Identification
- Summary
Valdecoxib is a COX-2 inhibitor used to treat osteoarthritis and dysmenorrhoea.
- Brand Names
- Bextra
- Generic Name
- Valdecoxib
- DrugBank Accession Number
- DB00580
- Background
Valdecoxib was removed from the Canadian, U.S., and E.U. markets in 2005 due to concerns about a possible increased risk of heart attack and stroke.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
Structure for Valdecoxib (DB00580)
- Weight
- Average: 314.359
Monoisotopic: 314.072513014 - Chemical Formula
- C16H14N2O3S
- Synonyms
- Valdecoxib
Pharmacology
- Indication
For the treatment of osteoarthritis and dysmenorrhoea
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Osteoarthritis (oa) •••••••••••• •••••• Treatment of Primary dysmenorrhoea •••••••••••• •••••• Symptomatic treatment of Rheumatoid arthritis •••••••••••• ••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Valdecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). Valdecoxib is used for its anti-inflammatory, analgesic, and antipyretic activities in the management of osteoarthritis (OA) and for the treatment of dysmenorrhea or acute pain. Unlike celecoxib, valdecoxib lacks a sulfonamide chain and does not require CYP450 enzymes for metabolism.
- Mechanism of action
Both COX-1 and COX-2 catalyze the conversion of arachidonic acid to prostaglandin (PG) H2, the precursor of PGs and thromboxane. Valdecoxib selectively inhibits the cyclooxygenase-2 (COX-2) enzyme, important for the mediation of inflammation and pain. Unlike non-selective NSAIDs, valdecoxib does not inhibit platelet aggregation.
Target Actions Organism AProstaglandin G/H synthase 2 inhibitorHumans UCarbonic anhydrase 2 inhibitorHumans UCarbonic anhydrase 3 inhibitorHumans - Absorption
Oral bioavailability is 83%.
- Volume of distribution
- 86 L
- Protein binding
98%
- Metabolism
Hepatic (involves CYP3A4 and 2C9)
Hover over products below to view reaction partners
- Route of elimination
Valdecoxib is eliminated predominantly via hepatic metabolism with less than 5% of the dose excreted unchanged in the urine and feces. About 70% of the dose is excreted in the urine as metabolites, and about 20% as valdecoxib N-glucuronide.
- Half-life
8-11 hours
- Clearance
- oral cl=6 L/h
- 6 – 7 L/h [In patients undergoing hemodialysis]
- 6 – 7 L/h [healthy elderly subjects]
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms following acute NSAID overdoses are usually limited to lethargy, drowsiness, nausea, vomiting, and epigastric pain, which are generally reversible with supportive care. Gastrointestinal bleeding can occur. Hypertension, acute renal failure, respiratory depression and coma may occur, but are rare.
- Pathways
Pathway Category Valdecoxib Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Valdecoxib may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Valdecoxib can be increased when it is combined with Abametapir. Abatacept The metabolism of Valdecoxib can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Valdecoxib is combined with Abciximab. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Valdecoxib. - Food Interactions
- Avoid alcohol. Ingesting alcohol may increase the risk of gastrointestinal bleeding.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bextra Tablet, film coated 20 mg/1 Oral G.D. Searle LLC 2006-02-06 Not applicable US 
Bextra Tablet, film coated 20 mg/1 Oral Physicians Total Care, Inc. 2002-04-30 2005-07-31 US Bextra Tablet, film coated 10 mg/1 Oral G.D. Searle LLC 2006-02-06 Not applicable US Bextra Tablet, film coated 10 mg/1 Oral Physicians Total Care, Inc. 2001-11-16 2005-07-31 US
Categories
- ATC Codes
- M01AH03 — Valdecoxib
- M01AH — Coxibs
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Amides
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antirheumatic Agents
- Benzene Derivatives
- COX-2 Inhibitors
- Cyclooxygenase Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (weak)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Musculo-Skeletal System
- Nephrotoxic agents
- Peripheral Nervous System Agents
- Selective Cyclooxygenase 2 Inhibitors (NSAIDs)
- Sensory System Agents
- Sulfonamides
- Sulfones
- Sulfur Compounds
- UGT1A9 Substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonamides
- Direct Parent
- Benzenesulfonamides
- Alternative Parents
- Benzenesulfonyl compounds / Organosulfonamides / Isoxazoles / Heteroaromatic compounds / Aminosulfonyl compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds show 2 more
- Substituents
- Aminosulfonyl compound / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenesulfonamide / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative / Isoxazole / Organic nitrogen compound show 12 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfonamide, isoxazoles (CHEBI:63634)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 2919279Q3W
- CAS number
- 181695-72-7
- InChI Key
- LNPDTQAFDNKSHK-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
- IUPAC Name
- 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide
- SMILES
- CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O
References
- Synthesis Reference
Eswaraiah Sajja, Anumula Reddy, Aalla Sampath, Gilla Goverdhan, "Process for preparing crystalline form A of valdecoxib." U.S. Patent US20050272787, issued December 08, 2005.
US20050272787- General References
- FDA Approved Drug Products: Betra (valdecoxib) oral tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0005033
- PubChem Compound
- 119607
- PubChem Substance
- 46506229
- ChemSpider
- 106796
- BindingDB
- 13063
- 278567
- ChEBI
- 63634
- ChEMBL
- CHEMBL865
- ZINC
- ZINC000000006694
- Therapeutic Targets Database
- DAP001541
- PharmGKB
- PA10226
- PDBe Ligand
- COX
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Valdecoxib
- PDB Entries
- 2aw1
- FDA label
- Download (82.8 KB)
- MSDS
- Download (70.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Hyperalgesia / Pain 1 4 Completed Treatment Back Pain Lower Back 1 4 Completed Treatment Menstrual Distress (Dysmenorrhea) 1 4 Completed Treatment Neurosurgery / Pain 1 4 Completed Treatment Pain / Sprains / Sprains and Strains 1
Pharmacoeconomics
- Manufacturers
- Gd searle llc
- Packagers
- Cardinal Health
- GD Searle LLC
- Murfreesboro Pharmaceutical Nursing Supply
- PD-Rx Pharmaceuticals Inc.
- Pfizer Inc.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Tablet, film coated Oral Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 20 mg/1 Tablet, coated Oral 40 mg Tablet, film coated Oral 10 mg Tablet, coated Oral 20 mg Tablet Oral 20 mg Tablet Oral 40 mg Tablet, film coated Oral 40 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7135489 No 2006-11-14 2017-08-12 US US5633272 No 1997-05-27 2015-02-13 US CA2212836 No 2003-08-12 2016-02-12 Canada 
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 3.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0348 mg/mL ALOGPS logP 3.32 ALOGPS logP 2.82 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 10.06 Chemaxon pKa (Strongest Basic) 0.42 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 86.19 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 84.71 m3·mol-1 Chemaxon Polarizability 31.76 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9386 Caco-2 permeable + 0.5 P-glycoprotein substrate Non-substrate 0.8864 P-glycoprotein inhibitor I Non-inhibitor 0.8772 P-glycoprotein inhibitor II Non-inhibitor 0.9157 Renal organic cation transporter Non-inhibitor 0.8576 CYP450 2C9 substrate Non-substrate 0.7356 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Non-substrate 0.6501 CYP450 1A2 substrate Non-inhibitor 0.5759 CYP450 2C9 inhibitor Inhibitor 0.5385 CYP450 2D6 inhibitor Non-inhibitor 0.8875 CYP450 2C19 inhibitor Inhibitor 0.5958 CYP450 3A4 inhibitor Non-inhibitor 0.8652 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7649 Ames test Non AMES toxic 0.8277 Carcinogenicity Non-carcinogens 0.7399 Biodegradation Not ready biodegradable 0.9948 Rat acute toxicity 2.0680 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9708 hERG inhibition (predictor II) Non-inhibitor 0.8652
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.4014465 predictedDarkChem Lite v0.1.0 [M-H]- 182.1885465 predictedDarkChem Lite v0.1.0 [M-H]- 170.29338 predictedDeepCCS 1.0 (2019) [M+H]+ 183.9061465 predictedDarkChem Lite v0.1.0 [M+H]+ 182.6029465 predictedDarkChem Lite v0.1.0 [M+H]+ 172.65138 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.2634465 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.6475465 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.91544 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Talley JJ, Brown DL, Carter JS, Graneto MJ, Koboldt CM, Masferrer JL, Perkins WE, Rogers RS, Shaffer AF, Zhang YY, Zweifel BS, Seibert K: 4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. J Med Chem. 2000 Mar 9;43(5):775-7. [Article]
- Jain KK: Evaluation of intravenous parecoxib for the relief of acute post-surgical pain. Expert Opin Investig Drugs. 2000 Nov;9(11):2717-23. [Article]
- Yuan JJ, Yang DC, Zhang JY, Bible R Jr, Karim A, Findlay JW: Disposition of a specific cyclooxygenase-2 inhibitor, valdecoxib, in human. Drug Metab Dispos. 2002 Sep;30(9):1013-21. [Article]
- Tacconelli S, Capone ML, Sciulli MG, Ricciotti E, Patrignani P: The biochemical selectivity of novel COX-2 inhibitors in whole blood assays of COX-isozyme activity. Curr Med Res Opin. 2002;18(8):503-11. [Article]
- Hood WF, Gierse JK, Isakson PC, Kiefer JR, Kurumbail RG, Seibert K, Monahan JB: Characterization of celecoxib and valdecoxib binding to cyclooxygenase. Mol Pharmacol. 2003 Apr;63(4):870-7. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Gierse JK, Zhang Y, Hood WF, Walker MC, Trigg JS, Maziasz TJ, Koboldt CM, Muhammad JL, Zweifel BS, Masferrer JL, Isakson PC, Seibert K: Valdecoxib: assessment of cyclooxygenase-2 potency and selectivity. J Pharmacol Exp Ther. 2005 Mar;312(3):1206-12. Epub 2004 Oct 19. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Agundez JA, Garcia-Martin E, Martinez C: Genetically based impairment in CYP2C8- and CYP2C9-dependent NSAID metabolism as a risk factor for gastrointestinal bleeding: is a combination of pharmacogenomics and metabolomics required to improve personalized medicine? Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):607-20. doi: 10.1517/17425250902970998 . [Article]
- Valdexocib FDA label [File]
- EMA public statement: Valdecoxib [File]
- 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
- 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. [Article]
- Ibrahim AE, Feldman J, Karim A, Kharasch ED: Simultaneous assessment of drug interactions with low- and high-extraction opioids: application to parecoxib effects on the pharmacokinetics and pharmacodynamics of fentanyl and alfentanil. Anesthesiology. 2003 Apr;98(4):853-61. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:52