2-ヒドロキシ-2-メチル-N-(4-ニトロ-3-トリフルオロメチルフェニル)プロピオンアミド
ヒドロキシフルタミド · 2-ヒドロキシフルタミド · 2-ヒドロキシ-2-メチル-N-(3-トリフルオロメチル-4-ニトロフェニル)プロパンアミド · 2-ヒドロキシ-2-メチル-N-(4-ニトロ-3-トリフルオロメチルフェニル)プロピオンアミド · N-[3-(トリフルオロメチル)-4-ニトロフェニル]-2-ヒドロキシイソブチルアミド · 2-ヒドロキシ-2-メチル-N-[4-ニトロ-3-(トリフルオロメチル)フェニル]プロパンアミド · 2-メチル-2-ヒドロキシ-N-[4-ニトロ-3-(トリフルオロメチル)フェニル]プロパンアミド · 2-ヒドロキシ-2-メチル-N-[4-ニトロ-3-(トリフルオロメチル)フェニル]プロピオンアミド
識別子と物理属性
| CAS No. | 52806-53-8 |
|---|---|
| 分子式 | C11H11F3N2O4 |
| 平均分子量 | 292.21 g/mol |
| 単同位体質量 | 292.06709132 g/mol |
| SMILES | CC(C)(O)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1 |
| InChIKey | YPQLFJODEKMJEF-UHFFFAOYSA-N |
| PubChem CID | 91649 |
| ChEMBL | CHEMBL491 |
| EC No. | 641-868-6 |
| DTXSID | DTXSID8033562 |
| 現地名 | 2-ヒドロキシ-2-メチル-N-(4-ニトロ-3-トリフルオロメチルフェニル)プロピオンアミド |
化学・物理的性質
| XLogP | 2.2 |
|---|---|
| 極性表面積 | 95.2 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 7 |
| 回転可能結合数 | 2 |
| 重原子数 | 20 |
| 形式電荷 | 0 |
| 複雑度 | 392 |
| LogP（分配係数） | 2.7 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Collision Cross Section | 157.4 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID8033562] |
| 融点 | 125-130°C |
| 沸点 | 443.8±45.0 °C(Predicted) |
| 密度 | 1.472 |
| 貯蔵条件 | room temp |
| 溶解度 | DMSO：>10mg/mL |
| pKa（酸解離定数） | 12.87±0.70(Predicted) |
| 外観・状態 | 粉 |
| 色 | 白から黄褐色 |
| InChI | 1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17) |
| InChIKey | YPQLFJODEKMJEF-UHFFFAOYSA-N |
| SMILES | CC(C)(O)C(=O)Nc1ccc(c(c1)C(F)(F)F)[N+]([O-])=O |
化学的特性
HYDROXYFLUTAMIDE is Yellow-Brown Powder
安全性と法規制
| GHS 分類 | DangerH302 (55.7%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 88 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (55.7%) |
| 健康影響 | Environmental antiandrogens can have harmful effects on reproductive organ development in fetuses exposed in utero as well as their offspring. (Wikipedia) |
| 毒性の概要 | Hydroxyflutamide is an antiandrogen. Antiandrogens alter the androgen pathway by blocking the appropriate receptors, competing for binding sites on the cell's surface, or affecting androgen production. Antiandrogens are classified as steroidal or nonsteroidal. Steroidal antiandrogens not only counter androgens, but also affect secondary sex characteristics. Steroidal antiandrogens directly affect gene expression due to their fat-soluble nature that allows them to diffuse through the plasma membrane's phospholipid bilayer and prevent the binding of testosterone and dihydrotestosterone (DHT) to the androgen receptor. Inhibition of androgen production occurs through a unique mechanism for each antiandrogen. (Wikipedia) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | TX1466250 |
| 税関コード | 2924297099 |
| 危険文句（R） | 36/37/38 |
| 危険表示 | Xi |
| 安全措置（S） | 26-36/37/39 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
2-hydroxy Flutamide is the major metabolite formed during the metabolism of the non-steroidal antiandrogen flutamide by cytochrome P450 (CYP) isoforms CYP1A2 and CYP3A4. Through competitive inhibition of the binding of testosterone to the nuclear androgen receptor (AR; IC50 = ~300-900), 2-hydroxy flutamide blocks the expression of AR target genes and prevents androgen-dependent stabilization of the AR. Compared to flutamide, 2-hydroxy flutamide is a more potent antiandrogen in vivo, demonstrating a higher binding affinity for the AR (0.1% binding affinity relative to dihydrotestosterone) and, thus, is the predominant contributor to the therapeutic effects of flutamide in the treatment of prostate cancer.
使用
HYDROXYFLUTAMIDE is used non-steroidal antagonist Flutamide. Shown to be an antianhydrogen.