CEL

4-[5-(4-METHYLPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL]BENZENESULFONAMIDE

Created: 2003-03-20
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count0
Bond Count42
Aromatic Bond Count19
2D diagram of CEL

Chemical Component Summary

Name4-[5-(4-METHYLPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL]BENZENESULFONAMIDE
SynonymsCELECOXIB
Systematic Name (OpenEye OEToolkits)4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
FormulaC17 H14 F3 N3 O2 S
Molecular Weight381.372
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=S(=O)(c3ccc(n1nc(cc1c2ccc(cc2)C)C(F)(F)F)cc3)N
SMILESCACTVS3.341Cc1ccc(cc1)c2cc(nn2c3ccc(cc3)[S](N)(=O)=O)C(F)(F)F
SMILESOpenEye OEToolkits1.5.0Cc1ccc(cc1)c2cc(nn2c3ccc(cc3)S(=O)(=O)N)C(F)(F)F
Canonical SMILESCACTVS3.341 Cc1ccc(cc1)c2cc(nn2c3ccc(cc3)[S](N)(=O)=O)C(F)(F)F
Canonical SMILESOpenEye OEToolkits1.5.0 Cc1ccc(cc1)c2cc(nn2c3ccc(cc3)S(=O)(=O)N)C(F)(F)F
InChIInChI1.03 InChI=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)
InChIKeyInChI1.03 RZEKVGVHFLEQIL-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00482 
NameCelecoxib
Groups
  • approved
  • investigational
DescriptionCelecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is a nonsteroidal anti-inflammatory drug (NSAID) which is known for its decreased risk of causing gastrointestinal bleeding compared to other NSAIDS.[A181544] It is used to manage symptoms of various types of arthritis pain and in familial adenomatous polyposis (FAP) to reduce precancerous polyps in the colon.[A181532] It is marketed by Pfizer under the brand name Celebrex, and was initially granted FDA approval in 1998.[L7604] Interestingly, selective COX-2 inhibitors (especially celecoxib), have been evaluated as potential cancer chemopreventive and therapeutic drugs in clinical trials for a variety of malignancies.[A34124]
Synonyms
  • Celecoxib
  • Célécoxib
  • p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide
  • Celecoxibum
Brand Names
  • Consensi
  • Celecoxib 50 mg
  • Dom-celecoxib
  • Celebrex
  • Nra-celecoxib
IndicationCelecoxib is indicated for symptomatic treatment of adult osteoarthritis (OA) and adult rheumatoid arthritis (RA).[L7646] Celecoxib is not a substitute for aspirin for cardiovascular event prophylaxis.[L7646] It may be also be used to treat acute pain from various sources, juvenile rheumatoid arthritis in children over 2, ankylosing spondylitis, and primary dysmenorrhea.[L7646] Celecoxib, in combination with [tramadol], is indicated for the management of acute pain in adults severe enough to require an opioid analgesic and in whom alternative treatments are inadequate.[L38949]
Categories
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Amides
  • Analgesics
  • Analgesics, Non-Narcotic
ATC-Code
  • N02AJ16
  • M01AH01
  • G01AE10
  • L01XX33
  • C08CA51
CAS number169590-42-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Carbonic anhydrase 2MSHHWGYGKHNGPEHWHKDFPIAKGERQSPVDIDTHTAKYDPSLKPLSVS...unknowninhibitor
Carbonic anhydrase 3MAKEWGYASHNGPDHWHELFPNAKGENQSPVELHTKDIRHDPSLQPWSVS...unknowninhibitor
Cadherin-11MKENYCLQAALVCLGMLCHSHAFAPERRGHLRPSFHGHHEKGKEGQVLQR...unknowninhibitor
3-phosphoinositide-dependent protein kinase 1MARTTSQLYDAVPIQSSVVLCSCPSPSMVRTQTESSTPPGIPGGSRQGPA...unknowninhibitor
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 CHEMBL118
PubChem 2662
ChEMBL CHEMBL118
ChEBI CHEBI:41423
CCDC/CSD LIQPUY, DIBBUL02, DIBBUL01, VIGDAR01, NOKZEV, NOKZOF, LIQQEJ, LIQQIN, POVGUE, CUZVIE, POVGAK, NOKZUL, LIQQIN01, POVGEO, POVGIS, POVHEP, POVGOY, POVHAL, NOKZIZ, LIQQAF, POVHOZ, POVHIT, LIQQIN02, DIBBUL
COD 4002956, 7214110, 1551854, 1551856, 7214112, 7214113, 7218363, 7218359, 1551857, 7214114, 7218360, 7218365, 7218362, 1551855, 7214111, 7218366, 7214115, 2009313