: Rare Derivatives of Natural Compounds

详细说明

DrugBank - DB01406

• Drug Groups: approved
• Description: A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders. [PubChem]
• Indication: For the treatment of endometriosis and fibrocystic breast disease (in patients unresponsive to simple measures). Also used for the prophylactic treatment of all types of hereditary angioedema in males and females.
• Pharmacology: Danazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. It was approved by the U.S. Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis, but its role as a treatment for endometriosis has been largely replaced by the gonadotropin-releasing hormone (GnRH) agonists. Danazol has antigonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.
• Half Life: Approximately 24 hours.
• References: Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Pubmed] ; Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [Pubmed] ; Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - D145000

Danazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin.

参考文献

• Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. Pubmed
• Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. Pubmed
• Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. Pubmed
• Ahn, Y.S., et al.: N. Engl. J. Med., 308, 1396 (1983)