CHEBI:8249 - piroxicam

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ChEBI Name piroxicam
ChEBI ID CHEBI:8249
Definition A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide with the exocyclic nitrogen of 2-aminopyridine. A non-steroidal anti-inflammatory drug of the oxicam class, it is used to relieve pain and works by preventing the production of endogenous prostaglandins involved in the mediation of pain, stiffness, tenderness and swelling.
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Formula C15H13N3O4S
Net Charge 0
Average Mass 331.34600
Monoisotopic Mass 331.063
InChI InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
InChIKey QYSPLQLAKJAUJT-UHFFFAOYSA-N
SMILES CN1C(C(=O)Nc2ccccn2)=C(O)c2ccccc2S1(=O)=O
Roles Classification
Biological Role(s): EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via benzothiazine )
Application(s): antirheumatic drug
A drug used to treat rheumatoid arthritis.
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.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
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ChEBI Ontology
Outgoing piroxicam (CHEBI:8249) has role analgesic (CHEBI:35480)
piroxicam (CHEBI:8249) has role antirheumatic drug (CHEBI:35842)
piroxicam (CHEBI:8249) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
piroxicam (CHEBI:8249) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
piroxicam (CHEBI:8249) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
piroxicam (CHEBI:8249) is a benzothiazine (CHEBI:46899)
piroxicam (CHEBI:8249) is a monocarboxylic acid amide (CHEBI:29347)
piroxicam (CHEBI:8249) is a pyridines (CHEBI:26421)
Incoming ampiroxicam (CHEBI:31210) has functional parent piroxicam (CHEBI:8249)
droxicam (CHEBI:76133) has functional parent piroxicam (CHEBI:8249)
IUPAC Name
4-hydroxy-2-methyl-N-pyridin-2-yl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
INNs Sources
piroxicam WHO MedNet
piroxicamum ChemIDplus
Synonyms Sources
4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid ChemIDplus
Piroxicam KEGG COMPOUND
Pyroxycam ChemIDplus
Brand Names Sources
Feldene DrugBank
FELDENE KEGG DRUG
Database Links Databases
2210 DrugCentral
C01608 KEGG COMPOUND
D00127 KEGG DRUG
DB00554 DrugBank
DE1943265 Patent
HMDB0014694 HMDB
Piroxicam Wikipedia
US3591584 Patent
View more database links
Registry Numbers Types Sources
36322-90-4 CAS Registry Number NIST Chemistry WebBook
36322-90-4 CAS Registry Number ChemIDplus
627692 Beilstein Registry Number Beilstein
627692 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11142413 PubMed citation Europe PMC
12154043 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
Last Modified
19 June 2017