Identification
- Summary
Parecoxib is a selective COX-2 inhibitor and NSAID used for the short-term management of perioperative pain.
- Brand Names
- Dynastat
- Generic Name
- Parecoxib
- DrugBank Accession Number
- DB08439
- Background
Parecoxib is a water-soluble and injectable prodrug of valdecoxib. It is marketed as Dynastat in the European Union. Parecoxib is a COX2 selective inhibitor in the same category as celecoxib (Celebrex) and rofecoxib (Vioxx). As it is injectable, it can be used perioperatively when patients are unable to take oral medications. It is approved through much of Europe for short term perioperative pain control much in the same way ketorolac (Toradol) is used in the United States. A letter of non-approval for parecoxib was issued by the FDA in 2005.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Parecoxib (DB08439)
- Weight
- Average: 370.422
Monoisotopic: 370.098727764 - Chemical Formula
- C19H18N2O4S
- Synonyms
- N-((p-(5-methyl-3-phenyl-4-isoxazolyl)phenyl)sulfonyl)propionamide
- Parecoxib
- Parécoxib
- Parecoxibum
- External IDs
- SC 69124
- SC-69124
Pharmacology
- Indication
Used for short term perioperative pain control.
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 Treatment of Post-operative pain •••••••••••• - 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
Not Available
- Mechanism of action
Target Actions Organism AProstaglandin G/H synthase 2 inhibitorHumans ULactotransferrin Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
98%
- Metabolism
Hepatic. Metabolized primarily via CYP3A4 and 2C9 to valdecoxib and propionic acid.
- Route of elimination
Not Available
- Half-life
22 minutes (parecoxib); 8 hours (valdecoxib)
- Clearance
Not Available
- 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
Not Available
- Pathways
- Not Available
- 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 Parecoxib may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Parecoxib can be increased when it is combined with Abametapir. Abatacept The metabolism of Parecoxib can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Parecoxib is combined with Abciximab. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Parecoxib. - Food Interactions
- No interactions found.
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.- Product Ingredients
Ingredient UNII CAS InChI Key Parecoxib sodium EB87433V6F 198470-85-8 HQPVVKXJNZEAFW-UHFFFAOYSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dynastat Injection, powder, for solution 40 mg Intramuscular; Intravenous Pfizer Europe Ma Eeig 2016-10-11 Not applicable EU 
Dynastat Injection, powder, for solution 40 mg Intramuscular; Intravenous Pfizer Europe Ma Eeig 2016-10-11 Not applicable EU Dynastat Injection, powder, for solution 40 mg Intramuscular; Intravenous Pfizer Europe Ma Eeig 2016-10-11 Not applicable EU Dynastat Injection, powder, for solution 40 mg Intramuscular; Intravenous Pfizer Europe Ma Eeig 2016-10-11 Not applicable EU Parecoxib Sodium Injection, powder, for solution 40 mg/1 Intramuscular; Intravenous Pharmacia and Upjohn Company LLC 2013-04-01 Not applicable US 
Categories
- ATC Codes
- M01AH04 — Parecoxib
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antirheumatic Agents
- COX-2 Inhibitors
- Cyclooxygenase Inhibitors
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Musculo-Skeletal System
- Nephrotoxic agents
- Peripheral Nervous System Agents
- Selective Cyclooxygenase 2 Inhibitors (NSAIDs)
- Sensory System Agents
- 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 / Sulfonyls / Organosulfonic acids and derivatives / Isoxazoles / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds show 2 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenesulfonamide / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative / Isoxazole / Organic nitrogen compound / Organic oxide show 10 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfonamide, isoxazoles (CHEBI:73038)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 9TUW81Y3CE
- CAS number
- 198470-84-7
- InChI Key
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H18N2O4S/c1-3-17(22)21-26(23,24)16-11-9-14(10-12-16)18-13(2)25-20-19(18)15-7-5-4-6-8-15/h4-12H,3H2,1-2H3,(H,21,22)
- IUPAC Name
- N-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonyl]propanamide
- SMILES
- CCC(=O)NS(=O)(=O)C1=CC=C(C=C1)C1=C(C)ON=C1C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D02709
- PubChem Compound
- 119828
- PubChem Substance
- 99444910
- ChemSpider
- 106990
- 279950
- ChEBI
- 73038
- ChEMBL
- CHEMBL1206690
- ZINC
- ZINC000005761797
- PharmGKB
- PA166049193
- PDBe Ligand
- PXB
- Wikipedia
- Parecoxib
- PDB Entries
- 2zmb
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 Basic Science Secondary Hyperalgesia 1 4 Completed Prevention Postoperative pain 1 4 Completed Prevention Postoperative Pain Management, Pain Threshold, Shoulder Pain, Laparoscopies 1 4 Completed Supportive Care Postoperative pain 1 4 Completed Treatment Acute Renal Colic / Ureteric Stones 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for solution Intramuscular; Intravenous 40 mg Solution Parenteral 40.000 mg Powder 40 mg/1vial Injection, powder, lyophilized, for solution Intramuscular; Intravenous 40 mg Injection Powder 40 mg Injection, powder, for solution Intramuscular; Intravenous 40 mg/1 Injection, powder, for solution Intramuscular - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0162 mg/mL ALOGPS logP 3.42 ALOGPS logP 3.51 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 4.24 Chemaxon pKa (Strongest Basic) 0.42 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 89.27 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 98.9 m3·mol-1 Chemaxon Polarizability 38 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 + 0.8694 Caco-2 permeable - 0.644 P-glycoprotein substrate Non-substrate 0.8144 P-glycoprotein inhibitor I Non-inhibitor 0.7995 P-glycoprotein inhibitor II Non-inhibitor 0.8537 Renal organic cation transporter Non-inhibitor 0.8889 CYP450 2C9 substrate Non-substrate 0.702 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Non-substrate 0.6159 CYP450 1A2 substrate Non-inhibitor 0.8459 CYP450 2C9 inhibitor Inhibitor 0.801 CYP450 2D6 inhibitor Non-inhibitor 0.8356 CYP450 2C19 inhibitor Inhibitor 0.6608 CYP450 3A4 inhibitor Non-inhibitor 0.5165 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8722 Ames test Non AMES toxic 0.7504 Carcinogenicity Carcinogens 0.5086 Biodegradation Not ready biodegradable 0.9899 Rat acute toxicity 2.2665 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9874 hERG inhibition (predictor II) Non-inhibitor 0.9083
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0094000000-141a6f7c103c3f95f9cd Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03xr-0009000000-4932556610cd0a6084c7 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-1094000000-7a45a6bb80bee99b4862 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03xs-0049000000-0401bbf897d3e5bd94f5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fsl-5693000000-e881f923299da76e813a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01ox-6095000000-3ac2641ebd2656ce4116 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 197.6665416 predictedDarkChem Lite v0.1.0 [M-H]- 182.99579 predictedDeepCCS 1.0 (2019) [M+H]+ 198.5035416 predictedDarkChem Lite v0.1.0 [M+H]+ 185.35379 predictedDeepCCS 1.0 (2019) [M+Na]+ 197.9036416 predictedDarkChem Lite v0.1.0 [M+Na]+ 192.37807 predictedDeepCCS 1.0 (2019)
Targets
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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, Bertenshaw SR, Brown DL, Carter JS, Graneto MJ, Kellogg MS, Koboldt CM, Yuan J, Zhang YY, Seibert K: N-[[(5-methyl-3-phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium: A potent and selective inhibitor of COX-2 for parenteral administration. J Med Chem. 2000 May 4;43(9):1661-3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serine-type endopeptidase activity
- Specific Function
- Transferrins are iron binding transport proteins which can bind two Fe(3+) ions in association with the binding of an anion, usually bicarbonate.Lactotransferrin is a major iron-binding and multifu...
- Gene Name
- LTF
- Uniprot ID
- P02788
- Uniprot Name
- Lactotransferrin
- Molecular Weight
- 78181.225 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
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
- 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]
- EMA Summary of Product Characteristics: Dynastat (parecoxib) oral tablets [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
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- EMA Summary of Product Characteristics: Dynastat (parecoxib) oral tablets [Link]
Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52