Chemical Component Summary

NameRofecoxib
SynonymsVioxx
Identifiers3-(4-methylsulfonylphenyl)-4-phenyl-2~{H}-furan-5-one
FormulaC17 H14 O4 S
Molecular Weight314.356
TypeNON-POLYMER
Isomeric SMILESCS(=O)(=O)c1ccc(cc1)C2=C(C(=O)OC2)c3ccccc3
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

Chemical Details

Formal Charge0
Atom Count36
Chiral Atom Count0
Bond Count38
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB00533 
NameRofecoxib
Groups
  • approved
  • investigational
  • withdrawn
DescriptionRofecoxib is used for the treatment of osteoarthritis, rheumatoid arthritis, acute pain in adults, and primary dysmenorrhea, as well as acute treatment of migraine attacks with or without auras. Rofecoxib is a solid. This compound belongs to the stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Rofecoxib has a half-life of 17 hours and its mean oral bioavailability at therapeutically recommended doses of 125, 25, and 50 mg is approximately 93%. The proteins that rofecoxib target include elastin and prostaglandin G/H synthase 2. Cytochrome P450 1A2, Cytochrome P450 3A4, Cytochrome P450 2C9, Cytochrome P450 2C8, and Prostaglandin G/H synthase 1 are known to metabolize rofecoxib. On September 30, 2004, Merck voluntarily withdrew rofecoxib from the market because of concerns about increased risk of heart attack and stroke associated with long-term, high-dosage use.
Synonyms
  • 3-phenyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone
  • 4-[4-(methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone
  • Rofécoxib
  • Rofecoxibum
  • Rofecoxib
Brand Names
  • Vioxx Tab 12.5mg
  • Vioxx Suspension 12.5mg/5ml
  • Vioxx Tab 25mg
IndicationFor the treatment of osteoarthritis, rheumatoid arthritis, acute pain in adults, and primary dysmenorrhea, as well as acute treatment of migraine attacks with or without auras.
Categories
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
ATC-CodeM01AH02
CAS number162011-90-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
ElastinMAGLTAAAPRPGVLLLLLSILHPSRPGGVPGAIPGGVPGGVFYPGAGLGA...unknownother/unknown
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknownsubstrate
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknowninhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL122
PubChem 5090
ChEMBL CHEMBL122
ChEBI CHEBI:8887
CCDC/CSD CAXMUJ
COD 2010656