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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/24 08:25:26」(JST)

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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) including ibuprofen and naprosyn. However, in the United States ketorolac is the only injectable NSAID, although it is banned in many European countries due to concerns about surgical bleeding and stomach ulcers after surgery.

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.^[1] 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.^[2]^[3]

References

^ Health Canada Endorsed Important Safety Information on Valdecoxib Tablets, A Selective Cyclo-oxygenase-2 (COX-2) Inhibitor Non-Steroidal Anti-Inflammatory Drug (NSAID), April 21, 2005
^ Gajraj N. M. (2007). "COX-2 inhibitors celecoxib and parecoxib: valuable options for postoperative pain management". Curr Top Med Chem 7 (3): 235–49.
^ Kiehl, S (March 13, 2005), "Secrecy on the Rise", The Baltimore Sun

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1. COX-2阻害剤および胃十二指腸障害：大規模臨床試験 cox 2 inhibitors and gastroduodenal toxicity major clinical trials
2. COX-2選択的阻害剤：有害な心血管系への影響 cox 2 selective inhibitors adverse cardiovascular effects
3. COX-2選択的阻害剤の概要 overview of selective cox 2 inhibitors
4. Management of acute perioperative pain
5. 非ステロイド性抗炎症剤（NSAIDs）（アスピリンを含む）：アレルギー反応および偽アレルギー反応 nsaids including aspirin allergic and pseudoallergic reactions

English Journal

Erratum to: Parecoxib Added to Ropivacaine Prolongs Duration of Axillary Brachial Plexus Blockade and Relieves Postoperative Pain.

Liu X, Zhao X, Lou J, Wang Y, Shen X.SourceDepartment of Anesthesiology, Xinhua Hospital, Shanghai Jiaotong University School of Medicine, 200092, Shanghai, China.
Clinical orthopaedics and related research.Clin Orthop Relat Res.2012 Dec 14. [Epub ahead of print]
PMID 23242827

Parecoxib Added to Ropivacaine Prolongs Duration of Axillary Brachial Plexus Blockade and Relieves Postoperative Pain.

Liu X, Zhao X, Lou J, Wang Y, Shen X.SourceDepartment of Anesthesiology, Xinhua Hospital, Shanghai Jiaotong University School of Medicine, 200092, Shanghai, China.
Clinical orthopaedics and related research.Clin Orthop Relat Res.2012 Nov 21. [Epub ahead of print]
BACKGROUND: Cyclooxygenase (COX)-2 antagonist is widely used for intravenous postoperative pain relief. Recent studies reported COX-2 in the spinal dorsal horn could modulate spinal nociceptive processes. Epidural parecoxib in rats showed no neurotoxicity. These findings suggested applying a COX-2 a
PMID 23179117

Japanese Journal

Complications of the COX-2 inhibitors parecoxib and valdecoxib after cardiac surgery

NUSSMEIER NA
N Engl J Med 352(11), 1081-1091, 2005
NAID 30022562053

Selective cyclo-oxygenase-2 inhibition with parecoxib acutely impairs endothelium-dependent vasodilatation in patients with essential hypertension

BULUT D
J Hypertens 21, 1663-1667, 2003
NAID 30018867808

The influence of parecoxib, a parenteral cyclooxygenase-2 specific inhibitor, on the pharmacokinetics and clinical effects of midazolam

IBRAHIM A
Anesth Analg. 95, 667-673, 2002
NAID 30012758581

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「パレコキシブ」

Parecoxib
Systematic (IUPAC) name
	N-{[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]; sulfonyl}propanamide
Clinical data
AHFS/Drugs.com	International Drug Names
License data	EU EMA: Dynastat;
Pregnancy; category	Not recommended;
Routes of; administration	Intravenous and intramuscular
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	100%
Protein binding	98%
Metabolism	Hepatic to valdecoxib and propionic acid; CYP extensively involved (mainly CYP3A4 and 2C9)
Biological half-life	22 minutes (parecoxib); 8 hours (valdecoxib)
Excretion	Renal (70%, metabolites)
Identifiers
CAS Number	202409-33-4
ATC code	M01AH04 (WHO)
PubChem	CID 119828
IUPHAR/BPS	2895
DrugBank	DB08439
ChemSpider	106990
UNII	9TUW81Y3CE
ChEBI	CHEBI:73038
ChEMBL	CHEMBL1206690
Chemical data
Formula	C19H18N2O4S
Molar mass	370.422 g/mol
	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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英: parecoxib

コキシブ系非ステロイド性抗炎症薬;COX-2選択的阻害

[1] Health Canada Endorsed Important Safety Information on Valdecoxib Tablets, A Selective Cyclo-oxygenase-2 (COX-2) Inhibitor Non-Steroidal Anti-Inflammatory Drug (NSAID), April 21, 2005

[2] Gajraj N. M. (2007). "COX-2 inhibitors celecoxib and parecoxib: valuable options for postoperative pain management". Curr Top Med Chem 7 (3): 235–49.

[baltimoresun_2005-3] Kiehl, S (March 13, 2005), "Secrecy on the Rise", The Baltimore Sun

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parecoxib