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Identification
NameCelecoxib
Accession NumberDB00482  (APRD00373)
TypeSmall Molecule
GroupsApproved, Investigational
Description

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. It is marketed by Pfizer under the brand name Celebrex. In some countries, it is branded Celebra. Celecoxib is available by prescription in capsule form.

Structure
Thumb
Synonyms
SynonymLanguageCode
CelebrexNot AvailableNot Available
CelecoxibGerman/SpanishINN
CélécoxibFrenchINN
CelecoxibumLatin INN
P-(5-P-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamideNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Celebrexcapsule50 mgoralG.D. Searle LLC Division of Pfizer Inc1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralG.D. Searle LLC Division of Pfizer Inc1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralG.D. Searle LLC Division of Pfizer Inc1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule400 mgoralG.D. Searle LLC Division of Pfizer Inc1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule50 mgoralMylan Pharmaceuticals Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule100 mgoralMylan Pharmaceuticals Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralMylan Pharmaceuticals Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule400 mgoralMylan Pharmaceuticals Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule50 mgoralActavis Pharma, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule100 mgoralActavis Pharma, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralActavis Pharma, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule400 mgoralActavis Pharma, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralSTAT Rx USA LLC1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralSTAT Rx USA LLC1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralRebel Distributors Corp.1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralRebel Distributors Corp.1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralAidarex Pharmaceuticals LLC1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralSTAT Rx USA LLC1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralSTAT Rx USA LLC1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralPd Rx Pharmaceuticals, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule100 mgoralPd Rx Pharmaceuticals, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralREMEDYREPACK INC.2013-06-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralREMEDYREPACK INC.2013-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralREMEDYREPACK INC.2013-12-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralREMEDYREPACK INC.2013-02-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralREMEDYREPACK INC.2013-05-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralREMEDYREPACK INC.2013-02-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralUnit Dose Services1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralUnit Dose Services1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralH.J. Harkins Company, Inc.1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralH.J. Harkins Company, Inc.1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralA S Medication Solutions Llc1999-01-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralA S Medication Solutions Llc1999-01-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralPhysicians Total Care, Inc.2000-05-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralPhysicians Total Care, Inc.1999-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule400 mgoralPhysicians Total Care, Inc.2006-01-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralCardinal Health1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralCardinal Health1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralCardinal Health1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralPd Rx Pharmaceuticals, Inc.1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralPd Rx Pharmaceuticals, Inc.1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralClinical Solutions Wholesale1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule50 mgoralGreenstone LLC2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule100 mgoralGreenstone LLC2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralGreenstone LLC2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule400 mgoralGreenstone LLC2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralDIRECT RX2014-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralProficient Rx LP1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralbryant ranch prepack1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralbryant ranch prepack1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule400 mgoralbryant ranch prepack1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralDispensing Solutions, Inc.1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralAphena Pharma Solutions Tennessee, Llc1998-10-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule50 mgoralLupin Pharmaceuticals, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule100 mgoralLupin Pharmaceuticals, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralLupin Pharmaceuticals, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule400 mgoralLupin Pharmaceuticals, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralKeltman Pharmaceuticals Inc.2006-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule200 mgoralPreferred Pharmaceuticals, Inc.2014-08-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralPreferred Pharmaceuticals, Inc.2014-12-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule100 mgoralPreferred Pharmaceuticals, Inc.2014-12-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celebrexcapsule100 mgoralPfizer Canada IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Celebrexcapsule200 mgoralPfizer Canada IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Celecoxibcapsule100 mgoralTeva Pharmaceuticals USA Inc2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralTeva Pharmaceuticals USA Inc2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule400 mgoralTeva Pharmaceuticals USA Inc2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule50 mgoralTeva Pharmaceuticals USA Inc2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule50 mgoralAv Kare, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule100 mgoralAv Kare, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralAv Kare, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule400 mgoralAv Kare, Inc.2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule200 mgoralSt. Mary's Medical Park Pharmacy2014-12-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Celecoxibcapsule100 mgoralPro Doc LimiteeNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Celecoxibcapsule200 mgoralPro Doc LimiteeNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Celecoxibcapsule100 mgoralSivem Pharmaceuticals UlcNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Celecoxibcapsule200 mgoralSivem Pharmaceuticals UlcNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Over the Counter ProductsNot Available
International Brands
NameCompany
ArticoxKeyfarm
ArticoxibNabiqasim
ArtiflexStandpharm
ArtilogPfizer
ArtixPharmalab
ArtrixibIntipharma
BlocktenInfarmasa
CaditarFarmindustria
CefinixFarmacoop
CelactSun
CelebraPfizer
OnsenalPfizer
ValdynePfizer
Brand mixtures
Brand NameIngredients
Caditar FlexCelecoxib and Orphenadrine
SaltsNot Available
CategoriesNot Available
CAS number169590-42-5
WeightAverage: 381.372
Monoisotopic: 381.075882012
Chemical FormulaC17H14F3N3O2S
InChI KeyRZEKVGVHFLEQIL-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
SMILES
CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Benzenesulfonamide
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azacycle
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor relief and management of osteoarthritis (OA), rheumatoid arthritis (RA), juvenile rheumatoid arthritis (JRA), ankylosing spondylitis, acute pain, primary dysmenorrhea and oral adjunct to usual care for patients with familial adenomatous polyposis
PharmacodynamicsCelecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). Celecoxib is used to treat rheumatoid arthritis, osteoarthritis, and familial adenomatous polyposis (FAP). Because of its lack of platelet effects, celecoxib is not a substitute for aspirin for cardiovascular prophylaxis. It is not known if there are any effects of celecoxib on platelets that may contribute to the increased risk of serious cardiovascular thrombotic adverse events associated with the use of celecoxib. Inhibition of PGE2 synthesis may lead to sodium and water retention through increased fluid reabsorption in the renal medullary thick ascending loop of Henle and perhaps other segments of the distal nephron. In the collecting ducts, PGE2 appears to inhibit water reabsorption by counteracting the action of antidiuretic hormone.
Mechanism of actionThe mechanism of action of celecoxib is believed to be due to inhibition of prostaglandin synthesis. Unlike most NSAIDs, which inhibit both types of cyclooxygenases (COX-1 and COX-2), celecoxib is a selective noncompetitive inhibitor of cyclooxygenase-2 (COX-2) enzyme. It binds with its polar sulfonamide side chain to a hydrophilic side pocket region close to the active COX-2 binding site. Both COX-1 and COX-2 catalyze the conversion of arachidonic acid to prostaglandin (PG) H2, the precursor of PGs and thromboxane.
AbsorptionWell absorbed in the gastrointestinal tract. When a single dose of 200 mg is given to healthy subjects, peak plasma levels occur 3 hours after an oral dose. The peak plasma level is 705 ng/mL. Absolute bioavailability studies have not been conducted. When multiple doses are given, steady-state is reached on or before Day 5. When taken with a high fat meal, peak plasma levels are delayed for about 1 to 2 hours with an increase in total absorption (AUC) of 10% to 20%.
Volume of distribution

Apparent volume of distribution at steady state (Vdss/F), 200 mg single dose, healthy subjects = 429 L

Protein binding97%, primarily to albumin and, to a lesser extent, a1-acid glycoprotein. Celecoxib is not preferentially bound to red blood cells.
Metabolism

Hepatic. Celecoxib metabolism is primarily mediated via cytochrome P450 2C9. Three metabolites, a primary alcohol, the corresponding carboxylic acid and its glucuronide conjugate, have been identified in human plasma. CYP3A4 is also involved in the hydroxylation of celecoxib but to a lesser extent. These metabolites are inactive as COX-1 or COX-2 inhibitors.

SubstrateEnzymesProduct
Celecoxib
HydroxycelecoxibDetails
Hydroxycelecoxib
CarboxycelecoxibDetails
Carboxycelecoxib
Celecoxib glucuronideDetails
Route of eliminationCelecoxib is eliminated predominantly by hepatic metabolism with little (<3%) unchanged drug recovered in the urine and feces. 57% of the oral dose is excreted in the feces and 27% is excreted into the urine. The primary metabolite in urine and feces was the carboxylic acid metabolite (73%). The amount of glucuronide in the urine is low.
Half lifeThe effective half-life is approximately 11 hours when a single 200 mg dose is given to healthy subjects. Terminal half-life is generally variable because of the low solubility of the drug thus prolonging absorption.
Clearance

Apparent clearance (CL/F), single oral 200 mg dose, healthy subjects = 27.7 L/hr.

ToxicitySymptoms of overdose include breathing difficulties, coma, drowsiness, gastrointestinal bleeding, high blood pressure, kidney failure, nausea, sluggishness, stomach pain, and vomiting.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Celecoxib Metabolism PathwayDrug metabolismSMP00644
Celecoxib Action PathwayDrug actionSMP00096
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2C9
Gene symbol: CYP2C9
UniProt: P11712
rs1057910 CYP2C9*1C AllelePoor drug metabolizer, lower dose requirements12893985
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9713
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.9287
P-glycoprotein inhibitor INon-inhibitor0.8619
P-glycoprotein inhibitor IINon-inhibitor0.792
Renal organic cation transporterNon-inhibitor0.8582
CYP450 2C9 substrateNon-substrate0.6237
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.5751
CYP450 1A2 substrateInhibitor0.7805
CYP450 2C9 substrateInhibitor0.6172
CYP450 2D6 substrateNon-inhibitor0.8594
CYP450 2C19 substrateInhibitor0.7169
CYP450 3A4 substrateInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7392
Ames testNon AMES toxic0.7185
CarcinogenicityNon-carcinogens0.7905
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3719 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9856
hERG inhibition (predictor II)Non-inhibitor0.8419
Pharmacoeconomics
Manufacturers
  • Gd searle llc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral100 mg
Capsuleoral200 mg
Capsuleoral400 mg
Capsuleoral50 mg
Prices
Unit descriptionCostUnit
Celebrex 400 mg capsule6.78USD capsule
Celebrex 200 mg capsule4.52USD capsule
Celebrex 100 mg capsule2.75USD capsule
Celebrex 50 mg capsule1.26USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada21775761999-10-262014-11-14
Canada22671862002-05-142017-10-14
United States54668231993-11-302013-11-30
United States59729861998-04-142018-04-14
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point158 °CPhysProp
water solubilityVery low water solubility (3.3 mg/L)Not Available
logP3.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00503 mg/mLALOGPS
logP3.99ALOGPS
logP4.01ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)10.7ChemAxon
pKa (Strongest Basic)-0.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.98 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.23 m3·mol-1ChemAxon
Polarizability35.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US5466823
General Reference
  1. Malhotra S, Shafiq N, Pandhi P: COX-2 inhibitors: a CLASS act or Just VIGORously promoted. MedGenMed. 2004 Mar 23;6(1):6. Pubmed
  2. Silverstein FE, Faich G, Goldstein JL, Simon LS, Pincus T, Whelton A, Makuch R, Eisen G, Agrawal NM, Stenson WF, Burr AM, Zhao WW, Kent JD, Lefkowith JB, Verburg KM, Geis GS: Gastrointestinal toxicity with celecoxib vs nonsteroidal anti-inflammatory drugs for osteoarthritis and rheumatoid arthritis: the CLASS study: A randomized controlled trial. Celecoxib Long-term Arthritis Safety Study. JAMA. 2000 Sep 13;284(10):1247-55. Pubmed
  3. Solomon SD, McMurray JJ, Pfeffer MA, Wittes J, Fowler R, Finn P, Anderson WF, Zauber A, Hawk E, Bertagnolli M: Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention. N Engl J Med. 2005 Mar 17;352(11):1071-80. Epub 2005 Feb 15. Pubmed
  4. Yelland MJ, Nikles CJ, McNairn N, Del Mar CB, Schluter PJ, Brown RM: Celecoxib compared with sustained-release paracetamol for osteoarthritis: a series of n-of-1 trials. Rheumatology (Oxford). 2007 Jan;46(1):135-40. Epub 2006 Jun 15. Pubmed
  5. Bertagnolli MM, Eagle CJ, Zauber AG, Redston M, Solomon SD, Kim K, Tang J, Rosenstein RB, Wittes J, Corle D, Hess TM, Woloj GM, Boisserie F, Anderson WF, Viner JL, Bagheri D, Burn J, Chung DC, Dewar T, Foley TR, Hoffman N, Macrae F, Pruitt RE, Saltzman JR, Salzberg B, Sylwestrowicz T, Gordon GB, Hawk ET: Celecoxib for the prevention of sporadic colorectal adenomas. N Engl J Med. 2006 Aug 31;355(9):873-84. Pubmed
  6. FDA label
  7. Sandberg M, Yasar U, Stromberg P, Hoog JO, Eliasson E: Oxidation of celecoxib by polymorphic cytochrome P450 2C9 and alcohol dehydrogenase. Br J Clin Pharmacol. 2002 Oct;54(4):423-9. Pubmed
External Links
ATC CodesL01XX33M01AH01
AHFS Codes
  • 28:08.04.08
PDB EntriesNot Available
FDA labelDownload (174 KB)
MSDSDownload (102 KB)
Interactions
Drug Interactions
Drug
AbciximabNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
AcenocoumarolNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
AliskirenNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of Aliskiren. Nonsteroidal Anti-Inflammatory Agents may enhance the nephrotoxic effect of Aliskiren.
AmikacinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
ArbekacinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
AripiprazoleCYP2D6 Inhibitors (Moderate) may increase the serum concentration of ARIPiprazole.
Citric AcidNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
CodeineCYP2D6 Inhibitors (Moderate) may diminish the therapeutic effect of Codeine. These CYP2D6 inhibitors may prevent the metabolic conversion of codeine to its active metabolite morphine.
ColesevelamMay decrease the absorption of Nonsteroidal Anti-Inflammatory Agents.
DabrafenibMay decrease the serum concentration of CYP2C9 Substrates.
DalteparinNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
DeferasiroxNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
DesmopressinNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Desmopressin.
DicoumarolNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
DigoxinNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Digoxin.
Edetic AcidNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
EliglustatCYP2D6 Inhibitors (Moderate) may increase the serum concentration of Eliglustat.
EnoxaparinNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
EplerenoneNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of Eplerenone. Nonsteroidal Anti-Inflammatory Agents may enhance the hyperkalemic effect of Eplerenone.
Ethyl biscoumacetateNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
FesoterodineCYP2D6 Inhibitors may increase serum concentrations of the active metabolite(s) of Fesoterodine.
FloctafenineMay enhance the adverse/toxic effect of Nonsteroidal Anti-Inflammatory Agents.
Fondaparinux sodiumNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
FramycetinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
GentamicinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
HaloperidolNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Haloperidol. Specifically including drowsiness and confusion.
HeparinNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
HydralazineNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of HydrALAZINE.
KanamycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
LithiumNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Lithium.
MethotrexateNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Methotrexate.
MetoprololCYP2D6 Inhibitors may increase the serum concentration of Metoprolol.
MifepristoneMay increase the serum concentration of CYP2C9 Substrates.
NebivololCYP2D6 Inhibitors (Moderate) may increase the serum concentration of Nebivolol.
NeomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
NetilmicinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
Nitric OxideMay enhance the adverse/toxic effect of Methemoglobinemia Associated Agents. Combinations of these agents may increase the likelihood of significant methemoglobinemia.
PhenindioneNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
PhenprocoumonNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
PorfimerPhotosensitizing Agents may enhance the photosensitizing effect of Porfimer.
PralatrexateNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of PRALAtrexate. More specifically, NSAIDS may decrease the renal excretion of pralatrexate.
PrilocaineMethemoglobinemia Associated Agents may enhance the adverse/toxic effect of Prilocaine. Combinations of these agents may increase the likelihood of significant methemoglobinemia.
ProbenecidMay increase the serum concentration of Nonsteroidal Anti-Inflammatory Agents.
PropafenoneMay increase the serum concentration of CYP2D6 Inhibitors (Moderate).
RibostamycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
SpectinomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
StreptomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
SulodexideNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
TamoxifenCYP2D6 Inhibitors (Moderate) may decrease serum concentrations of the active metabolite(s) of Tamoxifen. Specifically, CYP2D6 inhibitors may decrease the metabolic formation of highly potent active metabolites.
TenofovirNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Tenofovir.
ThioridazineCYP2D6 Inhibitors may increase the serum concentration of Thioridazine.
TobramycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TramadolCYP2D6 Inhibitors (Moderate) may diminish the therapeutic effect of TraMADol. These CYP2D6 inhibitors may prevent the metabolic conversion of tramadol to its active metabolite that accounts for much of its opioid-like effects.
TreprostinilNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
VancomycinNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Vancomycin.
VerteporfinPhotosensitizing Agents may enhance the photosensitizing effect of Verteporfin.
WarfarinNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
Food Interactions
  • Take without regard to meals.
  • Taking this product with a high-fat meal will delay the Cmax, but total absorption will be increased by 10 to 20%.

Targets

1. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. Sigthorsson G, Simpson RJ, Walley M, Anthony A, Foster R, Hotz-Behoftsitz C, Palizban A, Pombo J, Watts J, Morham SG, Bjarnason I: COX-1 and 2, intestinal integrity, and pathogenesis of nonsteroidal anti-inflammatory drug enteropathy in mice. Gastroenterology. 2002 Jun;122(7):1913-23. Pubmed
  2. Scheiman JM: Outcomes studies of the gastrointestinal safety of cyclooxygenase-2 inhibitors. Cleve Clin J Med. 2002;69 Suppl 1:SI40-6. Pubmed
  3. Reddy BS, Rao CV: Novel approaches for colon cancer prevention by cyclooxygenase-2 inhibitors. J Environ Pathol Toxicol Oncol. 2002;21(2):155-64. Pubmed
  4. Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. Pubmed
  5. Lu S, Zhang X, Badawi AF, El-Sohemy A, Archer MC: Cyclooxygenase-2 inhibitor celecoxib inhibits promotion of mammary tumorigenesis in rats fed a high fat diet rich in n-6 polyunsaturated fatty acids. Cancer Lett. 2002 Oct 8;184(1):7-12. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. 3-phosphoinositide-dependent protein kinase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
3-phosphoinositide-dependent protein kinase 1 O15530 Details

References:

  1. Kulp SK, Yang YT, Hung CC, Chen KF, Lai JP, Tseng PH, Fowble JW, Ward PJ, Chen CS: 3-phosphoinositide-dependent protein kinase-1/Akt signaling represents a major cyclooxygenase-2-independent target for celecoxib in prostate cancer cells. Cancer Res. 2004 Feb 15;64(4):1444-51. Pubmed
  2. Zhu J, Huang JW, Tseng PH, Yang YT, Fowble J, Shiau CW, Shaw YJ, Kulp SK, Chen CS: From the cyclooxygenase-2 inhibitor celecoxib to a novel class of 3-phosphoinositide-dependent protein kinase-1 inhibitors. Cancer Res. 2004 Jun 15;64(12):4309-18. Pubmed
  3. Tong Z, Wu X, Ovcharenko D, Zhu J, Chen CS, Kehrer JP: Neutrophil gelatinase-associated lipocalin as a survival factor. Biochem J. 2005 Oct 15;391(Pt 2):441-8. Pubmed
  4. Li J, Zhu J, Melvin WS, Bekaii-Saab TS, Chen CS, Muscarella P: A structurally optimized celecoxib derivative inhibits human pancreatic cancer cell growth. J Gastrointest Surg. 2006 Feb;10(2):207-14. Pubmed
  5. Tseng PH, Wang YC, Weng SC, Weng JR, Chen CS, Brueggemeier RW, Shapiro CL, Chen CY, Dunn SE, Pollak M, Chen CS: Overcoming trastuzumab resistance in HER2-overexpressing breast cancer cells by using a novel celecoxib-derived phosphoinositide-dependent kinase-1 inhibitor. Mol Pharmacol. 2006 Nov;70(5):1534-41. Epub 2006 Aug 3. Pubmed

Enzymes

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Davies NM, McLachlan AJ, Day RO, Williams KM: Clinical pharmacokinetics and pharmacodynamics of celecoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet. 2000 Mar;38(3):225-42. Pubmed
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  3. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. Pubmed
  4. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  6. Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, Shou M: Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):368-74. Pubmed
  7. Rodrigues AD: Impact of CYP2C9 genotype on pharmacokinetics: are all cyclooxygenase inhibitors the same? Drug Metab Dispos. 2005 Nov;33(11):1567-75. Epub 2005 Aug 23. Pubmed

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Werner U, Werner D, Rau T, Fromm MF, Hinz B, Brune K: Celecoxib inhibits metabolism of cytochrome P450 2D6 substrate metoprolol in humans. Clin Pharmacol Ther. 2003 Aug;74(2):130-7. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. FDA label

2. Alpha-1-acid glycoprotein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Alpha-1-acid glycoprotein 1 P02763 Details

References:

  1. FDA label

Transporters

1. Multidrug resistance-associated protein 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance-associated protein 4 O15439 Details

References:

  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:22