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sulfadiazine (CHEBI:9328)

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ChEBI Name sulfadiazine
ChEBI ID CHEBI:9328
Definition A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula Source
C10H10N4O2S ChEBI
Net Charge 0
Average Mass 250.27700
InChI
InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
InChIKey
SEEPANYCNGTZFQ-UHFFFAOYSA-N
SMILES
Nc1ccc(cc1)S(=O)(=O)Nc1ncccn1
Roles Classification
Chemical Role(s): EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the activity of sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming), EC 1.1.1.153, which plays an important part in the biosynthesis of tetrahydrobiopterin.
EC 2.5.1.15 (dihydropteroate synthase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of dihydropteroate synthase (EC 2.5.1.15), an enzyme that catalyzes the formation of dihydropteroate from p-aminobenzoic acid and dihydropteridine-hydroxymethyl-pyrophosphate.
Biological Role(s): coccidiostat
An agent useful in the treatment or prevention of coccidiosis in man or animals.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the activity of sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming), EC 1.1.1.153, which plays an important part in the biosynthesis of tetrahydrobiopterin.
antibiotic
A substance that is biostatic or biocidal at low concentrations towards bacteria, yeasts, moulds, or other form of life, especially pathogenic or noxious organisms. Although the term was originally restricted to substances produced by microorganisms, its use was later expanded to include derivatives of such substances and it is now commonly used to include entirely synthetic compounds.
EC 2.5.1.15 (dihydropteroate synthase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of dihydropteroate synthase (EC 2.5.1.15), an enzyme that catalyzes the formation of dihydropteroate from p-aminobenzoic acid and dihydropteridine-hydroxymethyl-pyrophosphate.
Application(s): coccidiostat
An agent useful in the treatment or prevention of coccidiosis in man or animals.
antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
antibiotic
A substance that is biostatic or biocidal at low concentrations towards bacteria, yeasts, moulds, or other form of life, especially pathogenic or noxious organisms. Although the term was originally restricted to substances produced by microorganisms, its use was later expanded to include derivatives of such substances and it is now commonly used to include entirely synthetic compounds.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing sulfadiazine (CHEBI:9328) has functional parent sulfanilamide (CHEBI:45373)
sulfadiazine (CHEBI:9328) has role antibiotic (CHEBI:22582)
sulfadiazine (CHEBI:9328) has role antiinfective agent (CHEBI:35441)
sulfadiazine (CHEBI:9328) has role antiprotozoal drug (CHEBI:35820)
sulfadiazine (CHEBI:9328) has role coccidiostat (CHEBI:35818)
sulfadiazine (CHEBI:9328) has role EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor (CHEBI:74234)
sulfadiazine (CHEBI:9328) has role EC 2.5.1.15 (dihydropteroate synthase) inhibitor (CHEBI:50502)
sulfadiazine (CHEBI:9328) is a pyrimidines (CHEBI:39447)
sulfadiazine (CHEBI:9328) is a sulfonamide (CHEBI:35358)
sulfadiazine (CHEBI:9328) is conjugate acid of sulfadiazinate (CHEBI:33127)
Incoming sulfadiazinate (CHEBI:33127) is conjugate base of sulfadiazine (CHEBI:9328)
IUPAC Name
4-amino-N-(pyrimidin-2-yl)benzenesulfonamide
INNs Sources
sulfadiazina WHO MedNet
sulfadiazine WHO MedNet
sulfadiazine WHO MedNet
sulfadiazinum WHO MedNet
Synonyms Sources
2-sulfanilamidopyrimidine NIST Chemistry WebBook
2-sulfanilylaminopyrimidine NIST Chemistry WebBook
4-amino-N-2-pyrimidinylbenzenesulfonamide NIST Chemistry WebBook
N1-2-pyrimidinylsulfanilamide NIST Chemistry WebBook
N1-2-pyrimidylsulfanilamide NIST Chemistry WebBook
Sulfadiazine KEGG COMPOUND
sulfapyrimidine ChemIDplus
sulphadiazine NIST Chemistry WebBook
Database Links Databases
C07658 KEGG COMPOUND
D00587 KEGG DRUG
DB00359 DrugBank
GB557055 Patent
HMDB14503 HMDB
Sulfadiazine Wikipedia
US2407966 Patent
US2410793 Patent
View more database links
Registry Numbers Types Sources
219136 Gmelin Registry Number Gmelin
235192 Reaxys Registry Number Reaxys
235192 Beilstein Registry Number Beilstein
68-35-9 CAS Registry Number NIST Chemistry WebBook
68-35-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11431418 PubMed citation CiteXplore
12811231 PubMed citation CiteXplore
13037579 PubMed citation CiteXplore
15907564 PubMed citation CiteXplore
18706672 PubMed citation CiteXplore
20244050 PubMed citation CiteXplore
23206954 PubMed citation CiteXplore
23245764 PubMed citation CiteXplore
23270807 PubMed citation CiteXplore
23322489 PubMed citation CiteXplore
23396336 PubMed citation CiteXplore
23411088 PubMed citation CiteXplore
23411170 PubMed citation CiteXplore
23704574 PubMed citation CiteXplore
23707894 PubMed citation CiteXplore
7378112 PubMed citation CiteXplore
8429812 PubMed citation CiteXplore
Last Modified
22 July 2014

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