CHEBI:9332 - sulfamethoxazole

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ChEBI Name sulfamethoxazole
ChEBI ID CHEBI:9332
Definition An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:102247
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Formula C10H11N3O3S
Net Charge 0
Average Mass 253.279
Monoisotopic Mass 253.052
InChI InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChIKey JLKIGFTWXXRPMT-UHFFFAOYSA-N
SMILES C=1(C=CC(=CC1)N)S(NC=2C=C(ON2)C)(=O)=O
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
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.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via sulfonamide antibiotic )
drug allergen
Any drug which causes the onset of an allergic reaction.
P450 inhibitor
An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
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.
antibacterial agent
A substance that kills or slows the growth of bacteria.
xenobiotic
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.
Application(s): drug allergen
Any drug which causes the onset of an allergic reaction.
antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sulfamethoxazole (CHEBI:9332) has functional parent sulfanilamide (CHEBI:45373)
sulfamethoxazole (CHEBI:9332) has role antibacterial agent (CHEBI:33282)
sulfamethoxazole (CHEBI:9332) has role antiinfective agent (CHEBI:35441)
sulfamethoxazole (CHEBI:9332) has role antimicrobial agent (CHEBI:33281)
sulfamethoxazole (CHEBI:9332) has role drug allergen (CHEBI:88188)
sulfamethoxazole (CHEBI:9332) has role EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor (CHEBI:74234)
sulfamethoxazole (CHEBI:9332) has role EC 2.5.1.15 (dihydropteroate synthase) inhibitor (CHEBI:50502)
sulfamethoxazole (CHEBI:9332) has role environmental contaminant (CHEBI:78298)
sulfamethoxazole (CHEBI:9332) has role epitope (CHEBI:53000)
sulfamethoxazole (CHEBI:9332) has role P450 inhibitor (CHEBI:50183)
sulfamethoxazole (CHEBI:9332) has role xenobiotic (CHEBI:35703)
sulfamethoxazole (CHEBI:9332) is a isoxazoles (CHEBI:55373)
sulfamethoxazole (CHEBI:9332) is a substituted aniline (CHEBI:48975)
sulfamethoxazole (CHEBI:9332) is a sulfonamide (CHEBI:35358)
sulfamethoxazole (CHEBI:9332) is a sulfonamide antibiotic (CHEBI:87228)
Incoming N-acetylsulfamethoxazole (CHEBI:31169) has functional parent sulfamethoxazole (CHEBI:9332)
nitrososulfamethoxazole (CHEBI:53017) has functional parent sulfamethoxazole (CHEBI:9332)
sulfamethoxazole hydroxylamine (CHEBI:53016) has functional parent sulfamethoxazole (CHEBI:9332)
co-trimoxazole (CHEBI:3770) has part sulfamethoxazole (CHEBI:9332)
IUPAC Name
4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
Synonyms Sources
3-(p-Aminophenylsulfonamido)-5-methylisoxazole ChemIDplus
3-Sulfanilamido-5-methylisoxazole ChemIDplus
4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide ChemIDplus
Gantanol (TN) KEGG DRUG
SMX ChEBI
Sulfamethoxazole KEGG COMPOUND
sulphamethoxazole ChEBI
Database Links Databases
2514 DrugCentral
C07315 KEGG COMPOUND
D00447 KEGG DRUG
DB01015 DrugBank
HMDB0015150 HMDB
LSM-5422 LINCS
Sulfamethoxazole Wikipedia
View more database links
Registry Numbers Types Sources
226453 Reaxys Registry Number Reaxys
226453 Gmelin Registry Number Gmelin
723-46-6 CAS Registry Number ChemIDplus
723-46-6 CAS Registry Number DrugBank
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag