Rofecoxib (CHEM016866)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:45:52 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016866
Identification
Common NameRofecoxib
ClassSmall Molecule
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.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Phenyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanoneChEBI
4-[4-(Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanoneChEBI
CeoxxChEBI
RofecoxibumChEBI
VioxxChEBI
3-Phenyl-4-[4-(methylsulphonyl)phenyl]-2(5H)-furanoneGenerator
4-[4-(Methylsulphonyl)phenyl]-3-phenyl-2(5H)-furanoneGenerator
Merck frosst brand OF rofecoxibMeSH
Merck sharp and dhome brand OF rofecoxibMeSH
RefecoxibMeSH
Merck brand OF rofecoxibMeSH
Cahill may roberts brand OF rofecoxibMeSH
MSD Brand OF rofecoxibMeSH
Vioxx dolorMeSH
Chemical FormulaC17H14O4S
Average Molecular Mass314.356 g/mol
Monoisotopic Mass314.061 g/mol
CAS Registry Number162011-90-7
IUPAC Name4-(4-methanesulfonylphenyl)-3-phenyl-2,5-dihydrofuran-2-one
Traditional Namerofecoxib
SMILESCS(=O)(=O)C1=CC=C(C=C1)C1=C(C(=O)OC1)C1=CC=CC=C1
InChI IdentifierInChI=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
InChI KeyRZJQGNCSTQAWON-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Benzenesulfonyl group
  • Monocyclic benzene moiety
  • 2-furanone
  • Benzenoid
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Sulfonyl
  • Sulfone
  • Carboxylic acid ester
  • Lactone
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP2.32ALOGPS
logP2.56ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.84ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.08 m³·mol⁻¹ChemAxon
Polarizability31.74 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0601-0390000000-d4d8a8654a5376343cabSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0497000000-44320e93d610fb5074f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0496000000-06716b4dad8f8d33dee6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-2920000000-abe97627fbae89daa0dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0497000000-44320e93d610fb5074f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0300900000-8c21a5272c47622769e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0390000000-b69da0c82250f1f81243Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0496000000-06716b4dad8f8d33dee6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2920000000-abe97627fbae89daa0dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1129000000-9b4f4aec83cb3607f04cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0400-9288000000-c849d26e51ffb578eff6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9320000000-204a39f3b3ba2ec76d4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-4ef39ddbe094b85ea63eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1798000000-e6d03de8c00b576e795cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-5950000000-4dfc8f0e1edbfb7b74ddSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00533
HMDB IDHMDB0061179
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRofecoxib
Chemspider IDNot Available
ChEBI ID8887
PubChem Compound ID5090
Kegg Compound IDC07590
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10859630
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11014111
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12069696
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16934051
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20162413
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217