CHEBI:102265 - sulfamethazine

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ChEBI Name sulfamethazine
Definition A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C12H14N4O2S
Net Charge 0
Average Mass 278.33000
Monoisotopic Mass 278.08375
InChI InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
SMILES Cc1cc(C)nc(NS(=O)(=O)c2ccc(N)cc2)n1
Roles Classification
Chemical Role(s): ligand
Any molecule or ion capable of binding to a central metal atom to form coordination complexes.
environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): EC (dihydropteroate synthase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of dihydropteroate synthase (EC, an enzyme that catalyzes the formation of dihydropteroate from p-aminobenzoic acid and dihydropteridine-hydroxymethyl-pyrophosphate.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via sulfonamide antibiotic )
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
drug allergen
Any drug which causes the onset of an allergic reaction.
Application(s): antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sulfamethazine (CHEBI:102265) has functional parent sulfanilamide (CHEBI:45373)
sulfamethazine (CHEBI:102265) has role antibacterial drug (CHEBI:36047)
sulfamethazine (CHEBI:102265) has role antiinfective agent (CHEBI:35441)
sulfamethazine (CHEBI:102265) has role antimicrobial agent (CHEBI:33281)
sulfamethazine (CHEBI:102265) has role carcinogenic agent (CHEBI:50903)
sulfamethazine (CHEBI:102265) has role drug allergen (CHEBI:88188)
sulfamethazine (CHEBI:102265) has role EC (dihydropteroate synthase) inhibitor (CHEBI:50502)
sulfamethazine (CHEBI:102265) has role environmental contaminant (CHEBI:78298)
sulfamethazine (CHEBI:102265) has role ligand (CHEBI:52214)
sulfamethazine (CHEBI:102265) has role xenobiotic (CHEBI:35703)
sulfamethazine (CHEBI:102265) is a pyrimidines (CHEBI:39447)
sulfamethazine (CHEBI:102265) is a sulfonamide (CHEBI:35358)
sulfamethazine (CHEBI:102265) is a sulfonamide antibiotic (CHEBI:87228)
Incoming sulfabromomethazine (CHEBI:145405) has functional parent sulfamethazine (CHEBI:102265)
INNs Sources
sulfadimidina ChemIDplus
sulfadimidine KEGG DRUG
sulfadimidinum ChemIDplus
Synonyms Sources
(p-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin ChEBI
2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine NIST Chemistry WebBook
2-(p-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine ChemIDplus
2-Sulfanilamido-4,6-dimethylpyrimidine ChemIDplus
4,6-Dimethyl-2-sulfanilamidopyrimidine ChemIDplus
4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide ChemIDplus
4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide ChEMBL
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide ChEMBL
6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidin ChemIDplus
N-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide NIST Chemistry WebBook
N1-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide NIST Chemistry WebBook
N1-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide NIST Chemistry WebBook
Sulfadimethyldiazine ChemIDplus
Sulfadimethylpyrimidine ChemIDplus
Sulfametazina ChemIDplus
Sulfametazyny ChemIDplus
sulfamethazone ChEBI
Sulfamezathine ChemIDplus
Sulphadimethylpyrimidine ChemIDplus
Sulphamethazine ChemIDplus
Manual Xrefs Databases
1829 VSDB
2502 DrugCentral
DB01582 DrugBank
EP1861101 Patent
GB546158 Patent
GB552887 Patent
HMDB0015522 HMDB
Sulfadimidine Wikipedia
US2407966 Patent
US3119818 Patent
WO2005016386 Patent
View more database links
Registry Numbers Types Sources
1009759 Gmelin Registry Number Gmelin
261304 Beilstein Registry Number Beilstein
261304 Reaxys Registry Number Reaxys
57-68-1 CAS Registry Number KEGG COMPOUND
57-68-1 CAS Registry Number ChemIDplus
57-68-1 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11431418 PubMed citation Europe PMC
14552772 PubMed citation ChEMBL
15603963 PubMed citation ChEMBL
17311370 PubMed citation ChEMBL
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20028131 PubMed citation Europe PMC
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23636590 PubMed citation Europe PMC
23673752 PubMed citation Europe PMC
23673946 PubMed citation Europe PMC
23704574 PubMed citation Europe PMC
6864729 PubMed citation ChEMBL
7021831 PubMed citation ChEMBL
7328159 PubMed citation Europe PMC
8199304 PubMed citation Europe PMC
9886437 PubMed citation Europe PMC
Last Modified
18 November 2019
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag