CHEBI:8887 - rofecoxib

Main ChEBI Ontology Automatic Xrefs
ChEBI Name rofecoxib
ChEBI ID CHEBI:8887
Definition A butenolide that is furan-2(5H)-one that is 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 A selective cyclooxygenase 2 inhibitor, it was used from 1999 to 2004 for the treatment of ostoarthritis, but was withdrawn following concerns about an associated increased risk of heart attack and stroke.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Save molfile Download Molfile
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C17H14O4S
Net Charge 0
Average Mass 314.35600
InChI InChI=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
InChIKey RZJQGNCSTQAWON-UHFFFAOYSA-N
SMILES CS(=O)(=O)c1ccc(cc1)C1=C(C(=O)OC1)c1ccccc1
Roles Classification
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
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.
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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
rofecoxib WHO MedNet
rofécoxib WHO MedNet
rofecoxib WHO MedNet
rofecoxibum WHO MedNet
Synonyms Sources
3-phenyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone ChemIDplus
4-[4-(methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone ChemIDplus
Ceoxx ChemIDplus
Rofecoxib KEGG COMPOUND
Vioxx ChemIDplus
Database Links Databases
C07590 KEGG COMPOUND
D00568 KEGG DRUG
DB00533 DrugBank
Rofecoxib Wikipedia
View more database links
Registry Numbers Types Sources
162011-90-7 CAS Registry Number KEGG COMPOUND
162011-90-7 CAS Registry Number ChemIDplus
8269007 Beilstein Registry Number Beilstein
8269007 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10859630 PubMed citation CiteXplore
11014111 PubMed citation CiteXplore
12069696 PubMed citation CiteXplore
16934051 PubMed citation CiteXplore
20162413 PubMed citation CiteXplore
Last Modified
27 March 2013