parecoxib   Click here for help

GtoPdb Ligand ID: 2895

Synonyms: Dynastat® | SC-69124
Approved drug PDB Ligand Immunopharmacology Ligand
parecoxib is an approved drug (UK (2002), EMA (2009))
Compound class: Synthetic organic
Comment: The brand Dynastat® contains parecoxib sodium (PubChem CID 15895902). Parecoxib is a water soluble prodrug of valdecoxib, a non‑steroidal anti‑inflammatory drug (NSAID).
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 97.65
Molecular weight 370.1
XLogP 3.68
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCC(=O)NS(=O)(=O)c1ccc(cc1)c1c(C)onc1c1ccccc1
Isomeric SMILES CCC(=O)NS(=O)(=O)c1ccc(cc1)c1c(C)onc1c1ccccc1
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)
InChI Key TZRHLKRLEZJVIJ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Non-steroidal anti-inflammatory ligands
Approved drug? Yes (UK (2002), EMA (2009))
Is prodrug? Yes
Active form valdecoxib
IUPAC Name Click here for help
N-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylpropanamide
International Nonproprietary Names Click here for help
INN number INN
7816 parecoxib
Synonyms Click here for help
Dynastat® | SC-69124
Database Links Click here for help
CAS Registry No. 198470-84-7 (source: Scifinder)
ChEMBL Ligand CHEMBL1206690
DrugBank Ligand DB08439
DrugCentral Ligand 2063
GtoPdb PubChem SID 178100244
PubChem CID 119828
RCSB PDB Ligand PXB
Search Google for chemical match using the InChIKey TZRHLKRLEZJVIJ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone TZRHLKRLEZJVIJ
Search PubMed clinical trials parecoxib
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UniChem Compound Search for chemical match using the InChIKey TZRHLKRLEZJVIJ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey TZRHLKRLEZJVIJ-UHFFFAOYSA-N
Wikipedia Parecoxib