1.02011-09-21 00:32:00 UTC2018-05-28 18:36:46 UTCFDB023586CelecoxibCelecoxib (INN) is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer under the brand name Celebrex. In some countries, it is branded Celebra.; Celecoxib is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis.
Celecoxib is a highly selective COX-2 inhibitor and primarily inhibits this isoform of cyclooxygenase, whereas traditional NSAIDs inhibit both COX-1 and COX-2. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. In theory, this specificity allows celecoxib and other COX-2 inhibitors to reduce inflammation (and pain) while minimizing gastrointestinal adverse drug reactions (e.g. stomach ulcers) that are common with non-selective NSAIDs. It also means that it has a reduced effect on platelet aggregation compared to traditional NSAIDs; Celecoxib is a highly selective COX-2 inhibitor and primarily inhibits this isoform of cyclooxygenase, whereas traditional NSAIDs inhibit both COX-1 and COX-2. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. In theory, this specificity allows celecoxib and other COX-2 inhibitors to reduce inflammation (and pain) while minimizing gastrointestinal adverse drug reactions (e.g. stomach ulcers) that are common with non-selective NSAIDs. It also means that it has a reduced effect on platelet aggregation compared to traditional NSAIDs. [HMDB]CelebrexCelecoxibCelecoxibumCelocoxibP-(5-P-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamideP-(5-P-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulphonamideC17H14F3N3O2S381.372381.0758820124-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamidecelecoxib169590-42-5CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)FInChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)RZEKVGVHFLEQIL-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.PhenylpyrazolesOrganic compoundsOrganoheterocyclic compoundsAzolesPyrazolesAromatic heteromonocyclic compoundsAlkyl fluoridesAminosulfonyl compoundsAzacyclic compoundsBenzenesulfonamidesBenzenesulfonyl compoundsHeteroaromatic compoundsHydrocarbon derivativesOrganic oxidesOrganofluoridesOrganonitrogen compoundsOrganopnictogen compoundsOrganosulfonamidesToluenesAlkyl fluorideAlkyl halideAminosulfonyl compoundAromatic heteromonocyclic compoundAzacycleBenzenesulfonamideBenzenesulfonyl groupBenzenoidHeteroaromatic compoundHydrocarbon derivativeMonocyclic benzene moietyOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic sulfonic acid or derivativesOrganofluorideOrganohalogen compoundOrganonitrogen compoundOrganopnictogen compoundOrganosulfonic acid amideOrganosulfonic acid or derivativesOrganosulfur compoundPhenylpyrazoleSulfonylTolueneorganofluorine compoundpyrazolessulfonamideSolidlogp3.99logs-4.88solubility5.03e-03 g/llogp4.01pka_strongest_acidic10.7pka_strongest_basic-0.42iupac4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamideaverage_mass381.372mono_mass381.075882012smilesCC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)FformulaC17H14F3N3O2SinchiInChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)inchikeyRZEKVGVHFLEQIL-UHFFFAOYSA-Npolar_surface_area77.98refractivity92.23polarizability35.2rotatable_bond_count4acceptor_count3donor_count1physiological_charge0formal_charge0Specdb::CMs11642Specdb::CMs137707Specdb::CMs145441Specdb::MsMs99063Specdb::MsMs99064Specdb::MsMs99065Specdb::MsMs164142Specdb::MsMs164143Specdb::MsMs164144Specdb::MsMs374709Specdb::MsMs440604Specdb::MsMs450610Specdb::MsMs451359Specdb::MsMs452358Specdb::MsMs2236026Specdb::MsMs2236062Specdb::MsMs2237340Specdb::MsMs2237378Specdb::MsMs2238074Specdb::MsMs2238188Specdb::MsMs2239373Specdb::MsMs2239481Specdb::MsMs2240336Specdb::MsMs2241387Specdb::MsMs2242364Specdb::MsMs2243478Specdb::MsMs2244490Specdb::MsMs2245600HMDB050143520CEL3-phosphoinositide-dependent protein kinase 1O15530PDPK1