rofecoxib (CHEBI:8887)

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ChEBI Name	rofecoxib

ChEBI ID	CHEBI:8887

Definition	A 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 A selective cyclooxygenase 2 inhibitor, it was used from 1999 to 2004 for the treatment of ostoarthritis, but was withdrawn following concerns about an associated increased risk of heart attack and stroke.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C17H14O4S

Net Charge

Average Mass

314.35600

Monoisotopic Mass

314.06128

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.

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

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

Last Modified

19 June 2017