基本情報
- CAS
52806-53-8- 標準SMILES
CC(C)(O)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1- InChIKey
YPQLFJODEKMJEF-UHFFFAOYSA-N- 分子式
- C11H11F3N2O4
- 平均分子量
- 292.21 g/mol
- 単同位体質量
- 292.06709132
概要
2-hydroxyflutamide is a metabolite of flutamide. Flutamide is an oral nonsteroidal antiandrogen drug primarily used to treat prostate cancer. It competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. By doing so, it prevents them from stimulating the prostate cancer cells to grow. Flutamide has been largely replaced by a newer member of this class, bicalutamide, due to a better side-effect profile. (Wikipedia)
名称と識別子
- 優先名称
- Hydroxyflutamide
- IUPAC
- 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
- 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
- 英語名
- Hydroxyflutamide
- 分子式
- C11H11F3N2O4
- 分子量
- 292.21
名称と別名
名称をさらに表示
データベース識別子
- CAS
52806-53-8- PubChem CID
- 91649
- DTXSID
DTXSID8033562- ChEMBL
CHEMBL491- UNII
- 31D90UKP5Y
- EC Number
- 641-868-6
- Nikkaji
- J275.223I
物性
構造計算による物性
- XLogP
- 2.2
- 極性表面積
- 95.2 Ų
- 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
実験および物理化学的性質
物理化学的性質
- 融点
- 125 · 125-130°C
- 沸点
- 443.8 · 443.8±45.0 °C(Predicted)
- 比重(密度)
- 1.472 · 1.472
- 貯蔵温度
- room temp
- 溶解性
- 10 mg/mL · DMSO：>10mg/mL
- 酸解離定数(Pka)
- 12.87 · 12.87±0.70(Predicted)
- 外見
- 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
化学的性質
化学的特性HYDROXYFLUTAMIDE is Yellow-Brown Powder
安全と法規制
GHS分類
GHS Classification
Danger
H302 (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.
危険有害性情報
毒性情報
Toxicity Summary
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)
安全データ
- wgk
- 3
- rtecs
- TX1466250
- hs_code
- 2924297099
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36/37/39
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
用途と製造
応用分野
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.
上流・下流製品情報
上流原料
サプライヤー85 社
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