기본 정보
- CAS
52806-53-8- 표준 SMILES
CC(C)(O)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1- InChIKey
YPQLFJODEKMJEF-UHFFFAOYSA-N- 분자식
- C11H11F3N2O4
- 평균 분자량
- 292.21 g/mol
- 단동위원소 질량
- 292.06709132
개요
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)
이름 및 식별자
- 우선 이름
- Hydroxyflutamide
- IUPAC
- 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
- 현지명
- 하이드록시플루타미드
- 영어명
- Hydroxyflutamide
- 분자식
- C11H11F3N2O4
- 분자량
- 292.21
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
52806-53-8- PubChem CID
- 91649
- DTXSID
DTXSID8033562- ChEMBL
CHEMBL491- UNII
- 31D90UKP5Y
- EC Number
- 641-868-6
- Nikkaji
- J275.223I
물성
구조 계산 물성
- XLogP
- 2.2
- 극성 표면적
- 95.2 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 7
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 20
- 형식 전하
- 0
- 복잡도
- 392
실험 및 물리화학적 성질
물리화학적 성질
- 녹는점
- 125 · 125-130°C
- 끓는 점
- 443.8 · 443.8±45.0 °C(Predicted)
- 밀도
- 1.472 · 1.472
- 저장 조건
- room temp
- 용해도
- 10 mg/mL · DMSO: >10mg/mL
- 산도 계수 (pKa)
- 12.87 · 12.87±0.70(Predicted)
- 물리적 상태
- 가루
- 색상
- 흰색에서 황갈색까지
- 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
화학적 성질
HYDROXYFLUTAMIDE is Yellow-Brown Powder
안전 및 규제
GHS 분류
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.
유해성 정보
독성 정보
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)
안전 데이터
- wgk
- 3
- rtecs
- TX1466250
- HS 번호
- 2924297099
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36/37/39
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
용도 및 제조
응용 분야
개요2-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.
용도HYDROXYFLUTAMIDE is used non-steroidal antagonist Flutamide. Shown to be an antianhydrogen.
상·하류 제품 정보
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