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Identification
NameParecoxib
Accession NumberDB08439
TypeSmall Molecule
GroupsApproved
Description

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. In 2005, the U.S. Food and Drug Administration (FDA) issued a letter of non-approval for parecoxib in the United States.

Structure
Thumb
SynonymsNot Available
External Identifiers
  • SC 69124
  • SC-69124
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DynastatNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII9TUW81Y3CE
CAS number198470-84-7
WeightAverage: 370.422
Monoisotopic: 370.098727764
Chemical FormulaC19H18N2O4S
InChI KeyTZRHLKRLEZJVIJ-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Oxazole
  • Isoxazole
  • Azole
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed for short term perioperative pain control.
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding98%
Metabolism

Hepatic. Metabolized primarily via CYP3A4 and 2C9 to valdecoxib and propionic acid.

Route of eliminationNot Available
Half life22 minutes (parecoxib); 8 hours (valdecoxib)
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesM01AH04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AtazanavirThe serum concentration of Parecoxib can be increased when it is combined with Atazanavir.
BoceprevirThe serum concentration of Parecoxib can be increased when it is combined with Boceprevir.
CapecitabineThe serum concentration of Parecoxib can be increased when it is combined with Capecitabine.
CeritinibThe serum concentration of Parecoxib can be increased when it is combined with Ceritinib.
ClarithromycinThe serum concentration of Parecoxib can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Parecoxib can be increased when it is combined with Cobicistat.
DarunavirThe serum concentration of Parecoxib can be increased when it is combined with Darunavir.
DelavirdineThe serum concentration of Parecoxib can be increased when it is combined with Delavirdine.
DextromethorphanThe serum concentration of Dextromethorphan can be increased when it is combined with Parecoxib.
FloxuridineThe serum concentration of Parecoxib can be increased when it is combined with Floxuridine.
FluconazoleThe serum concentration of Parecoxib can be increased when it is combined with Fluconazole.
FluorouracilThe serum concentration of Parecoxib can be increased when it is combined with Fluorouracil.
GemfibrozilThe serum concentration of Parecoxib can be increased when it is combined with Gemfibrozil.
IdelalisibThe serum concentration of Parecoxib can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of Parecoxib can be increased when it is combined with Indinavir.
ItraconazoleThe serum concentration of Parecoxib can be increased when it is combined with Itraconazole.
KetoconazoleThe serum concentration of Parecoxib can be increased when it is combined with Ketoconazole.
NefazodoneThe serum concentration of Parecoxib can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Parecoxib can be increased when it is combined with Nelfinavir.
NicardipineThe serum concentration of Parecoxib can be increased when it is combined with Nicardipine.
PosaconazoleThe serum concentration of Parecoxib can be increased when it is combined with Posaconazole.
RitonavirThe serum concentration of Parecoxib can be increased when it is combined with Ritonavir.
SaquinavirThe serum concentration of Parecoxib can be increased when it is combined with Saquinavir.
SulfadiazineThe serum concentration of Parecoxib can be increased when it is combined with Sulfadiazine.
TelaprevirThe serum concentration of Parecoxib can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Parecoxib can be increased when it is combined with Telithromycin.
TolbutamideThe serum concentration of Parecoxib can be increased when it is combined with Tolbutamide.
VoriconazoleThe serum concentration of Parecoxib can be increased when it is combined with Voriconazole.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
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. [PubMed:10794682 ]
Kind
Protein
Organism
Human
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 multifunctional protein found in exocrine fluids such as breast milk and mucosal secretions. Has antimicrobial activity, which depends on the extracellular cation concentration. Antimicrobial properties incl...
Gene Name:
LTF
Uniprot ID:
P02788
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. [PubMed:10592235 ]

Enzymes

Kind
Protein
Organism
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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. [PubMed:12657846 ]
  2. DrugBank Entry Valdecoxib (is a prodrug of Valdecoxib) [Link]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. DrugBank Entry Valdecoxib (is a prodrug of Valdecoxib) [Link]
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Drug created on September 15, 2010 15:31 / Updated on October 21, 2015 10:50