Parecoxib information

Parecoxib
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: C; ;
Routes of; administration	Intravenous, intramuscular
ATC code	M01AH04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); UK: POM (Prescription only); EU: ;
Pharmacokinetic data
Bioavailability	100%
Protein binding	98%
Metabolism	Liver to valdecoxib and propionic acid; CYP extensively involved (mainly CYP3A4 and 2C9)
Elimination half-life	22 minutes (parecoxib); 8 hours (valdecoxib)
Excretion	Kidney (70%, metabolites)
Identifiers
	IUPAC name N-{[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]; sulfonyl}propanamide;
CAS Number	198470-84-7 ;
PubChem CID	119828;
IUPHAR/BPS	2895;
DrugBank	DB08439 ;
ChemSpider	106990 ;
UNII	9TUW81Y3CE;
ChEBI	CHEBI:73038 ;
ChEMBL	ChEMBL1206690 ;
CompTox Dashboard (EPA)	DTXSID1044229 ;
ECHA InfoCard	100.230.078
Chemical and physical data
Formula	C19H18N2O4S
Molar mass	370.42 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NS(=O)(=O)c3ccc(c2c(onc2c1ccccc1)C)cc3)CC;
	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) ; Key:TZRHLKRLEZJVIJ-UHFFFAOYSA-N ;
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Parecoxib, sold under the brand name Dynastat among others, is a water-soluble and injectable prodrug of valdecoxib. Parecoxib is a COX2 selective inhibitor. It is injectable. It is approved in the European Union for short term perioperative pain control.

It was patented in 1996 and approved for medical use in 2002.^[3]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ "Dynastat EPAR". European Medicines Agency. 22 March 2002. Retrieved 2 January 2024.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 522. ISBN 9783527607495.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[Dynastat_EPAR-2] "Dynastat EPAR". European Medicines Agency. 22 March 2002. Retrieved 2 January 2024.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 522. ISBN 9783527607495.

Parecoxib information

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Clinical data

AHFS/Drugs.com	International Drug Names
Pregnancy category	AU: C
Routes of administration	Intravenous, intramuscular
ATC code	M01AH04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) BR: Class C1 (Other controlled substances)^[1] UK: POM (Prescription only) EU: ^[2]
Pharmacokinetic data
Bioavailability	100%
Protein binding	98%
Metabolism	Liver to valdecoxib and propionic acid CYP extensively involved (mainly CYP3A4 and 2C9)
Elimination half-life	22 minutes (parecoxib) 8 hours (valdecoxib)
Excretion	Kidney (70%, metabolites)
Identifiers
IUPAC name N-{[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl] sulfonyl}propanamide
CAS Number	198470-84-7^Y
PubChem CID	119828
IUPHAR/BPS	2895
DrugBank	DB08439^Y
ChemSpider	106990^Y
UNII	9TUW81Y3CE
ChEBI	CHEBI:73038^N
ChEMBL	ChEMBL1206690^N
CompTox Dashboard (EPA)	DTXSID1044229
ECHA InfoCard	100.230.078
Chemical and physical data
Formula	C₁₉H₁₈N₂O₄S
Molar mass	370.42 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(NS(=O)(=O)c3ccc(c2c(onc2c1ccccc1)C)cc3)CC
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)^Y Key:TZRHLKRLEZJVIJ-UHFFFAOYSA-N^Y
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