parecoxib (CED0005395)

Record Information

Version

1.0

Creation Date

2016-06-03 11:54:44 UTC

Update Date

2026-08-20 02:29:44 UTC

Accession Number

CHEM044242

Identification

Common Name

parecoxib

Class

Small Molecule

Description

Parecoxib is an organic compound with the formula C19H18N2O4S and an average molecular weight of 370.42 g/mol. It belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. This compound is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically those categorized as antiinflammatory and antirheumatic products. Recorded exposure routes for parecoxib include intramuscular, intravenous, and parenteral administration. In terms of biological activity, parecoxib acts on two recorded protein targets. It functions as an inhibitor of Lactotransferrin (LTF) and Prostaglandin G/H synthase 2 (PTGS2).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-((p-(5-Methyl-3-phenyl-4-isoxazolyl)phenyl)sulfonyl)propionamide	ChEBI
Parecoxibum	ChEBI
SC 69124	ChEBI
SC-69124	ChEBI
N-((p-(5-Methyl-3-phenyl-4-isoxazolyl)phenyl)sulphonyl)propionamide	Generator
N-(((5-Methyl-3-phenylisoxazol-4-yl)-phenyl)sulfonyl)propanamine, sodium salt	MeSH
Parecoxib sodium	MeSH
N-(((5-Methyl-3-phenylisoxazol-4-yl)-phenyl)sulfonyl)propanamide	MeSH
Dynastat	MeSH
N-(((Me-P)-P)S)P	MeSH

Chemical Formula

C₁₉H₁₈N₂O₄S

Average Molecular Mass

370.422 g/mol

Monoisotopic Mass

370.099 g/mol

CAS Registry Number

198470-84-7

IUPAC Name

N-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonyl]propanamide

Traditional Name

parecoxib

SMILES

CCC(=O)NS(=O)(=O)C1=CC=C(C=C1)C1=C(C)ON=C1C1=CC=CC=C1

InChI Identifier

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)

InChI Key

TZRHLKRLEZJVIJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Sulfonyl
Oxacycle
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:73038 )
isoxazoles (CHEBI:73038 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-055b-5093000000-db3e92926f485c400d54	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0469000000-f6052003554a020d0609	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0986000000-520dd33eedc4a686c413	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-1019000000-c728be169067b0126d0d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zos-5059000000-f83fbece820e78e5eca2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0adi-8590000000-1c37127a53aae762e8de	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0009000000-0b3df646b995c3d571fc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014j-2149000000-55191fcdfab63c7101c6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f6x-7981000000-a4c6679d347cfe9d27c1	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2673.0	Log mg/kg	[1500:4800]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
363	Antiinflammatory and antirheumatic products	Healthcare, pharmaceuticals & veterinary products	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
651	Purses Money Bags Wallets	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Parecoxib Action Pathway

Parecoxib Drug Metabolism

Parecoxib Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	15.0249
Click to view 3D structure	Cytochrome c oxidase subunit 2	P00403	Humans	Predicted (SEA)	0.155698
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	60.411
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	57.5306
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	88.6703
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	42.6614
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	140.596
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	139.973
Click to view 3D structure	Matrix metalloproteinase-14	P50281	Humans	Predicted (SEA)	102.138
Click to view 3D structure	Interstitial collagenase	P03956	Humans	Predicted (SEA)	124.092
Click to view 3D structure	Collagenase 3	P45452	Humans	Predicted (SEA)	104.941
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	54.2609
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	63.6807
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	85.0114
Click to view 3D structure	Neutrophil collagenase	P22894	Humans	Predicted (SEA)	133.745
Click to view 3D structure	Carbonic anhydrase 4	Q95323	Bos taurus	Predicted (SEA)	43.1285
Click to view 3D structure	Macrophage metalloelastase	P39900	Humans	Predicted (SEA)	88.4367
Click to view 3D structure	Stromelysin-1	P08254	Humans	Predicted (SEA)	122.69
Click to view 3D structure	Carbonic anhydrase 4	P22748	Humans	Predicted (SEA)	66.4054
Click to view 3D structure	Carbonic anhydrase	Q5AJ71	Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Predicted (SEA)	35.11
Click to view 3D structure	PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)	P96878	Mycobacterium tuberculosis	Predicted (SEA)	32.6967
Click to view 3D structure	Matrilysin	P09237	Humans	Predicted (SEA)	127.751
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	64.537
Click to view 3D structure	Leucine--tRNA ligase	Q2FXH2	Staphylococcus aureus (strain NCTC 8325)	Predicted (SEA)	7.16213
Click to view 3D structure	Carbonic anhydrase 13	Q8N1Q1	Humans	Predicted (SEA)	35.1878