Parecoxib

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofPost-operative pain••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Humans
ULactotransferrinNot AvailableHumans
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

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
AbacavirParecoxib may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Parecoxib can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Parecoxib can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Parecoxib is combined with Abciximab.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Parecoxib.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Parecoxib sodiumEB87433V6F198470-85-8HQPVVKXJNZEAFW-UHFFFAOYSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DynastatInjection, powder, for solution40 mgIntramuscular; IntravenousPfizer Europe Ma Eeig2016-10-11Not applicableEU flag
DynastatInjection, powder, for solution40 mgIntramuscular; IntravenousPfizer Europe Ma Eeig2016-10-11Not applicableEU flag
DynastatInjection, powder, for solution40 mgIntramuscular; IntravenousPfizer Europe Ma Eeig2016-10-11Not applicableEU flag
DynastatInjection, powder, for solution40 mgIntramuscular; IntravenousPfizer Europe Ma Eeig2016-10-11Not applicableEU flag
Parecoxib SodiumInjection, powder, for solution40 mg/1Intramuscular; IntravenousPharmacia and Upjohn Company LLC2013-04-01Not applicableUS flag

Categories

ATC Codes
M01AH04 — Parecoxib
Drug Categories
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
KEGG Drug
D02709
PubChem Compound
119828
PubChem Substance
99444910
ChemSpider
106990
RxNav
279950
ChEBI
73038
ChEMBL
CHEMBL1206690
ZINC
ZINC000005761797
PharmGKB
PA166049193
PDBe Ligand
PXB
Wikipedia
Parecoxib
PDB Entries
2zmb

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceSecondary Hyperalgesia1
4CompletedPreventionPostoperative pain1
4CompletedPreventionPostoperative Pain Management, Pain Threshold, Shoulder Pain, Laparoscopies1
4CompletedSupportive CarePostoperative pain1
4CompletedTreatmentAcute Renal Colic / Ureteric Stones1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionIntramuscular; Intravenous40 mg
SolutionParenteral40.000 mg
Powder40 mg/1vial
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous40 mg
Injection
Powder40 mg
Injection, powder, for solutionIntramuscular; Intravenous40 mg/1
Injection, powder, for solutionIntramuscular
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0162 mg/mLALOGPS
logP3.42ALOGPS
logP3.51Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.24Chemaxon
pKa (Strongest Basic)0.42Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area89.27 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity98.9 m3·mol-1Chemaxon
Polarizability38 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+0.8694
Caco-2 permeable-0.644
P-glycoprotein substrateNon-substrate0.8144
P-glycoprotein inhibitor INon-inhibitor0.7995
P-glycoprotein inhibitor IINon-inhibitor0.8537
Renal organic cation transporterNon-inhibitor0.8889
CYP450 2C9 substrateNon-substrate0.702
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.6159
CYP450 1A2 substrateNon-inhibitor0.8459
CYP450 2C9 inhibitorInhibitor0.801
CYP450 2D6 inhibitorNon-inhibitor0.8356
CYP450 2C19 inhibitorInhibitor0.6608
CYP450 3A4 inhibitorNon-inhibitor0.5165
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8722
Ames testNon AMES toxic0.7504
CarcinogenicityCarcinogens 0.5086
BiodegradationNot ready biodegradable0.9899
Rat acute toxicity2.2665 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9874
hERG inhibition (predictor II)Non-inhibitor0.9083
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0094000000-141a6f7c103c3f95f9cd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xr-0009000000-4932556610cd0a6084c7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1094000000-7a45a6bb80bee99b4862
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xs-0049000000-0401bbf897d3e5bd94f5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fsl-5693000000-e881f923299da76e813a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-6095000000-3ac2641ebd2656ce4116
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-197.6665416
predicted
DarkChem Lite v0.1.0
[M-H]-182.99579
predicted
DeepCCS 1.0 (2019)
[M+H]+198.5035416
predicted
DarkChem Lite v0.1.0
[M+H]+185.35379
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.9036416
predicted
DarkChem Lite v0.1.0
[M+Na]+192.37807
predicted
DeepCCS 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
  1. 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
  1. 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
  1. 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]
  2. 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
  1. 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