isoxicam (CHEBI:76163)

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ChEBI Name	isoxicam

ChEBI ID	CHEBI:76163

Definition	A monocarboxylic acid amide that is piroxicam in which the pyrid-2-yl group is replaced by a 5-methyl-1,2-oxazol-3-yl group. A non-steroidal anti-inflammatory drug, it was withdrawn from the market in the 1980s following its association with cases of Stevens-Johnson syndrome.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C14H13N3O5S

Net Charge

Average Mass

335.33500

Monoisotopic Mass

335.05759

InChI

InChI=1S/C14H13N3O5S/c1-8-7-11(16-22-8)15-14(19)12-13(18)9-5-3-4-6-10(9)23(20,21)17(12)2/h3-7,18H,1-2H3,(H,15,16,19)

InChIKey

YYUAYBYLJSNDCX-UHFFFAOYSA-N

SMILES

CN1C(C(=O)Nc2cc(C)on2)=C(O)c2ccccc2S1(=O)=O

Roles Classification
Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via benzothiazine )

Application(s):	non-steroidal anti-inflammatory drug An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. antirheumatic drug A drug used to treat rheumatoid arthritis.

ChEBI Ontology
Outgoing	isoxicam (CHEBI:76163) has role antirheumatic drug (CHEBI:35842) isoxicam (CHEBI:76163) has role non-steroidal anti-inflammatory drug (CHEBI:35475) isoxicam (CHEBI:76163) is a benzothiazine (CHEBI:46899) isoxicam (CHEBI:76163) is a isoxazoles (CHEBI:55373) isoxicam (CHEBI:76163) is a monocarboxylic acid amide (CHEBI:29347)

IUPAC Name

4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Synonyms	Sources
4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide	ChemIDplus
4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide	ChEBI
BRN 0577221	ChemIDplus
EINECS 252-084-5	ChemIDplus
N-(5-methyl-3-isoxazolyl)-4-hydroxy-2-methyl-2H-1,2-benzthiazine-3-carboxamide 1,1-dioxide	ChEBI
UNII-8XU734C4NG	ChemIDplus
W 8495	ChemIDplus

Brand Name	Source
Maxicam	KEGG DRUG

Last Modified

22 February 2017