(1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase编号: 1056
• 分子式: C20H29FO3
• 平均质量: 336.4408632
• 单一同位素质量: 336.21007301
• SMILES: F[C@]12[C@H]([C@H]3[C@@]([C@@](O)(CC3)C)(C[C@@H]2O)C)CCC2=CC(=O)CC[C@]12C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1CC[C@]2(C)O)C)C
• InChI: InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1
• InChIKey: YLRFCQOZQXIBAB-RBZZARIASA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC传统名: fluoxymesterone
• 商标名: Anadroid-F; Android-f; Androsterolo; Fluosterone; Fluotestin; Flusteron; Flutestos; Halotestin; Neo-Ormonal; Ora Testryl; Ora-testryl; Oralsterone; Oratestin; Testoral; Ultandren; Ultandrene
• 别名: Fluossimesterone [DCIT]; Fluoximesterona [INN-Spanish]; Fluoximesterone; Fluoximesteronum; Fluoxymesteronum [INN-Latin]; Fluoxymestrone; Androfluorene; Androfluorone; FXM; Fluoxymesterone; 11β,17β-Dihydroxy-9α-fluoro-17α-methyl-4-androsten-3-one; 9α-Fluoro-11β,17β-dihydroxy-17α-methylandrost-4-en-3-one; 9α-Fluoro-11β-hydroxy-17α-methyltestosterone; Fluoxymesterone

登记号

• CAS号: 76-43-7
• EC号: 200-961-8
• MDL号: MFCD00010480
• PubChem SID: 24894947; 160964519; 46508867
• PubChem CID: 6446
• CHEBI ID: 5120
• ATC码: G03BA01
• CHEMBL: 1445
• Chemspider ID: 6205
• DrugBank ID: DB01185
• IUPHAR配体索引: 2861
• KEGG ID: D00327
• 美国药典/FDA物质标识码: 9JU12S4YFY
• 维基百科标题: Fluoxymesterone
• Medline Plus: a682690

理论计算性质

JChem

• Acid pKa: 13.601727
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 2.3808422
• LogD (pH = 7.4): 2.3808417
• Log P: 2.3808422
• 摩尔折射率: 90.1885 cm^3
• 极化性: 35.430447 Å^3
• 极化表面积: 57.53 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: 2.5
• LOG S: -3.87
• 溶解度: 4.52e-02 g/l

分子性质

理化性质

• 溶解度: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble6.4 mg/mL; 67.5 mg/L; ethanol: soluble7.3 mg/mL; H2O: ≤0.5 mg/mL
• 外观: white solid (photosensitive)
• 疏水性(logP): 2

安全信息

• RTECS编号: BV8390000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63
• 安全公开号: 22-36
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H361
• GHS警示性声明: P281
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• 毒品管制信息: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

药理学性质

• 生物利用度: 100% Oral
• 排泄: urine
• 半衰期: 9.5 hours
• 代谢: Hepatic
• 法定药品分级: Schedule III Controlled Substance
• 妊娠期药物分类: X
• 相关基因信息: human ... AR(367), ESR1(2099), PRLR(5618)

产品相关信息

• 纯度: 95%

详细说明

DrugBank - DB01185

• Drug Groups: illicit; approved
• Description: An anabolic steroid that has been used in the treatment of male hypogonadism, delayed puberty in males, and in the treatment of breast neoplasms in women. [PubChem]
• Indication: In males, used as replacement therapy in conditions associated with symptoms of deficiency or absence of endogenous testosterone. In females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal.
• Pharmacology: Fluoxymesterone is a synthetic androgen, or male hormone, similar to testosterone. Fluoxymesterone works by attaching itself to androgen receptors; this causes it to interact with the parts of the cell involved in the making of proteins. It may cause an increase in the synthesis of some proteins or a decrease in the synthesis of others. These proteins have a variety of effects, including blocking the growth of some types of breast cancer cells, stimulating cells that cause male sexual characteristics, and stimulating the production of red blood cells.
• Toxicity: Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Presence of 17-alpha alkyl group reduces susceptibility to hepatic enzyme degradation, which slows metabolism and allows oral administration. Inactivation of testosterone occurs primarily in the liver
• Absorption: Oral absorption is less than 44%.
• Half Life: 9.2 hours
• Protein Binding: Very high (99%) with 80% to sex hormone binding globulin, 19% to albumin.
• References: Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, Lopez FJ, Marschke KB, Rosen J, Schrader W, Turner R, van Oeveren A, Viveros H, Zhi L, Negro-Vilar A: An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Epub 2006 Oct 5. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - F7751

Biochem/physiol Actions
Fluoxymesterone is an androgen and anabolic steroid.

参考文献

• Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, Lopez FJ, Marschke KB, Rosen J, Schrader W, Turner R, van Oeveren A, Viveros H, Zhi L, Negro-Vilar A: An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Epub 2006 Oct 5. Pubmed