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| Clinical data | |
|---|---|
| AHFS/Drugs.com | International Drug Names |
| Pregnancy category |
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| Routes of administration | Intravenous,intramuscular |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | 100% |
| Protein binding | 98% |
| Metabolism | Liver tovaldecoxib andpropionic acid CYP extensively involved (mainlyCYP3A4 and2C9) |
| Eliminationhalf-life | 22 minutes (parecoxib) 8 hours (valdecoxib) |
| Excretion | Kidney (70%, metabolites) |
| Identifiers | |
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| CAS Number | |
| PubChemCID | |
| IUPHAR/BPS | |
| DrugBank |
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| ChemSpider |
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| UNII | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.230.078 |
| Chemical and physical data | |
| Formula | C19H18N2O4S |
| Molar mass | 370.42 g·mol−1 |
| 3D model (JSmol) | |
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 N Y (what is this?) (verify) | |
Parecoxib, sold under the brand nameDynastat among others, is a water-soluble andinjectableprodrug ofvaldecoxib. Parecoxib is aCOX2 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]
In 2005, the USFood 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 ofheart attacks followingcardiac bypass surgery compared to placebo when high doses of parecoxib were used to control pain after surgery. Importantly, rare but severeallergic reactions (Stevens–Johnson syndrome,Lyell syndrome) have been described withvaldecoxib, themolecule to which parecoxib is converted.[4] The drug is not approved for use after cardiac surgery in Europe.
All anti-inflammatory medications in the US 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 anotherCOX-2 selective inhibitor in the wake of theVioxx 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.[5][6]
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.[7]
Parecoxib, along with other COX-2 selective inhibitors,celecoxib,valdecoxib, andmavacoxib, were discovered by a team at theSearle division ofMonsanto led byJohn Talley.[8][9]
Parecoxib is the first parenteral COX-2 selective inhibitor available for clinical use in pain management. Its first perceptible analgesic effect occurs within seven to thirteen minutes, with clinically meaningful analgesia demonstrated within twenty-three to thirty-nine minutes and a peak effect within two hours following administration of single doses of 40 mg by IV or IM injection.[10]
| pyrazolones / pyrazolidines | |
|---|---|
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;†withdrawn drugs;‡veterinary use. | |
