2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

• ChemBase编号: 382
• 分子式: C11H11F3N2O3
• 平均质量: 276.2118496
• 单一同位素质量: 276.07217688
• SMILES: FC(F)(F)c1cc(NC(=O)C(C)C)ccc1[N+](=O)[O-]
• Canonical SMILES: O=C(C(C)C)Nc1ccc(c(c1)C(F)(F)F)[N+](=O)[O-]
• InChI: InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
• InChIKey: MKXKFYHWDHIYRV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• IUPAC传统名: flutamide
• 商标名: Cebatrol; Eulexin; Niftholide; Niftolide
• 别名: Eulexin; Flutamin; Drogenil; FTA; Flutamide USP25; Flutamide; 2-Methyl-N-(4-nitro-3-[trifluoromethyl]phenyl)propanamide; Flutamide; 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide; N-(Isopropylcarbonyl)-4-nitro-3-trifluoromethylaniline; 4'-Nitro-3'-trifluoromethylisobutyranilide; Drognil; Euflex; Sch 13521; Flutamide; 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

登记号

• CAS号: 13311-84-7
• EC号: 236-341-9
• MDL号: MFCD00072009
• PubChem SID: 46508874; 160963845; 24278446
• PubChem CID: 3397

理论计算性质

JChem

• Acid pKa: 13.17286
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.272311
• LogD (pH = 7.4): 3.2723103
• Log P: 3.272311
• 摩尔折射率: 63.4208 cm^3
• 极化性: 22.133842 Å^3
• 极化表面积: 74.92 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.55
• LOG S: -4.69
• 溶解度: 5.66e-03 g/l

分子性质

理化性质

• 溶解度: 9.45 mg/L; DMSO; Methanol
• 外观: Light Yellow Solid
• 熔点: 110-112°C
• 疏水性(logP): 2.6; 3.335

安全信息

• 保存条件: -20°C; Refrigerator
• 保存注意事项: Irritant
• RTECS编号: UG5700000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63-20/21/22
• 安全公开号: 22-36
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332-H361
• GHS警示性声明: P280
• 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

药理学性质

• 相关基因信息: human ... AR(367)mouse ... Ar(11835)rat ... Ar(24208)

产品相关信息

• 纯度: 95%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C11H11F3N2O3

详细说明

DrugBank - DB00499

• Drug Groups: approved
• Description: An antiandrogen with about the same potency as cyproterone in rodent and canine species.
• Indication: For the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate
• Pharmacology: Flutamide is a nonsteroidal antiandrogen. In animal studies, flutamide demonstrates potent antiandrogenic effects. It exerts its antiandrogenic action by inhibiting androgen uptake and/or by inhibiting nuclear binding of androgen in target tissues or both. Prostatic carcinoma is known to be androgen-sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen, e.g. castration. Elevations of plasma testosterone and estradiol levels have been noted following flutamide administration.
• Toxicity: In animal studies with flutamide alone, signs of overdose included hypoactivity, piloerection, slow respiration, ataxia, and/or lacrimation, anorexia, tranquilization, emesis, and methemoglobinemia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Flutamide is rapidly and extensively metabolized, with flutamide comprising only 2.5% of plasma radioactivity 1 hour after administration.
• Absorption: Rapidly and completely absorbed.
• Half Life: The plasma half-life for the alpha-hydroxylated metabolite of flutamide (an active metabolite) is approximately 6 hours.
• Protein Binding: 94-96%
• Elimination: Flutamide and its metabolites are excreted mainly in the urine with only 4.2% of a single dose excreted in the feces over 72 hours.
• References: [Link]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1908

Research Area: Cancer
Biological Activity:
Flutamide (Eulexin, Flutamin) is an oral nonsteroidal antiandrogen agent primarily used to treat prostate cancer. Flutamide (Eulexin, Flutamin) competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. By doing so, flutamide (Eulexin, Flutamin) prevents them from stimulating the prostate cancer cells to grow. [1]

Sigma Aldrich - F9397

Biochem/physiol Actions
Flutamide is a non-steroidal anti-androgen.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F9397.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - F598850

Flutamide is a nonsteroidal antiandrogen drug; antineoplastic (hormonal).

参考文献

• Link
• http://en.wikipedia.org/wiki/Flutamide
• Neri, et al.: Endocrinology, 91, 427 (1972)
• Sogani, P.C., et al.: J. Urol., 122, 640 (1972)
• Greenway, B.A., et al.: Br. Med. J., 316, 1935 (1972)