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Parecoxib Antipyretic Analgesics Drugs Parecoxib Powder CAS 198470-84-7

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Parecoxib Antipyretic Analgesics Drugs Parecoxib Powder CAS 198470-84-7

Large Image :  Parecoxib Antipyretic Analgesics Drugs Parecoxib Powder CAS 198470-84-7

Product Details:

Place of Origin: China
Brand Name: R&M
Certification: ISO 9001, USP, GMP
Model Number: 01

Payment & Shipping Terms:

Minimum Order Quantity: 1g
Price: negotiation
Packaging Details: vaccum packing of aluminum foil bag
Detailed Product Description
Cas: 198470-84-7 Name: Parecoxib
Appearance: White Powder Formula: C19H18N2O4S
PackAge: Standard Or As Customer's Require Storage: Store The Shade

Parecoxib Antipyretic Analgesics Drugs Parecoxib Powder CAS 198470-84-7

 

 

Parecoxib

Clinical data
AHFS/Drugs.com International Drug Names
License data
  • EU EMA: by INN

Pregnancy
category
  • Not recommended
Routes of
administration
Intravenous andintramuscular
ATC code
  • M01AH04 (WHO)

Legal status
Legal status
  • AU: S4 (Prescription only)
    UK: POM (Prescription only)

Pharmacokinetic data
Bioavailability 100%
Protein binding 98%
Metabolism Hepatic to valdecoxib andpropionic acid
CYP extensively involved (mainly CYP3A4 and 2C9)
Eliminationhalf-life 22 minutes (parecoxib)
8 hours (valdecoxib)
Excretion Renal (70%, metabolites)
Identifiers
IUPAC name[hide]
  • N-{[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]
    sulfonyl}propanamide
CAS Number
  • 198470-84-7 [Yes]

PubChem CID
  • 119828

IUPHAR/BPS
  • 2895

DrugBank
  • DB08439 [Yes]

ChemSpider
  • 106990 [Yes]

UNII
  • 9TUW81Y3CE

ChEBI
  • CHEBI:73038 [No]

ChEMBL
  • CHEMBL1206690 [No]

ECHA InfoCard 100.230.078 [Edit this at Wikidata]
Chemical and physical data
Formula C19H18N2O4S
Molar mass 370.422 g/mol
3D model (JSmol)
  • Interactive image

SMILES[hide]
  • O=C(NS(=O)(=O)c3ccc(c2c(onc2c1ccccc1)C)cc3)CC
InChI[hide]
  • 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

 

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. However, unlike ketorolac, parecoxib has no effect on platelet function and therefore does not promote bleeding during or after surgery. In addition, ketorolac has a much higher gastrointestinal toxicity profile compared to most other nonsteroidal antiinflammatory drugs (NSAIDs) includingibuprofen and naproxen. While banned in many European countries due to concerns about surgical bleeding and stomach ulcers after surgery, ketorolac is the only injectable NSAID 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. No reasons were ever documented publicly for the non-approval, although one study noted increased occurrences of heart attacks following cardiac bypass surgery compared to placebo when high doses of parecoxib were used to control pain after surgery. It is also important to remember that rare but severe allergic reactions (Stevens-Johnson Syndrome, Lyell syndrome) have been described with valdecoxib, the molecule to which parecoxib is converted. 

 

The drug is not approved for use after cardiac surgery in Europe. Ketorolac, still banned in much of Europe, and IV ibuprofen are therefore the only options for IV NSAIDs in the United States, and it is not clear whether parecoxib will be resubmitted to the FDA in the future.

 

All anti-inflammatory medications in the U.S. carry the same warning regarding skin reactions, and none are approved for use during CABG surgery, so the reason for the FDA denying the approval of parecoxib remains unknown, but was likely related to political pressure from the US Congress to not approve another COX-2 selective inhibitor in the wake of the Vioxx affair. No COX-2 selective inhibitor has been approved in the US since that time, regardless of the safety profile of parecoxib in Europe. Efforts to find out the scientific rationale, or more likely the lack thereof, that the FDA used to justify the non-approval of parecoxib in the USA have proven futile due to secrecy issues.

 

The political motivation to not approve parecoxib was further supported by a 2017 pooled analysis of safety data in 28 published studies, which showed after 69,567,300 units of parecoxib, skin rash and cardiac complications were minimal, if at all, different from placebo.

 

Parecoxib, along with other COX-2 selective inhibitors, celecoxib, valdecoxib, and mavacoxib, were discovered by a team at the Searle division of Monsanto led by John Talley.

 

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