Parecoxib

Structural formula
General
Non-proprietary name	Parecoxib
other names	N - {[4- (5-methyl-3-phenylisoxazol-4-yl) phenyl] sulfonyl} propionamide ( IUPAC )
Molecular formula	C 19 H 18 N 2 O 4 S
External identifiers / databases
EC number	803-261-6
ECHA InfoCard	100.230.078
PubChem	119828
ChemSpider	106990
DrugBank	DB08439
Wikidata	Q347941
Drug information
ATC code	M01 AH04
Drug class	COX-2 inhibitors
Mechanism of action	selective inhibition of COX-2
properties
Molar mass	370.42 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 361-373
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Parecoxib is a drug from the group of selective COX-2 inhibitors (cyclooxygenase-2 inhibitors) and is marketed by Pfizer under the trade name Dynastat . Parecoxib has not been approved in the USA due to safety concerns and has been withdrawn from the market in Switzerland. The sodium salt is used.

pharmacology

Pharmacokinetics

Parecoxib is the water-soluble and parenterally administrable prodrug of the orally administered valdecoxib (trade name: Bextra ), which was formerly marketed but discontinued . Activation takes place via enzymatic cleavage with a half-life of 22 minutes to form valdecoxib, the half-life of which as the actual active substance is approx. 8 hours, with elimination via the liver.

indication

It is approved for short-term postoperative pain therapy, preferably after dental, orthopedic and gynecological operations. Little experience is available for gastrointestinal or urological interventions. When using the device, the individual patient risk with regard to cardiovascular diseases must be weighed up.

Mechanism of action

The analgesic effect is achieved through a selective inhibition of the enzyme cyclooxygenase-2 (COX-2), with an effect occurring after approx. 7-13 minutes and the effect corresponding to an effect of 12 mg morphine , which saves opioids or opioid therapy can be avoided. It should also be noted that the substance has no effect on platelet aggregation and thus on bleeding time.

Side effects

The following side effects should be considered during treatment (selection):

increased creatinine in the blood (kidney damage)
gastroduodenal ulcer
Hypokalemia
peripheral edema
postoperative anemia
insomnia
Worsening of existing hypertension
severe cardiovascular complications

Contraindications

The following are absolute contraindications (selection):

Allergy to acetylsalicylic acid , NSAIDs or sulfonamides
inflammatory bowel disease
third trimester of pregnancy and lactation
Heart failure (NYHA II-IV)
peptic ulceration or gastrointestinal bleeding
severe liver problems
Clinically proven coronary artery disease, peripheral arterial disease and / or cerebrovascular disease

application

Parecoxib can be administered im or iv .

Web links

Public Assessment Report (EPAR) of the European Medicines Agency (EMA) for: Parecoxib

Individual evidence

↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of N - {[4- (5-methyl-3-phenyl-1,2-oxazol-4-yl) phenyl] sulfonyl} propanamide in the Classification and Labeling Inventory of the European Chemicals Agency is shown, which is derived from a self-classification by the distributor ( ECHA), accessed on July 04, 2020.
↑ Entry on parecoxib. In: Römpp Online . Georg Thieme Verlag, accessed on July 21, 2019.
↑ Mutschler, Geisslinger, Kroemer, Ruth, Schäfer-Korting, Mutschler drug effects, 9th edition, 2008, ISBN 3-8047-1952-X .
↑ ^a ^b Technical information on Dynastat.
↑ ^a ^b ^c ^d ABDA database (as of August 16, 2008) of DIMDI.
↑ ^a ^b ^c Information page of the manufacturer about Dynastat .
↑ Nussmeier NA, Whelton AA, Brown MT, et al. : Complications of the COX-2 inhibitors parecoxib and valdecoxib after cardiac surgery . In: N. Engl. J. Med. . 352, No. 11, March 2005, pp. 1081-91. doi : 10.1056 / NEJMoa050330 . PMID 15713945 .

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of N - {[4- (5-methyl-3-phenyl-1,2-oxazol-4-yl) phenyl] sulfonyl} propanamide in the Classification and Labeling Inventory of the European Chemicals Agency is shown, which is derived from a self-classification by the distributor ( ECHA), accessed on July 04, 2020.

[römpp-2] Entry on parecoxib. In: Römpp Online . Georg Thieme Verlag, accessed on July 21, 2019.

[MAW9-3] Mutschler, Geisslinger, Kroemer, Ruth, Schäfer-Korting, Mutschler drug effects, 9th edition, 2008, ISBN 3-8047-1952-X .

[FI-4] Technical information on Dynastat.

[DIMDI-5] ABDA database (as of August 16, 2008) of DIMDI.

[ST-6] Information page of the manufacturer about Dynastat .

[pmid15713945-7] Nussmeier NA, Whelton AA, Brown MT, et al. : Complications of the COX-2 inhibitors parecoxib and valdecoxib after cardiac surgery . In: N. Engl. J. Med. . 352, No. 11, March 2005, pp. 1081-91. doi : 10.1056 / NEJMoa050330 . PMID 15713945 .