기본 정보
- CAS
526-08-9- 표준 SMILES
Nc1ccc(S(=O)(=O)Nc2ccnn2-c2ccccc2)cc1- InChIKey
QWCJHSGMANYXCW-UHFFFAOYSA-N- 분자식
- C15H14N4O2S
- 평균 분자량
- 314.4 g/mol
- 단동위원소 질량
- 314.08374688
개요
Sulfaphenazole is a sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent. It has a role as an antibacterial drug, a P450 inhibitor, an EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor and an EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor. It is a member of pyrazoles, a sulfonamide, a substituted aniline, a primary amino compound and a sulfonamide antibiotic.
이름 및 식별자
- 우선 이름
- Sulfaphenazole
- IUPAC
- 4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide
- 영어명
- SULFAPHENAZOLE
- 분자식
- C15H14N4O2S
- 분자량
- 314.36
이름 및 동의어
sulfaphenazole526-08-9SulphaphenazoleSulfabid4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamideSulfafenazolSulfaphenazolSulfaphenazolumSulfafenazoloSulfaphenylpyrazol1-Phenyl-5-sulfanilamidopyrazole5-Sulfanilamido-1-phenylpyrazole
이름 더 보기
SPTFF2Trefoil factor 2SulfaphenylpyrazoleSML1OrisulInamil
N'-(1-Phenylpyrazol-5-yl)sulfanilamide4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamidePhenylsulfapyrazoleOrisulf3-(p-Aminobenzenesulfonamido)-2-phenylpyrazoleBenzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-DTXSID20441314-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-sulfonamide
데이터베이스 식별자
- CAS
526-08-9- PubChem CID
- 5335
- DTXSID
DTXSID2044131- ChEMBL
CHEMBL1109- ChEBI
CHEBI:77780- UNII
- 0J8L4V3F81
물성
구조 계산 물성
- XLogP
- 1.5
- 극성 표면적
- 98.4 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 22
- 형식 전하
- 0
- 복잡도
- 451
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP
1.52
1.35
Solubility0.6 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point101 °C
Physical DescriptionSolid
Collision Cross Section
157.93 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
170 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 179 · 179-183 °C
- 끓는 점
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
안전 데이터
- wgk
- 2
- rtecs
- DA9520000
- 독성
- LD50 orally in mice: 5800 mg/kg (Seki)
- HS 번호
- 29339900
- safety_code
- 24/25
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
S - Sensory organs
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QS - Sensory organs
Mechanism of Action
Sulfaphenazole is a sulfonamide antibacterial. In bacteria, antibacterial sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis. As such, the microorganism will be "starved" of folate and die.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Cellular LocationsMembrane
용도 및 제조
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
응용 분야
개요CYP2C9 is a major cytochrome P450 enzyme that is involved in the metabolic clearance of various therapeutic agents. Disruption of this enzyme’s activity can lead to adverse drug reactions. Sulfaphenazole is an inhibitor of CYP2C9 (Ki = 0.3 μM) that demonstrates at least 100-fold selectivity over other CYP450 isoforms (Kis = 63 and 29 μM for CYP2C8 and CYP2C18, respectively, and no activity at CYP1A1, CYP1A2, CYP3A4, CYP2C19). At 10 μM, sulfaphenazole has been shown to inhibit endothelium-derived hyperpolarizing factor synthase, a CYP450 isozyme in the porcine coronary artery homologous to CYP2C8/9 that generates reactive oxygen species in coronary endothelial cells and modulates vascular tone and homeostasis.
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