CHEBI:73044 - lumiracoxib

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ChEBI Name lumiracoxib
ChEBI ID CHEBI:73044
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 A highly selective cyclooxygenase 2 inhibitor, it was briefly used for the treatment of osteoarthritis, but was withdrawn due to concersns of hepatotoxicity.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 293.062
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)
InChIKey KHPKQFYUPIUARC-UHFFFAOYSA-N
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)
IUPAC Name
{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
D03714 KEGG DRUG
DB01283 DrugBank
HMDB0015403 HMDB
Lumiracoxib Wikipedia
LUR PDBeChem
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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
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17380211 PubMed citation Europe PMC
19800190 PubMed citation Europe PMC
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Last Modified
22 February 2017