5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione

• ChemBase编号: 547
• 分子式: C12H10F3N3O4
• 平均质量: 317.2207096
• 单一同位素质量: 317.06234048
• SMILES: FC(F)(F)c1cc(N2C(=O)C(NC2=O)(C)C)ccc1[N+](=O)[O-]
• Canonical SMILES: O=C1NC(C(=O)N1c1ccc(c(c1)C(F)(F)F)[N+](=O)[O-])(C)C
• InChI: InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)
• InChIKey: XWXYUMMDTVBTOU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
• IUPAC传统名: nilutamide; 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
• 商标名: Anandron; Nilandron; Nilandrone; Nilutamida [Spanish]; Nilutamide [Usan:Ban:Inn]; Nilutamidum [Latin]
• 别名: Nilutamide; 5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedion; 1-3-Trifluoromethyl-4-nitrophenyl)-4,4-dimethylimidazoline-2,5-dione; Nilandron; Nilandrone; RU 23908; RU 23908-10; 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-2,4-imidazolidinedione; 5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione; Anandron; RU-23908; Nilutamide

登记号

• CAS号: 63612-50-0
• MDL号: MFCD00864670
• PubChem SID: 160964010; 46505381; 24278596
• PubChem CID: 4493

理论计算性质

JChem

• Acid pKa: 15.008641
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 2.2507768
• LogD (pH = 7.4): 2.2507768
• Log P: 2.2507768
• 摩尔折射率: 67.2218 cm^3
• 极化性: 24.620682 Å^3
• 极化表面积: 92.55 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.74
• LOG S: -4.88
• 溶解度: 4.19e-03 g/l

分子性质

理化性质

• 溶解度: Chloroform; Dichloromethane; Methanol
• 外观: Pale Yellow Solid; solid
• 熔点: 153-154°C
• 疏水性(logP): 1.8

安全信息

• 保存条件: Refrigerator
• RTECS编号: NI9453300
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 60-25
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H360
• GHS警示性声明: P201-P301 + P310-P308 + P313
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 相关基因信息: human ... AR(367)
• 生物活性机理: Androgen receptor blocker, preventing its interaction with testosterone

产品相关信息

• 纯度: 97%
• 应用领域: Antineoplastic agent; Used for treatment of prostatic cancer
• Empirical Formula (Hill Notation): C12H10F3N3O4

详细说明

DrugBank - DB00665

• Drug Groups: approved
• Description: Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration.
• Indication: For use in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2).
• Pharmacology: Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration. The relative binding affinity of nilutamide at the androgen receptor is less than that of bicalutamide, but similar to that of hydroxuflutamide.
• Toxicity: Symptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: The results of a human metabolism study using 14C-radiolabelled tablets show that nilutamide is extensively metabolized and less than 2% of the drug is excreted unchanged in urine after 5 days.
• Absorption: Rapidly and completely absorbed, yielding high and persistent plasma concentrations.
• Half Life: 38.0-59.1 hours
• Elimination: Nilutamide is extensively metabolized andless than 2% of the drug is excreted unchanged in urine after 5 days. Fecal elimination is negligible, ranging from 1.4% to 7% of the dose after 4 to 5 days.
• References: Kassouf W, Tanguay S, Aprikian AG: Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J Urol. 2003 May;169(5):1742-4. [Pubmed] ; Lukka H, Waldron T, Klotz L, Winquist E, Trachtenberg J: Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review. Curr Oncol. 2006 Jun;13(3):81-93. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - N8534

Biochem/physiol Actions
Nilutamide is an antiandrogen used in the treatment of prostate cancer.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N8534.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - N467500

Nonsteroidal antiandrogen. Antineoplastic (hormonal).

参考文献

• Kassouf W, Tanguay S, Aprikian AG: Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J Urol. 2003 May;169(5):1742-4. Pubmed
• Lukka H, Waldron T, Klotz L, Winquist E, Trachtenberg J: Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review. Curr Oncol. 2006 Jun;13(3):81-93. Pubmed
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