CHEBI:73044 - lumiracoxib

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ChEBI Name lumiracoxib
Definition An amino acid that is phenylacetic acid which is substituted at position 2 by the nitrogen of 2-chloro-6-fluoroaniline and at position 5 by a methyl group. A highly selective cyclooxygenase 2 inhibitor, it was briefly used for the treatment of osteoarthritis, but was withdrawn due to concersns of hepatotoxicity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H13ClFNO2
Net Charge 0
Average Mass 293.72100
Monoisotopic Mass 293.06188
InChI InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)
SMILES Cc1ccc(Nc2c(F)cccc2Cl)c(CC(O)=O)c1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
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.
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ChEBI Ontology
Outgoing lumiracoxib (CHEBI:73044) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
lumiracoxib (CHEBI:73044) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
lumiracoxib (CHEBI:73044) is a amino acid (CHEBI:33709)
lumiracoxib (CHEBI:73044) is a monocarboxylic acid (CHEBI:25384)
lumiracoxib (CHEBI:73044) is a organochlorine compound (CHEBI:36683)
lumiracoxib (CHEBI:73044) is a organofluorine compound (CHEBI:37143)
lumiracoxib (CHEBI:73044) is a secondary amino compound (CHEBI:50995)
{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid
INNs Sources
lumiracoxib WHO MedNet
lumiracoxib WHO MedNet
lumiracoxib WHO MedNet
lumiracoxibum WHO MedNet
Synonyms Sources
2-((2-chloro-6-fluorophenyl)amino)-5-methylbenzeneacetic acid ChemIDplus
COX 189 ChemIDplus
COX-189 ChemIDplus
COX189 ChemIDplus
Brand Name Source
Prexige ChemIDplus
Manual Xrefs Databases
1618 DrugCentral
DB01283 DrugBank
HMDB0015403 HMDB
Lumiracoxib Wikipedia
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Registry Numbers Types Sources
220991-20-8 CAS Registry Number KEGG DRUG
220991-20-8 CAS Registry Number ChemIDplus
9784107 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14965322 PubMed citation Europe PMC
15311562 PubMed citation Europe PMC
15456339 PubMed citation Europe PMC
17380211 PubMed citation Europe PMC
19800190 PubMed citation Europe PMC
21688392 PubMed citation Europe PMC
22069133 PubMed citation Europe PMC
22142375 PubMed citation Europe PMC
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Last Modified
22 February 2017