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CHEBI:8887 - rofecoxib

Default Structure
ChEBI IDCHEBI:8887
ChEBI Namerofecoxib
Stars
DefinitionA butenolide that is furan-2(5H)-one substituted by a phenyl group at position 3 and by a p-(methylsulfonyl)phenyl group at position 4. A selective cyclooxygenase 2 inhibitor, it was used from 1999 to 2004 for the treatment of ostoarthritis, but was withdrawn following concerns about an associated increased risk of heart attack and stroke.
Last Modified19 June 2017
DownloadsMolfile
FormulaC17H14O4S
Net Charge0
Average Mass314.362
Monoisotopic Mass314.06128
SMILESCS(=O)(=O)c1ccc(C2=C(c3ccccc3)C(=O)OC2)cc1
InChIInChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3
InChIKeyRZJQGNCSTQAWON-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Roles:
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 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
rofecoxib (CHEBI:8887) has role analgesic (CHEBI:35480)
rofecoxib (CHEBI:8887) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
rofecoxib (CHEBI:8887) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
rofecoxib (CHEBI:8887) is a butenolide (CHEBI:50523)
rofecoxib (CHEBI:8887) is a sulfone (CHEBI:35850)
IUPAC Name 
4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one
INNs  Source
rofecoxibWHO MedNet
rofecoxibWHO MedNet
rofécoxibWHO MedNet
rofecoxibumWHO MedNet
Synonyms  Source
3-phenyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanoneChemIDplus
4-[4-(methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanoneChemIDplus
CeoxxChemIDplus
RofecoxibKEGG COMPOUND
VioxxChemIDplus
Manual XrefsDatabases
2397DrugCentral
C07590KEGG COMPOUND
D00568KEGG DRUG
DB00533DrugBank
LSM-2482LINCS
RofecoxibWikipedia
Registry NumbersSources
Reaxys:8269007Reaxys
CAS:162011-90-7ChemIDplus
CAS:162011-90-7KEGG COMPOUND
Citations