CHEBI:77780 - sulfaphenazole

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ChEBI Name sulfaphenazole
ChEBI ID CHEBI:77780
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H14N4O2S
Net Charge 0
Average Mass 314.36200
Monoisotopic Mass 314.084
InChI InChI=1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2
InChIKey QWCJHSGMANYXCW-UHFFFAOYSA-N
SMILES Nc1ccc(cc1)S(=O)(=O)Nc1ccnn1-c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of 13-deoxydaunorubicin hydroxylase (EC 1.14.13.181).
EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of quinine 3-monooxygenase (EC 1.14.13.67).
P450 inhibitor
An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via sulfonamide antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sulfaphenazole (CHEBI:77780) has role antibacterial drug (CHEBI:36047)
sulfaphenazole (CHEBI:77780) has role EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor (CHEBI:77781)
sulfaphenazole (CHEBI:77780) has role EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor (CHEBI:77783)
sulfaphenazole (CHEBI:77780) has role P450 inhibitor (CHEBI:50183)
sulfaphenazole (CHEBI:77780) is a primary amino compound (CHEBI:50994)
sulfaphenazole (CHEBI:77780) is a pyrazoles (CHEBI:26410)
sulfaphenazole (CHEBI:77780) is a substituted aniline (CHEBI:48975)
sulfaphenazole (CHEBI:77780) is a sulfonamide (CHEBI:35358)
sulfaphenazole (CHEBI:77780) is a sulfonamide antibiotic (CHEBI:87228)
IUPAC Name
4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide
INNs Sources
sulfafenazol WHO MedNet
sulfaphénazol WHO MedNet
sulfaphenazole WHO MedNet
sulfaphenazolum WHO MedNet
Synonyms Sources
1-phenyl-5-sulfanilamidopyrazole NIST Chemistry WebBook
3-(p-aminobenzenesulfonamido)-2-phenylpyrazole NIST Chemistry WebBook
5-sulfanilamido-1-phenylpyrazole NIST Chemistry WebBook
N'-(1-phenylpyrazol-5-yl)sulfanilamide NIST Chemistry WebBook
N1-(1-phenylpyrazol-5-yl)sulfanilamide ChemIDplus
sulphaphenazole KEGG DRUG
Brand Name Source
Sulfabid KEGG DRUG
Manual Xrefs Databases
2523 DrugCentral
D01954 KEGG DRUG
DB06729 DrugBank
HMDB0015667 HMDB
LSM-5279 LINCS
Sulfaphenazole Wikipedia
US2858309 Patent
View more database links
Registry Numbers Types Sources
308518 Reaxys Registry Number Reaxys
526-08-9 CAS Registry Number NIST Chemistry WebBook
526-08-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
13873771 PubMed citation Europe PMC
18845175 PubMed citation Europe PMC
22785021 PubMed citation Europe PMC
24519941 PubMed citation Europe PMC
9864343 PubMed citation Europe PMC
Last Modified
22 February 2017