Identification

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Name
Celecoxib
Accession Number
DB00482  (APRD00373)
Type
Small Molecule
Groups
Approved, Investigational
Description

Celecoxib, 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.16 It is used to manage symptoms of various types of arthritis pain and in familial adenomatous polyposis (FAP)25 to reduce precancerous polyps in the colon.15 It is marketed by Pfizer under the brand name Celebrex, and was initially granted FDA approval in 1998.27

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.7

Structure
Thumb
Synonyms
  • Celecoxib
  • Célécoxib
  • Celecoxibum
  • p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide
External IDs
SC 58635 / YM 177
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act CelecoxibCapsuleOralActavis Pharma Company2014-11-21Not applicableCanada
Act CelecoxibCapsuleOralActavis Pharma Company2014-11-21Not applicableCanada
CelebrexCapsule400 mg/1OralPhysicians Total Care, Inc.1998-10-022014-06-30Us
CelebrexCapsule200 mgOralPfizer Canada Ulc1999-04-19Not applicableCanada
CelebrexCapsule200 mg/1OralStat Rx USA1998-10-02Not applicableUs
CelebrexCapsule200 mg/1OralBlenheim Pharmacal, Inc.2008-02-012011-11-30Us
CelebrexCapsule200 mg/1OralG.D. Searle LLC Division of Pfizer Inc1998-10-02Not applicableUs0025 152520180812 28838 1s2jgev
CelebrexCapsule100 mg/1OralCardinal Health1998-10-02Not applicableUs55154 362120180913 8702 1e282s0
CelebrexCapsule200 mg/1Oralbryant ranch prepack1998-10-02Not applicableUs
CelebrexCapsule200 mg/1OralKeltman Pharmaceuticals Inc.2006-03-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-celecoxibCapsuleOralAccel Pharma Inc2015-03-262018-04-20Canada
Accel-celecoxibCapsuleOralAccel Pharma Inc2015-03-262018-04-20Canada
Ag-celecoxibCapsuleOralAngita Pharma Inc.2018-06-22Not applicableCanada
Ag-celecoxibCapsuleOralAngita Pharma Inc.2018-06-22Not applicableCanada
Apo-celecoxibCapsuleOralApotex Corporation2014-11-17Not applicableCanada
Apo-celecoxibCapsuleOralApotex Corporation2014-11-17Not applicableCanada
Auro-celecoxibCapsuleOralAuro Pharma Inc2015-12-02Not applicableCanada
Auro-celecoxibCapsuleOralAuro Pharma Inc2015-12-02Not applicableCanada
Bio-celecoxibCapsuleOralBiomed Pharma2014-12-05Not applicableCanada
Bio-celecoxibCapsuleOralBiomed Pharma2014-12-05Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
NuDroxiPAKCelecoxib (200 mg/1) + Capsaicin (0.25 mg/1mL) + Levomenthol (60 mg/1mL) + Methyl salicylate (250 mg/1mL)TopicalNucare Pharmaceuticals,inc.2018-02-08Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CapxibCelecoxib (200 mg/1) + Capsaicin (0.0375 mg/1) + Levomenthol (50 mg/1)KitTopicalMas Management Group2016-04-082018-01-01Us
LidoXibCelecoxib (200 mg/1) + Levomenthol (10 mg/1g) + Lidocaine (40 mg/1g)KitTopicalMas Management Group2015-06-032018-01-01Us
International/Other Brands
Articox (Keyfarm) / Articoxib (Nabiqasim) / Artiflex (Standpharm) / Artilog (Pfizer) / Artix (Pharmalab) / Artrixib (Intipharma) / Blockten (Infarmasa) / Caditar (Farmindustria) / Cefinix (Farmacoop) / Celact (Sun) / Celebra (Pfizer) / Valdyne (Pfizer)
Categories
UNII
JCX84Q7J1L
CAS number
169590-42-5
Weight
Average: 381.372
Monoisotopic: 381.075882012
Chemical Formula
C17H14F3N3O2S
InChI Key
RZEKVGVHFLEQIL-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

Pharmacology

Indication

Celecoxib is indicated for symptomatic treatment of adult osteoarthritis (OA) and adult rheumatoid arthritis (RA).31 Celecoxib is not a substitute for aspirin for cardiovascular event prophylaxis.25,31

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. In addition, celecoxib is used as an adjunct to therapy for patients diagnosed with familial adenomatous polyposis.31

Associated Conditions
Pharmacodynamics

Celecoxib inhibits cyclooxygenase 2 (COX-2) enzyme, reducing pain and inflammation. It is important to note that though the risk of bleeding with celecoxib is lower than with certain other NSAIDS, it exists nonetheless and caution must be observed when it is administered to those with a high risk of gastrointestinal bleeding.28

A note on the risk of cardiovascular events

Significant concerns regarding the safety of COX-2 selective NSAIDs emerged in the early 2000s. Rofecoxib, another member of the COX-2 inhibitor drug class, also known as Vioxx, was withdrawn from the market due to prothrombotic cardiovascular risks.30 Following an FDA Advisory Committee meeting in 2005, in which data from large clinical outcome trials were evaluated, the FDA concluded that the risk for cardiovascular thrombotic events for both COX-2 selective NSAIDs and nonselective NSAIDs was evident.22 It was determined that the benefits of celecoxib treatment, however, outweighed the risks.30 Postmarketing cardiovascular outcomes trial (PRECISION) revealed that the lowest possible dose of celecoxib was similar in cardiovascular safety to moderate strength doses of both naproxen and ibuprofen. Patients who had previous cardiovascular events including acute MI, coronary revascularization, or coronary stent insertion were not evaluated in the trial. It is not advisable to administer NSAIDS to these groups of patients.22

Mechanism of action

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. COX-2 is expressed heavily in inflamed tissues where it is induced by inflammatory mediators.25 The inhibition of this enzyme reduces the synthesis of metabolites that include prostaglandin E2 (PGE2), prostacyclin (PGI2), thromboxane (TXA2), prostaglandin D2 (PGD2), and prostaglandin F2 (PGF2). Resultant inhibition of these mediators leads to the alleviation of pain and inflammation.7,25

By inhibiting prostaglandin synthesis, non-steroidal anti-inflammatory drugs (NSAIDs) cause mucosal damage, ulceration and ulcer complication throughout the gastrointestinal tract.25 Celecoxib poses less of an ulceration risk than other NSAIDS, owing to its decreased effect on gastric mucosal prostaglandin synthesis when compared to placebo.8

Celecoxib exerts anticancer effects by binding to the cadherin-11 (CDH11)protein, which is thought to be involved in the progression of tumors, and inhibiting the 3-phosphoinositide-dependent kinase-1 (PDK-1) signaling mechanism.21,17 In addition, celecoxib has been found to inhibit carbonic anhydrase enzymes 2 and 3, further enhancing its anticancer effects.18,19

As mentioned in the pharmacodynamics section of this drug entry, celecoxib may cause an increased risk of thrombotic events. The risk of thrombosis resulting from COX-2 inhibition is caused by the vasoconstricting actions of thromboxane A2, leading to enhanced platelet aggregation, which is uncontrolled when the actions of prostacyclin, a platelet aggregation inhibitor, are suppressed through the inhibition of COX-2.30

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Humans
U3-phosphoinositide-dependent protein kinase 1
inhibitor
Humans
UCarbonic anhydrase 2
inhibitor
Humans
UCarbonic anhydrase 3
inhibitor
Humans
UCadherin-11
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Celecoxib is absorbed rapidly in the gastrointestinal tract.7 When a single oral dose of 200 mg was given to healthy research subjects, the peak plasma levels of celecoxib occurred within 3 hours.7,25 The Cmax is 705 ng/mL.24 When multiple doses are given, steady-state concentrations are 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%.25 The AUC of celecoxib has been shown to be significantly lower in patients with chronic renal impairment.12,25 A meta-analysis of pharmacokinetic studies has suggested an approximately 40% higher AUC (area under the curve) of celecoxib in black patients compared to Caucasians for unknown reasons.24

Volume of distribution

The apparent volume of distribution of celecoxib at steady state (Vss/F) is about 429 L24, which suggests wide distribution into various tissues. Celecoxib is not preferentially bound to red blood cells.25 Another resource reports a volume of distribution of 455 ± 166L.12

Protein binding

The protein binding of celecoxib is 97%, and it is primarily bound to albumin.12,25

Metabolism

A large part of celecoxib metabolism is mediated by cytochrome P450 2C9 in the liver with some contribution from CYP3A4 and CYP2C8 and possible contributions from CYP2D6.7,20,21 It is metabolized by biotransformation to carboxylic acid and glucuronide metabolites.12 Three metabolites, a primary alcohol, a carboxylic acid, and a glucuronide conjugate, have been found in human plasma after celecoxib administration.7 These are considered inactive metabolites in regards to COX enzyme inhibition. Patients who are known or suspected to have decreased cytochrome P450 2C9 activity or function, based on their previous history, should be administered celecoxib with caution as they may have abnormally high serum concentrations resulting from decreased metabolism celecoxib.25

Route of elimination

Celecoxib is primarily eliminated by hepatic metabolism with small amounts (<3%) of the unchanged drug found in both the urine and feces.12 About 57% of an oral dose of celecoxib is excreted in the feces and 27% is found to be excreted into the urine in the form of metabolites. The main metabolite in urine and feces is identified as the carboxylic acid metabolite (73%). The amount of glucuronide in the urine is reported to be low.25

Half life

The effective half-life of celecoxib is approximately 11 hours when a single 200 mg dose is given to healthy subjects.24,25 The terminal half-life of celecoxib varies because of its low solubility, which prolongs absorption.25

Clearance

Apparent clearance (CL/F), single oral 200 mg dose, healthy subjects = 27.7 L/hr.25 Clearance may be decreased by about 47% in patients with chronic renal insufficiency, according to a pharmacokinetic study. Studies have not been performed in patients with severe renal impairment.25

Toxicity

The oral LD50 of celecoxib in both the rat and dog is >2000 mg/kg.29

It is not advisable to administer celecoxib in patients with renal impairment or advanced hepatic impairment, as this may lead to increased serum concentrations, causing toxicity.25 Symptoms of overdose may include breathing difficulties, coma, drowsiness, gastrointestinal bleeding, high blood pressure, kidney failure, nausea, sluggishness, stomach pain, and vomiting.22 Because serious gastrointestinal tract ulceration and bleeding can occur without preceding symptoms, patients should be monitored for signs/symptoms of gastrointestinal bleeding. Symptomatic and supportive measures should be taken in a celecoxib overdose. The induction of emesis or administration of active charcoal should take place if the patient is seen within 4 hours of celecoxib ingestion. Diuresis, urinary alkalinization, hemodialysis, or hemoperfusion may not be useful in a celecoxib overdose due to its high level of protein binding.25

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Celecoxib Action PathwayDrug action
Celecoxib Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*3(A;C) / (C;C)C AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of celecoxib.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Celecoxib is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Celecoxib is combined with (S)-Warfarin.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Celecoxib can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Celecoxib is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Celecoxib is combined with 1-benzylimidazole.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Celecoxib.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when Celecoxib is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Celecoxib is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Celecoxib.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when Celecoxib is combined with 4-Bromo-2,5-dimethoxyamphetamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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%.

References

Synthesis Reference
US5466823
General References
  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:15208519]
  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:10979111]
  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:15713944]
  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:16777855]
  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:16943400]
  6. 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:12392591]
  7. Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. [PubMed:22336956]
  8. Hawkey CJ: COX-1 and COX-2 inhibitors. Best Pract Res Clin Gastroenterol. 2001 Oct;15(5):801-20. doi: 10.1053/bega.2001.0236. [PubMed:11566042]
  9. Gwee KA, Goh V, Lima G, Setia S: Coprescribing proton-pump inhibitors with nonsteroidal anti-inflammatory drugs: risks versus benefits. J Pain Res. 2018 Feb 14;11:361-374. doi: 10.2147/JPR.S156938. eCollection 2018. [PubMed:29491719]
  10. Chan FKL, Ching JYL, Tse YK, Lam K, Wong GLH, Ng SC, Lee V, Au KWL, Cheong PK, Suen BY, Chan H, Kee KM, Lo A, Wong VWS, Wu JCY, Kyaw MH: Gastrointestinal safety of celecoxib versus naproxen in patients with cardiothrombotic diseases and arthritis after upper gastrointestinal bleeding (CONCERN): an industry-independent, double-blind, double-dummy, randomised trial. Lancet. 2017 Jun 17;389(10087):2375-2382. doi: 10.1016/S0140-6736(17)30981-9. Epub 2017 Apr 11. [PubMed:28410791]
  11. 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. doi: 10.2165/00003088-200038030-00003. [PubMed:10749518]
  12. 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. doi: 10.2165/00002018-200225070-00007. [PubMed:12093311]
  13. Daniels S, Robbins J, West CR, Nemeth MA: Celecoxib in the treatment of primary dysmenorrhea: results from two randomized, double-blind, active- and placebo-controlled, crossover studies. Clin Ther. 2009 Jun;31(6):1192-208. doi: 10.1016/j.clinthera.2009.06.003. [PubMed:19695387]
  14. Frampton JE, Keating GM: Celecoxib: a review of its use in the management of arthritis and acute pain. Drugs. 2007;67(16):2433-72. doi: 10.2165/00003495-200767160-00008. [PubMed:17983259]
  15. Chen QW, Zhang XM, Zhou JN, Zhou X, Ma GJ, Zhu M, Zhang YY, Yu J, Feng JF, Chen SQ: Analysis of Small Fragment Deletions of the APC gene in Chinese Patients with Familial Adenomatous Polyposis, a Precancerous Condition. Asian Pac J Cancer Prev. 2015;16(12):4915-20. doi: 10.7314/apjcp.2015.16.12.4915. [PubMed:26163615]
  16. Shin S: Safety of celecoxib versus traditional nonsteroidal anti-inflammatory drugs in older patients with arthritis. J Pain Res. 2018 Dec 14;11:3211-3219. doi: 10.2147/JPR.S186000. eCollection 2018. [PubMed:30588073]
  17. 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. doi: 10.1158/0008-5472.CAN-03-4063. [PubMed:15205346]
  18. Weber A, Casini A, Heine A, Kuhn D, Supuran CT, Scozzafava A, Klebe G: Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: new pharmacological opportunities due to related binding site recognition. J Med Chem. 2004 Jan 29;47(3):550-7. [PubMed:14736236]
  19. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [PubMed:17826101]
  20. Daily EB, Aquilante CL: Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics. 2009 Sep;10(9):1489-510. doi: 10.2217/pgs.09.82. [PubMed:19761371]
  21. Brandon Cohen; Charles V. Preuss (2019). Celecoxib, NIH StatPearls. StatPearls.
  22. FDA drug safety, June 28 2018 [Link]
  23. Medscape drug reference [Link]
  24. Pfizer Medical Information [Link]
  25. Celecoxib FDA label [Link]
  26. Medicines UK, Celebrex 200mg capsule [Link]
  27. FDA approvals, Celebrex [Link]
  28. Bpac NZ: Celecoxib [Link]
  29. MSDS, Celecoxib [Link]
  30. US Pharmacist: Cardiovascular risk associated with NSAIDS and COX2 inhibitors [Link]
  31. FDA label, updated [Link]
External Links
Human Metabolome Database
HMDB0005014
KEGG Drug
D00567
KEGG Compound
C07589
PubChem Compound
2662
PubChem Substance
46505596
ChemSpider
2562
BindingDB
11639
ChEBI
41423
ChEMBL
CHEMBL118
Therapeutic Targets Database
DAP000737
PharmGKB
PA448871
HET
CEL
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Celecoxib
ATC Codes
M01AH01 — CelecoxibL01XX33 — CelecoxibG01AE10 — Combinations of sulfonamides
AHFS Codes
  • 28:08.04.08 — Cyclooxygenase-2 (COX-2) Inhibitors
PDB Entries
1oq5 / 3kk6 / 3ln1 / 4fim / 5jw1

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentStage IA Breast Cancer / Stage IB Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
0CompletedBasic ScienceBMI >30 kg/m21
0CompletedBasic ScienceMajor Depressive Disorder (MDD)1
0Not Yet RecruitingPreventionHealthy Volunteers1
0RecruitingTreatmentAnatomic Stage IV Breast Cancer AJCC / Estrogen Receptor Negative / HER2/Neu Negative / Progesterone Receptor Negative / Triple -Negative Breast Cancer1
0RecruitingTreatmentMeniscus Disorder / Narcotic Use1
0TerminatedBasic ScienceBone Ingrowth / Pain NOS1
0Unknown StatusPreventionSmoking / Tobacco Use Disorders1
1Active Not RecruitingTreatmentGlioblastomas1
1Active Not RecruitingTreatmentNeuroblastomas1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedNot AvailableCancer, Breast1
1CompletedNot AvailableHealthy Volunteers2
1CompletedBasic ScienceHealthy Volunteers7
1CompletedOtherHealthy Male Volunteers1
1CompletedOtherHealthy Volunteers1
1CompletedOtherMigraine1
1CompletedOtherQt Interval, Variation in1
1CompletedPreventionCancer, Breast1
1CompletedPreventionColorectal Cancers / Precancerous Conditions1
1CompletedPreventionHead and Neck Carcinoma1
1CompletedTreatmentAdvanced Esophageal Cancers / Cancers of Non-thoracic Origin With Metastases to the Lungs or Pleura / Lung Cancer Non-Small Cell Cancer (NSCLC) / Pleural Mesotheliomas / Primary Small Cell Lung Cancers1
1CompletedTreatmentChildhood Malignant Fibrous Histiocytoma of Bone / Sarcomas1
1CompletedTreatmentColorectal Cancers / Severe or persistent diarrhea1
1CompletedTreatmentEpithelial Malignancies / Melanoma / Pleural Malignancy / Sarcomas1
1CompletedTreatmentEsophageal Cancers / Lung Cancers / Malignant Pleural Mesothelioma (MPM) / Sarcomas / Thymic Carcinoma1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHereditary Nonpolyposis / Neoplasms, Colorectal1
1CompletedTreatmentLung Cancers3
1CompletedTreatmentNeoplasms, Hepatic1
1CompletedTreatmentNon-Small Cell Lung Cancer Recurrent / Stage IIIb Non-small Cell Lung Cancer / Stage IV Non-Small Cell Lung Cancer1
1CompletedTreatmentOrthopaedic Related Pain (Musculoskeletal Pain)1
1CompletedTreatmentPain NOS1
1CompletedTreatmentPostoperative pain1
1CompletedTreatmentRelapsed Multiple Myeloma1
1CompletedTreatmentStage I Breast Carcinoma / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer1
1CompletedTreatmentTuberculosis Infection1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific3
1Not Yet RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1RecruitingBasic ScienceElectrophysiologic Property of Brain1
1RecruitingDiagnosticMuscle Inflammation1
1RecruitingOtherHealthy Volunteers1
1RecruitingPreventionActinic Keratosis (AK) / Therapy, Photodynamic1
1RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Cancer, Breast / Malignant Neoplasm of Pancreas / Prostate Cancer1
1RecruitingTreatmentBladder Cancers1
1RecruitingTreatmentGliomas1
1RecruitingTreatmentMalignant Neoplasm of Colon / MSI-H1
1TerminatedBasic ScienceHealthy Volunteers1
1TerminatedTreatmentCancer, Breast1
1TerminatedTreatmentEpithelial Malignancies / Melanoma / Pleural Malignancy / Sarcomas1
1TerminatedTreatmentAdvanced thymic carcinoma / Esophageal Cancers / Lung Cancers / Mesolthelioma / Thoracic Sarcomas1
1TerminatedTreatmentHealthy Volunteers1
1TerminatedTreatmentInflammatory Reaction1
1TerminatedTreatmentMalignant Neoplasm of Pancreas1
1WithdrawnBasic ScienceLung Cancer Non-Small Cell Cancer (NSCLC)1
1WithdrawnTreatmentMelanoma / Neoplasms Metastasis / Neoplasms, Germ Cell and Embryonal / Sarcomas1
1, 2Active Not RecruitingTreatmentColorectal Cancers / Malignant Neoplasm of Colon1
1, 2CompletedBasic ScienceCardiovascular Disease (CVD) / High Blood Pressure (Hypertension) / Obstructive Sleep Apnea (OSA) / Strokes1
1, 2CompletedBasic ScienceMouth Neoplasms1
1, 2CompletedDiagnosticPrecancerous Conditions1
1, 2CompletedPreventionBiomarker Change Linked to Breast Cancer1
1, 2CompletedPreventionCancer, Breast1
1, 2CompletedPreventionTobacco Use Disorders1
1, 2CompletedTreatmentAdvanced Melanoma1
1, 2CompletedTreatmentCervical Cancers1
1, 2CompletedTreatmentCervix Neoplasms1
1, 2CompletedTreatmentLiver Cancer1
1, 2CompletedTreatmentLung Cancers2
1, 2CompletedTreatmentMalignancies1
1, 2CompletedTreatmentMalignant Neoplasm of Pancreas Metastatic to Peritoneal Surface / Malignant Peritoneal Mesothelioma / Peritoneal Carcinomatosis1
1, 2CompletedTreatmentNasopharyngeal Carcinoma1
1, 2CompletedTreatmentNeoplasms, Colorectal1
1, 2Not Yet RecruitingTreatmentAnatomic Stage 0 Breast Cancer AJCC v8 / Anatomic Stage I Breast Cancer AJCC v8 / Anatomic Stage IA Breast Cancer AJCC v8 / Anatomic Stage IB Breast Cancer AJCC v8 / Anatomic Stage II Breast Cancer AJCC v8 / Anatomic Stage IIA Breast Cancer AJCC v8 / Anatomic Stage IIB Breast Cancer AJCC v8 / Early-Stage Breast Carcinoma / Estrogen Receptor Negative / HER2/Neu Negative / Progesterone Receptor Negative / Prognostic Stage 0 Breast Cancer AJCC v8 / Prognostic Stage I Breast Cancer AJCC v8 / Prognostic Stage IA Breast Cancer AJCC v8 / Prognostic Stage IB Breast Cancer AJCC v8 / Prognostic Stage II Breast Cancer AJCC v8 / Prognostic Stage IIA Breast Cancer AJCC v8 / Prognostic Stage IIB Breast Cancer AJCC v8 / Triple-Negative Breast Carcinoma1
1, 2Not Yet RecruitingTreatmentArthritis / BMI >30 kg/m2 / High Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
1, 2RecruitingTreatmentCancer of the Ovary / Neoplasms, Ovarian / Ovary Neoplasms1
1, 2SuspendedTreatmentCancers of Non-thoracic Origin With Metastases to the Lungs or Pleura / Esophageal Cancers / Lung Cancers / Malignant Pleural Mesothelioma (MPM) / Melanoma / Sarcomas / Thoracic Sarcomas / Thorasic Cancers / Thymic Carcinoma1
1, 2TerminatedTreatmentCarcinoma, Colorectal / Colorectal Cancers / Colorectal Tumors / Neoplasms, Colorectal1
1, 2Unknown StatusTreatmentCancer of the Head / Cancer of the Larynx / Cancer of the Neck / Cancer of the Pharynx / Paranasal Sinus Neoplasms1
1, 2Unknown StatusTreatmentHead and Neck Carcinoma1
1, 2WithdrawnTreatmentLiver Cancer1
2Active Not RecruitingTreatmentCarcinoma of Buccal Mucosa / Head and Neck Carcinoma / Oral Squamous Cell Carcinoma / Tongue Cancers1
2Active Not RecruitingTreatmentColorectal Cancers1
2Active Not RecruitingTreatmentEsophageal Cancers1
2Active Not RecruitingTreatmentFallopian Tube Cancer / Peritoneal Cavity Cancer / Recurrent Ovarian Epithelial Cancer1
2Active Not RecruitingTreatmentFamilial Adenomatous Polyposis (FAP)1
2Active Not RecruitingTreatmentKnee Replacement Surgery / Postoperative pain1
2Active Not RecruitingTreatmentLymphangioleiomyomatosis (LAM)1
2Active Not RecruitingTreatmentNeurofibromatosis 11
2CompletedNot AvailableMetastatic Hormone Refractory Prostate Cancer1
2CompletedDiagnosticNeoplasms1
2CompletedPreventionCancer, Breast2
2CompletedPreventionCervical Cancers / Cervical Carcinoma / Cervical Intraepithelial Neoplasia Grade 2 / Cervical Intraepithelial Neoplasia Grade 2/3 / Cervical Intraepithelial Neoplasia Grade 3 / Stage 0 Cervical Cancer1
2CompletedPreventionColorectal Cancers1
2CompletedPreventionEsophageal Cancers1
2CompletedPreventionHead and Neck Carcinoma1
2CompletedPreventionHead and Neck Carcinoma / Precancerous Conditions1
2CompletedPreventionLung Cancers2
2CompletedPreventionMonoclonal Gammopathy of Undetermined Significance (MGUS) / Multiple Myeloma (MM) / Smoldering Multiple Myeloma (SMM)1
2CompletedPreventionNo Evidence of Disease2
2CompletedPreventionNon-Melanomatous Skin Cancer1
2CompletedPreventionOral Mucositis1
2CompletedPreventionPrecancerous Conditions1
2CompletedPreventionProstate Cancer1
2CompletedSupportive CarePain NOS1
2CompletedSupportive CareTonsillitis1
2CompletedTreatmentAdenotonsillectomy / Postoperative pain / Tonsillectomy1
2CompletedTreatmentAllodynia / Migraine With Aura / Migraine Without Aura1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2CompletedTreatmentAnaplastic Glioma of Brain / Brain Cancer / Glioblastoma Multiforme (GBM)1
2CompletedTreatmentBack Pain Lower Back Chronic / Subacute Low Back Pain1
2CompletedTreatmentBenign Prostatic Hyperplasia (BPH)1
2CompletedTreatmentBrain Stem Gliomas1
2CompletedTreatmentBrain and Central Nervous System Tumors1
2CompletedTreatmentCancer, Breast4
2CompletedTreatmentCancer, Breast / Neoplasms, Breast1
2CompletedTreatmentCarcinoma, Colorectal / Colorectal Adenomas1
2CompletedTreatmentCentral Nervous System Tumor, Pediatric / Leukemias / Malignant Lymphomas / Neuroblastomas / Sarcomas / Unspecified Childhood Solid Tumor, Protocol Specific1
2CompletedTreatmentColorectal Cancers4
2CompletedTreatmentDental Pain3
2CompletedTreatmentEsophageal Cancers2
2CompletedTreatmentFacial Pain1
2CompletedTreatmentHead and Neck Carcinoma1
2CompletedTreatmentHead and Neck Carcinoma / Lung Cancers1
2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentLocally Advanced Rectal Cancer1
2CompletedTreatmentLung Cancers5
2CompletedTreatmentMacular Degeneration1
2CompletedTreatmentMalignant Neoplasm of Pancreas2
2CompletedTreatmentNeoplasms, Breast1
2CompletedTreatmentNeoplasms, Ovarian1
2CompletedTreatmentNon Muscle Invasive Bladder Cancer1
2CompletedTreatmentNon Small Cell Lung Carcinoma (NSCLC)1
2CompletedTreatmentNon-Small Cell Lung Cancer Recurrent / Stage IIIb Non-small Cell Lung Cancer / Stage IV Non-Small Cell Lung Cancer2
2CompletedTreatmentOsteoarthritis (OA)1
2CompletedTreatmentPain NOS1
2CompletedTreatmentPain, Acute2
2CompletedTreatmentPostoperative pain1
2CompletedTreatmentProstate Cancer1
2CompletedTreatmentRecurrent Respiratory Papillomatosis1
2CompletedTreatmentRenal Cell Adenocarcinoma / Stage IV Renal Cell Cancer1
2CompletedTreatmentSarcomas1
2CompletedTreatmentSchizophrenic Disorders1
2CompletedTreatmentTemporomandibular Joint Disorders1
2CompletedTreatmentTonsillectomy1
2Enrolling by InvitationDiagnosticKnee Osteoarthritis (Knee OA) / Osteoarthritis, Hip1
2Enrolling by InvitationTreatmentChronic Back Pain1
2Not Yet RecruitingTreatmentEndometrium Cancer1
2Not Yet RecruitingTreatmentHLA-A2 Positive Cells Present / Refractory Melanoma1
2Not Yet RecruitingTreatmentKnee Osteoarthritis (Knee OA)1
2Not Yet RecruitingTreatmentMetastatic Cancers1
2RecruitingPreventionOral Squamous Cell Carcinoma1
2RecruitingPreventionPain, Neuropathic1
2RecruitingSupportive CareCancer of the Breast / Cancer, Breast / Malignant Neoplasm of Female Breast1
2RecruitingTreatmentAnkylosing Spondylitis (AS)1
2RecruitingTreatmentChemotherapy Effect / Malignant Neoplasm of Pancreas1
2RecruitingTreatmentColon Carcinoma1
2RecruitingTreatmentKnee Replacement Surgery / Manipulation1
2RecruitingTreatmentMalignancies1
2RecruitingTreatmentMedulloblastomas1
2RecruitingTreatmentMetastatic Carcinoma in the Liver / Recurrent Colorectal Carcinoma / Stage IV Colorectal Cancer AJCC v7 / Stage IVA Colorectal Cancer AJCC v7 / Stage IVB Colorectal Cancer AJCC v71
2RecruitingTreatmentRecurrent Neuroblastoma1
2RecruitingTreatmentRotator Cuff Syndrome1
2RecruitingTreatmentSpinal Muscular Atrophy (SMA)1
2RecruitingTreatmentThyroid Eye Disease1
2RecruitingTreatmentTumors, Solid1
2TerminatedNot AvailableUterine Malignancies1
2TerminatedPreventionCancer, Breast1
2TerminatedPreventionPancreas Neoplasms1
2TerminatedTreatmentAdenocarcinoma of the Prostate / Prostate Cancer1
2TerminatedTreatmentBrain and Central Nervous System Tumors1
2TerminatedTreatmentBreast Cancer, Metastatic / Cancer treatment1
2TerminatedTreatmentCancer of the Ovary / Primary Peritoneal Cavity Cancer1
2TerminatedTreatmentCancer, Breast2
2TerminatedTreatmentColorectal Cancers1
2TerminatedTreatmentColorectal Cancers / Familial Adenomatous Polyposis (FAP)1
2TerminatedTreatmentEsophageal Cancers1
2TerminatedTreatmentGastric Carcinoma / Gastroesophageal Junction Carcinoma1
2TerminatedTreatmentHead and Neck Carcinoma / Lung Cancers1
2TerminatedTreatmentKnee Osteoarthritis (Knee OA)1
2TerminatedTreatmentLaryngeal Papilloma1
2TerminatedTreatmentLung Cancers1
2TerminatedTreatmentMetastatic Cancers / Prostate Cancer1
2TerminatedTreatmentMetastatic Colorectal Cancers1
2TerminatedTreatmentNeoplasms Metastasis / Neoplasms, Colorectal1
2TerminatedTreatmentOvarian Carcinoma1
2TerminatedTreatmentProstate Cancer1
2TerminatedTreatmentRecurrent Colon Carcinoma / Recurrent Rectal Carcinoma / Stage IVA Colon Cancer / Stage IVA Rectal Cancer / Stage IVB Colon Cancer / Stage IVB Rectal Cancer1
2TerminatedTreatmentRheumatoid Arthritis1
2Unknown StatusPreventionHead and Neck Carcinoma1
2Unknown StatusSupportive CareKnee Osteoarthritis (Knee OA)1
2Unknown StatusTreatmentBrain and Central Nervous System Tumors2
2Unknown StatusTreatmentColorectal Cancers1
2Unknown StatusTreatmentHead and Neck Carcinoma1
2Unknown StatusTreatmentLung Cancers2
2Unknown StatusTreatmentProstate Cancer2
2WithdrawnBasic ScienceCarcinoma, Breast1
2WithdrawnPreventionNon-Melanomatous Skin Cancer1
2WithdrawnTreatmentHigh-Grade Squamous Intraepithelial Lesions / Stage 0 Cervical Cancer1
2WithdrawnTreatmentMetastatic Colorectal Cancers1
2WithdrawnTreatmentPreeclampsia1
2, 3CompletedPreventionDuodenal Neoplasms / Duodenal Polyps / Familial Adenomatous Polyposis (FAP)1
2, 3CompletedPreventionRecurrent Bladder Cancer1
2, 3CompletedTreatmentProstate Cancer1
2, 3RecruitingTreatmentAnterior Cruciate Ligament Injury1
2, 3RecruitingTreatmentNarcotic Use1
2, 3RecruitingTreatmentProstate Cancer1
2, 3TerminatedTreatmentOral Cavity Cancer1
2, 3WithdrawnPreventionPrecancerous Conditions1
3Active Not RecruitingTreatmentColorectal Cancers1
3Active Not RecruitingTreatmentKnee Osteoarthritis (Knee OA) / Osteoarthritis (OA)1
3CompletedPreventionAlzheimer's Disease (AD)1
3CompletedPreventionMalignant Neoplasm of Colon / Rectal Carcinoma1
3CompletedPreventionPrevention / Smoking1
3CompletedSupportive CareCelebrex / Pelubiprofen / Rheumatoid Arthritis1
3CompletedTreatmentAcute Gouty Arthritis1
3CompletedTreatmentAcute Post-surgical Pain1
3CompletedTreatmentAnkylosing Spondylitis (AS)2
3CompletedTreatmentAnterior Cruciate Ligament Injury1
3CompletedTreatmentArthritis / Bleeding Ulcers1
3CompletedTreatmentArthritis / Cardiovascular Disease (CVD) / Cerebrovascular Diseases1
3CompletedTreatmentArthritis / Gastric Ulcer (GU)1
3CompletedTreatmentBack Pain Lower Back3
3CompletedTreatmentBipolar Disorder (BD) / Depression / Depression, Bipolar / Moods Disorders1
3CompletedTreatmentCancer, Breast1
3CompletedTreatmentColorectal Adenomas1
3CompletedTreatmentColorectal Cancers2
3CompletedTreatmentHigh Blood Pressure (Hypertension)2
3CompletedTreatmentKnee Osteoarthritis (Knee OA)7
3CompletedTreatmentLiver Cancer / Postoperative pain1
3CompletedTreatmentMacular Degeneration1
3CompletedTreatmentMalignant Childhood Neoplasm1
3CompletedTreatmentMemory Disorders1
3CompletedTreatmentMetastatic Breast Cancer (MBC)1
3CompletedTreatmentMigraine2
3CompletedTreatmentOsteoarthritis (OA)9
3CompletedTreatmentOsteoarthritis (OA) / Pain NOS1
3CompletedTreatmentOsteoarthritis (OA) / Peptic Ulcers1
3CompletedTreatmentOther Acute Postoperative Pain2
3CompletedTreatmentPain NOS1
3CompletedTreatmentPain, Acute2
3CompletedTreatmentPain, Chronic1
3CompletedTreatmentPharyngitis1
3CompletedTreatmentPost Operative Pain1
3CompletedTreatmentPostoperative pain1
3CompletedTreatmentRheumatoid Arthritis, Juvenile1
3Not Yet RecruitingTreatmentBipolar Disorder (BD) / Postpartum Depression1
3RecruitingPreventionHysteroscopy2
3RecruitingTreatmentAnalgesia1
3RecruitingTreatmentInfluenza, Human1
3RecruitingTreatmentLiver Cancer1
3RecruitingTreatmentMalignant Pleural Mesothelioma (MPM)1
3RecruitingTreatmentNasopharyngeal Carcinoma1
3RecruitingTreatmentOpioids Use / Shoulder Pain1
3SuspendedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
3TerminatedPreventionAdenomatous Polyposis Coli1
3TerminatedPreventionColorectal Cancers1
3TerminatedPreventionOsteoarthritis (OA)1
3TerminatedSupportive CareCancer, Breast / Colorectal Cancers / Pain NOS1
3TerminatedTreatmentLung Cancers1
3Unknown StatusNot AvailableMalignant Neoplasm of Pancreas1
3Unknown StatusTreatmentColon Neoplasms1
3Unknown StatusTreatmentHead and Neck Carcinoma1
3Unknown StatusTreatmentLocalized Primary Osteoarthritis of Hip / Localized Primary Osteoarthritis of Knee1
3Unknown StatusTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
4Active Not RecruitingSupportive CareReverse or Primary Total Shoulder / Rotator Cuff- Full Thickness- Repair1
4Active Not RecruitingTreatmentAnkylosing Spondylitis (AS)1
4CompletedNot AvailableCelecoxib / Function / Minimally Invasive Total Knee Arthroplasty / Pain Management1
4CompletedNot AvailableGastroduodenal Ulcers1
4CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
4CompletedBasic ScienceIschaemic Heart Diseases / Osteoarthritis (OA)1
4CompletedPreventionArthroscopy2
4CompletedPreventionHealthy Volunteers1
4CompletedPreventionPeptic Ulcers1
4CompletedPreventionPostoperative pain1
4CompletedTreatmentAnalgesics1
4CompletedTreatmentAnkle Sprains1
4CompletedTreatmentAnkylosing Spondylitis (AS)1
4CompletedTreatmentAnkylosing Spondylitis (AS) / Inflammatory Reaction1
4CompletedTreatmentBack Pain1
4CompletedTreatmentBack Pain Lower Back2
4CompletedTreatmentBowel Diseases, Inflammatory1
4CompletedTreatmentColorectal Cancers1
4CompletedTreatmentColorectal Disorders1
4CompletedTreatmentCoronary Arteriosclerosis1
4CompletedTreatmentCyclooxygenase 2 Inhibitors / Postoperative pain / Thyroidectomy1
4CompletedTreatmentHealthy Volunteers2
4CompletedTreatmentHepatocellular,Carcinoma1
4CompletedTreatmentHypertension and Coronary Artery Disease1
4CompletedTreatmentInflammatory Reaction / Pain NOS1
4CompletedTreatmentKnee Osteoarthritis (Knee OA)7
4CompletedTreatmentKnee Osteoarthritis (Knee OA) / Osteoarthritis, Hip1
4CompletedTreatmentMagnetic Resonance Imaging (MRI) / Spondylarthropathy1
4CompletedTreatmentNarcotic Use / Nausea / Occasional Constipation / Pain NOS1
4CompletedTreatmentOsteoarthritis (OA)2
4CompletedTreatmentOsteoarthritis (OA) / Rheumatoid Arthritis2
4CompletedTreatmentOsteoarthritis, Hip1
4CompletedTreatmentPostoperative Pain Management / Total Knee Arthroplasty (TKA)1
4CompletedTreatmentPostoperative pain1
4CompletedTreatmentRheumatoid Arthritis1
4CompletedTreatmentRheumatoid Arthritis, Juvenile1
4CompletedTreatmentRotator Cuff Syndrome1
4Enrolling by InvitationTreatmentBile Duct Carcinoma / Malignant Neoplasm of Pancreas1
4Enrolling by InvitationTreatmentNonspecific Pain Post Traumatic Injury1
4Not Yet RecruitingTreatmentAnkylosing Spondylitis (AS)1
4Not Yet RecruitingTreatmentOpioids Use1
4Not Yet RecruitingTreatmentPerineal Pain1
4Not Yet RecruitingTreatmentPharmacokinetics of Celecoxib in Children1
4RecruitingBasic ScienceCardiovascular Disease (CVD) / Rheumatoid Arthritis1
4RecruitingPreventionColposcopy1
4RecruitingPreventionPain NOS1
4RecruitingTreatmentAnkylosing Spondylitis (AS) / Spondyloarthritis, Axial1
4RecruitingTreatmentColon Cancer Stage1
4RecruitingTreatmentDepression / Inflammatory Reaction1
4RecruitingTreatmentKnee Osteoarthritis (Knee OA)1
4RecruitingTreatmentLigament Injury1
4RecruitingTreatmentOsteoarthritis (OA)1
4RecruitingTreatmentOsteoarthritis of the Hands1
4RecruitingTreatmentPain Management1
4RecruitingTreatmentPostoperative pain / Urethral Strictures1
4RecruitingTreatmentRheumatoid Arthritis1
4RecruitingTreatmentSchizophrenic Disorders1
4TerminatedNot AvailableFamilial Adenomatous Polyposis (FAP)1
4TerminatedTreatmentBack Pain Lower Back Chronic1
4TerminatedTreatmentChronic Low Back Pain With a Neuropathic Component1
4TerminatedTreatmentCrohn's Disease (CD)1
4TerminatedTreatmentKnee Osteoarthritis (Knee OA)1
4TerminatedTreatmentOsteoarthritis (OA) / Pain NOS1
4TerminatedTreatmentPain NOS1
4TerminatedTreatmentPostoperative pain1
4TerminatedTreatmentUterine Artery Embolization / Uterine Leiomyomas1
4Unknown StatusTreatmentAngioplasty, Transluminal, Percutaneous Coronary / Coronary Artery Restenosis1
4Unknown StatusTreatmentKnee Osteoarthritis (Knee OA)1
4Unknown StatusTreatmentPain NOS1
4WithdrawnTreatmentBenign Prostatic Hyperplasia (BPH)1
4WithdrawnTreatmentPost Operative Pain Control1
4WithdrawnTreatmentPostoperative pain / Renal Stones1
4WithdrawnTreatmentUreteral Calculus1
Not AvailableCompletedNot AvailableAnkylosing Spondylitis (AS)1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableOsteoarthritis (OA)1
Not AvailableCompletedNot AvailablePatients With Traumatic Pain, Post-surgical Pain and Tooth Extract Pain1
Not AvailableCompletedDiagnosticGonadotropin and Ovarian Hormone Levels (FSH, LH, E2, P) / Menstrual Cycles (Total Length, Bleeding Days) / Ovulation (Follicular Rupture Yes/no)1
Not AvailableCompletedDiagnosticLuteal Development / Ovulation1
Not AvailableCompletedPreventionAlzheimer's Disease (AD) / Dementias1
Not AvailableCompletedPreventionIUD Insertion Pain1
Not AvailableCompletedScreeningHealthy Volunteers1
Not AvailableCompletedTreatmentAntiphospholipid Antibody Syndrome1
Not AvailableCompletedTreatmentHip Labral Tears1
Not AvailableCompletedTreatmentIntracerebral Hemorrhage1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)1
Not AvailableCompletedTreatmentLung Cancers1
Not AvailableCompletedTreatmentPain NOS1
Not AvailableCompletedTreatmentSchizophrenic Disorders1
Not AvailableCompletedTreatmentSpinal Stenosis of Lumbar Region1
Not AvailableCompletedTreatmentSquamous Cell Carcinoma (SCC)1
Not AvailableCompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
Not AvailableCompletedTreatmentUrinary Tract Infections (UTIs)1
Not AvailableEnrolling by InvitationTreatmentRheumatic Pain1
Not AvailableNot Yet RecruitingPreventionPrevention of Post Operative Ileus1
Not AvailableNot Yet RecruitingTreatmentOsteoarthritis (OA)1
Not AvailableNot Yet RecruitingTreatmentPulpitis dental1
Not AvailableRecruitingNot AvailableAcute Non-specific Low Back Pain1
Not AvailableRecruitingPreventionOssification, Heterotopic1
Not AvailableRecruitingTreatmentBack Pain Lower Back1
Not AvailableRecruitingTreatmentFemale Genital Disease1
Not AvailableRecruitingTreatmentHip Pain Chronic1
Not AvailableRecruitingTreatmentKnee Osteoarthritis (Knee OA)1
Not AvailableRecruitingTreatmentStiffness Following Total Knee Arthroplasty1
Not AvailableRecruitingTreatmentTreatment Outcomes1
Not AvailableTerminatedNot AvailableKnee Osteoarthritis (Knee OA)1
Not AvailableTerminatedNot AvailableOsteoarthritis (OA)1
Not AvailableTerminatedNot AvailableRheumatoid Arthritis, Juvenile1
Not AvailableTerminatedTreatmentColorectal Cancers1
Not AvailableTerminatedTreatmentColorectal Cancers / Malignant Neoplasm of Colon1
Not AvailableTerminatedTreatmentDiabetic Nephropathies1
Not AvailableTerminatedTreatmentPain NOS1
Not AvailableUnknown StatusNot AvailableHip Fractures1
Not AvailableUnknown StatusTreatmentAcute Respiratory Distress Syndrome (ARDS) / Blunt Chest Trauma1
Not AvailableUnknown StatusTreatmentHealthy Volunteers1
Not AvailableUnknown StatusTreatmentPostoperative pain2
Not AvailableWithdrawnPreventionBrca1 Mutation Carrier / Brca2 Mutation Carrier / Cancer of the Ovary1
Not AvailableWithdrawnSupportive CareCachexia / Cancer of the Ovary / Malignant Lymphomas / Melanoma (Skin) / Pain NOS / Sarcomas / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableWithdrawnTreatmentBladder Cancers1

Pharmacoeconomics

Manufacturers
  • Gd searle llc
Packagers
  • 4uOrtho LLC
  • Apotheca Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • Cardinal Health
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • GD Searle LLC
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
CapsuleOral100 mg
CapsuleOral100 mg/1
CapsuleOral200 mg/1
CapsuleOral400 mg/1
CapsuleOral50 mg/1
Kit100 mg/1
KitTopical
CapsuleOral200 mg
CapsuleOral400 mg
CapsuleOral
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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5972986No1999-10-262018-04-14Us
CA2267186No2002-05-142017-10-14Canada
CA2177576No1999-10-262014-11-14Canada
US9662315No2017-05-302030-02-28Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)157-159https://www.trc-canada.com/product-detail/?C251000
boiling point (°C)529.0±60.0http://www.chemspider.com/Chemical-Structure.2562.html
water solubilityPoorly solublehttps://www.lclabs.com/products/c-1502-celecoxib
logP3.53https://s3-us-west-2.amazonaws.com/drugbank/msds/DB00482.pdf?1530223672
Caco2 permeability13https://www.tandfonline.com/doi/full/10.3109/10717544.2014.916767
pKa11.1https://www.pfizermedicalinformation.com/en-us/celebrex/description
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorInhibitor0.6172
CYP450 2D6 inhibitorNon-inhibitor0.8594
CYP450 2C19 inhibitorInhibitor0.7169
CYP450 3A4 inhibitorInhibitor0.7959
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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0029000000-1a5ed66ff895eeb127ce
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0129000000-a967b7f9e88a461e3db4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01q9-2598000000-f71f4f9eb7c83ddf79f4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0029000000-13ff69b3abd31dde6bae

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Pyrazoles
Direct Parent
Phenylpyrazoles
Alternative Parents
Benzenesulfonamides / Benzenesulfonyl compounds / Toluenes / Organosulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides
show 3 more
Substituents
Phenylpyrazole / Benzenesulfonamide / Benzenesulfonyl group / Toluene / Monocyclic benzene moiety / Organosulfonic acid amide / Benzenoid / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, pyrazoles, sulfonamide (CHEBI:41423)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
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:12055598]
  2. Scheiman JM: Outcomes studies of the gastrointestinal safety of cyclooxygenase-2 inhibitors. Cleve Clin J Med. 2002;69 Suppl 1:SI40-6. [PubMed:12086292]
  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:12086402]
  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. doi: 10.2165/00002018-200225070-00007. [PubMed:12093311]
  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:12104042]
  6. Celecoxib FDA label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/threonine kinase which acts as a master kinase, phosphorylating and activating a subgroup of the AGC family of protein kinases. Its targets include: protein kinase B (PKB/AKT1, PKB/AKT2, PKB...
Gene Name
PDPK1
Uniprot ID
O15530
Uniprot Name
3-phosphoinositide-dependent protein kinase 1
Molecular Weight
63151.305 Da
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:14973075]
  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. doi: 10.1158/0008-5472.CAN-03-4063. [PubMed:15205346]
  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:16060857]
  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:16455452]
  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:16887935]
Details
3. Carbonic anhydrase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [PubMed:17826101]
  2. Weber A, Casini A, Heine A, Kuhn D, Supuran CT, Scozzafava A, Klebe G: Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: new pharmacological opportunities due to related binding site recognition. J Med Chem. 2004 Jan 29;47(3):550-7. [PubMed:14736236]
Details
4. Carbonic anhydrase 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
Gene Name
CA3
Uniprot ID
P07451
Uniprot Name
Carbonic anhydrase 3
Molecular Weight
29557.215 Da
References
  1. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [PubMed:17826101]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Cadherins are calcium-dependent cell adhesion proteins.
Specific Function
Calcium ion binding
Gene Name
CDH11
Uniprot ID
H3BUU9
Uniprot Name
Cadherin-11
Molecular Weight
73792.615 Da
References
  1. Assefnia S, Dakshanamurthy S, Guidry Auvil JM, Hampel C, Anastasiadis PZ, Kallakury B, Uren A, Foley DW, Brown ML, Shapiro L, Brenner M, Haigh D, Byers SW: Cadherin-11 in poor prognosis malignancies and rheumatoid arthritis: common target, common therapies. Oncotarget. 2014 Mar 30;5(6):1458-74. doi: 10.18632/oncotarget.1538. [PubMed:24681547]
  2. Brandon Cohen; Charles V. Preuss (2019). Celecoxib, NIH StatPearls. StatPearls.

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. [PubMed:22336956]
Details
2. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
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. doi: 10.2165/00003088-200038030-00003. [PubMed:10749518]
  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:19515014]
  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:20167001]
  4. 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:11259318]
  5. 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:16118328]
  6. Brandon Cohen; Charles V. Preuss (2019). Celecoxib, NIH StatPearls. StatPearls.
  7. Flockhart Table of Drug Interactions [Link]
  8. Celecoxib FDA label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
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:12891223]
  2. Siu YA, Hao MH, Dixit V, Lai WG: Celecoxib is a substrate of CYP2D6: Impact on celecoxib metabolism in individuals with CYP2C9*3 variants. Drug Metab Pharmacokinet. 2018 Oct;33(5):219-227. doi: 10.1016/j.dmpk.2018.06.001. Epub 2018 Jun 19. [PubMed:30219715]
  3. Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. [PubMed:22336956]
  4. Molden E, Braathen P: Celecoxib is often combined with cytochrome P450 2D6 substrates in general clinical practice. Clin Pharmacol Ther. 2005 Jul;78(1):93. doi: 10.1016/j.clpt.2005.04.009. [PubMed:16003301]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Daily EB, Aquilante CL: Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics. 2009 Sep;10(9):1489-510. doi: 10.2217/pgs.09.82. [PubMed:19761371]
  2. Brandon Cohen; Charles V. Preuss (2019). Celecoxib, NIH StatPearls. StatPearls.

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
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:12835412]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Pagliarulo V, Ancona P, Niso M, Colabufo NA, Contino M, Cormio L, Azzariti A, Pagliarulo A: The interaction of celecoxib with MDR transporters enhances the activity of mitomycin C in a bladder cancer cell line. Mol Cancer. 2013 May 24;12:47. doi: 10.1186/1476-4598-12-47. [PubMed:23705854]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Pagliarulo V, Ancona P, Niso M, Colabufo NA, Contino M, Cormio L, Azzariti A, Pagliarulo A: The interaction of celecoxib with MDR transporters enhances the activity of mitomycin C in a bladder cancer cell line. Mol Cancer. 2013 May 24;12:47. doi: 10.1186/1476-4598-12-47. [PubMed:23705854]

Drug created on June 13, 2005 07:24 / Updated on October 15, 2019 18:55