(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

• ChemBase编号: 503
• 分子式: C19H30O3
• 平均质量: 306.4397
• 单一同位素质量: 306.21949482
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@@H](CC3)CC(=O)OC4)C)CC2)CC1)C)C
• Canonical SMILES: O=C1OC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C)O)C)C
• InChI: InChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1
• InChIKey: QSLJIVKCVHQPLV-PEMPUTJUSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one; (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC传统名: oxandrolone
• 商标名: Anavar; Lonavar; Oxandrin; Protivar; Provitar; Vasorome
• 别名: Ossandrolone [DCIT]; Oxandrolona [INN-Spanish]; Oxandrolonum [INN-Latin]; oxandrolone; Oxandrolone; 17β-Hydroxy-17-methyl-2-oxa-5α-androstan-3-one; (5α,17β)-17-Hydroxy-17-methyl-2-oxaandrostan-3-one; 17-Methyl-2-oxa-5α-androstan-17β-ol-3-one; Lonavar; NSC 67068; Oxandren; Protivar; Provitar; SC 11585; Vasorome; Oxandrin; Anavar

登记号

• CAS号: 53-39-4
• PubChem SID: 160963966; 46509027
• PubChem CID: 5878
• CHEBI ID: 7820
• ATC码: A14AA08
• CHEMBL: 1200436
• Chemspider ID: 5667
• DrugBank ID: DB00621
• KEGG ID: D00462
• 美国药典/FDA物质标识码: 7H6TM3CT4L
• 维基百科标题: Oxandrolone
• Medline Plus: a604024

理论计算性质

ALOGPS 2.1

• Log P: 3.36
• LOG S: -4.34
• 溶解度: 1.40e-02 g/l

JChem

• Log P: 2.9536674
• 摩尔折射率: 84.749 cm^3
• 极化性: 34.19302 Å^3
• 极化表面积: 46.53 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 2.9536672
• LogD (pH = 7.4): 2.9536674

分子性质

理化性质

• 溶解度: Chloroform
• 外观: White Solid
• 熔点: 214-217°C
• 疏水性(logP): 4.2

安全信息

• 保存条件: -20°C; Controlled Substance, -20°C Freezer

药理学性质

• 给药途径: Oral
• 生物利用度: 97%
• 排泄: Urinary:90%; Fecal:7%
• 半衰期: 9 hours
• 代谢: Hepatic
• 法定药品分级: Schedule III (US)
• 妊娠期药物分类: X

产品相关信息

• 成盐信息: Free Base

详细说明

DrugBank - DB00621

• Drug Groups: approved; investigational
• Description: A synthetic hormone with anabolic and androgenic properties. [PubChem]
• Indication: Use to promote weight gain after weight loss following extensive surgery.
• Pharmacology: Oxandrolone is an anabolic steroids indicated as adjunctive therapy to promote weight gain after weight loss following extensive surgery, chronic infections, or severe trauma, and in some patients who without definite pathophysiologic reasons fail to gain or to maintain normal weight, to offset the protein catabolism associated with prolonged administration of corticosteroids, and for the relief of the bone pain frequently accompanying osteoporosis. Anabolic steroids are synthetic derivatives of testosterone.
• Toxicity: The oral LD50 of oxandrolone in mice and dogs is greater than 5,000 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Renal
• Half Life: 0.55 hours (1st phage), 9 hours (2nd phase)
• References: Demling RH, DeSanti L: Oxandrolone induced lean mass gain during recovery from severe burns is maintained after discontinuation of the anabolic steroid. Burns. 2003 Dec;29(8):793-7. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1753

Related research area: Endocrinology

Toronto Research Chemicals - O845050

A synthetic, anabolic steroid. Used to promote muscle growth and combat involuntary weight loss. It has also been used to treat cases of osteoporosis.

参考文献

• Demling RH, DeSanti L: Oxandrolone induced lean mass gain during recovery from severe burns is maintained after discontinuation of the anabolic steroid. Burns. 2003 Dec;29(8):793-7. Pubmed
• http://en.wikipedia.org/wiki/Oxandrolone
• Cadwallader, A., et al.: Mol. Pharm., 7, 689 (2010)
• Amundson, E., et al.: J. Clin. Endocrinol. Metabol., 95, 1355 (2010)
• Bovee, T., et al.: J. Steroid Biochem. Mol. Biol., 118, 85 (2010)
• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2010)