CHEBI:31210 - ampiroxicam

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ChEBI Name ampiroxicam
ChEBI ID CHEBI:31210
Definition A benzothiazine that is the 1-[(ethoxycarbonyl)oxy]ethyl ether of piroxicam. A prodrug for piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H21N3O7S
Net Charge 0
Average Mass 447.46200
Monoisotopic Mass 447.110
InChI InChI=1S/C20H21N3O7S/c1-4-28-20(25)30-13(2)29-18-14-9-5-6-10-15(14)31(26,27)23(3)17(18)19(24)22-16-11-7-8-12-21-16/h5-13H,4H2,1-3H3,(H,21,22,24)
InChIKey LSNWBKACGXCGAJ-UHFFFAOYSA-N
SMILES CCOC(=O)OC(C)OC1=C(N(C)S(=O)(=O)c2ccccc12)C(=O)Nc1ccccn1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
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.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via benzothiazine )
Application(s): 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.
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.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ampiroxicam (CHEBI:31210) has functional parent piroxicam (CHEBI:8249)
ampiroxicam (CHEBI:31210) has role analgesic (CHEBI:35480)
ampiroxicam (CHEBI:31210) has role antirheumatic drug (CHEBI:35842)
ampiroxicam (CHEBI:31210) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
ampiroxicam (CHEBI:31210) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
ampiroxicam (CHEBI:31210) has role prodrug (CHEBI:50266)
ampiroxicam (CHEBI:31210) is a acetal (CHEBI:59769)
ampiroxicam (CHEBI:31210) is a aminopyridine (CHEBI:38207)
ampiroxicam (CHEBI:31210) is a benzothiazine (CHEBI:46899)
ampiroxicam (CHEBI:31210) is a etabonate ester (CHEBI:50850)
ampiroxicam (CHEBI:31210) is a monocarboxylic acid amide (CHEBI:29347)
ampiroxicam (CHEBI:31210) is a sulfonamide (CHEBI:35358)
IUPAC Name
ethyl 1-{[2-methyl-1,1-dioxido-3-(pyridin-2-ylcarbamoyl)-2H-1,2-benzothiazin-4-yl]oxy}ethyl carbonate
INNs Sources
ampiroxicam WHO MedNet
ampiroxicam WHO MedNet
ampiroxicam ChemIDplus
ampiroxicamum ChemIDplus
Synonyms Sources
carbonic acid ethyl 1-({2-methyl-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl}oxy)ethyl ester S,S-dioxide ChemIDplus
CP 65703 ChemIDplus
CP-65703 ChemIDplus
Brand Name Source
Flucam KEGG DRUG
Manual Xrefs Databases
199 DrugCentral
Ampiroxicam Wikipedia
D01397 KEGG DRUG
EP147177 Patent
LSM-5043 LINCS
US4551452 Patent
View more database links
Registry Numbers Types Sources
5184713 Reaxys Registry Number Reaxys
99464-64-9 CAS Registry Number ChemIDplus
99464-64-9 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
10527378 PubMed citation Europe PMC
11469844 PubMed citation Europe PMC
2219958 PubMed citation Europe PMC
8304243 PubMed citation Europe PMC
8730175 PubMed citation Europe PMC
9529571 PubMed citation Europe PMC
Last Modified
22 February 2017