Carprofen

Structural formula
	1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Carprofen
other names	( RS ) -2- (6-chloro-9 H -carbazol-2-yl) propanoic acid; (±) -2- (6-Chloro-9 H -carbazol-2-yl) propanoic acid; DL -2- (6-chloro-9 H -carbazol-2-yl) propanoic acid;
Molecular formula	C 15 H 12 ClNO 2
External identifiers / databases
EC number	258-712-4
ECHA InfoCard	100.053.357
PubChem	2581
ChemSpider	2483
DrugBank	DB00821
Wikidata	Q905755
Drug information
ATC code	Q M01AE91
Drug class	Anti-inflammatory
properties
Molar mass	273.71 g · mol -1
Physical state	firmly
Melting point	197-198 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301
	P: 301 + 310
Toxicological data	74 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carprofen is a nonsteroidal anti-inflammatory drug from the group of aryl propionic acid derivatives that is frequently used in veterinary medicine . The active ingredient is not approved in human medicine .

effect

Carprofen is one of the so-called non-steroidal anti-inflammatory drugs (NSAIDs) and has a strong analgesic , antipyretic and anti-inflammatory effect. As with all NSAIDs, the mechanism of action is based on the inhibition of cyclooxygenases (COX), which catalyzes the formation of prostaglandins , prostacyclin and thromboxane from arachidonic acid. The specificity for cyclooxygenase-2 (COX-2) is very variable depending on the species, from weak in dogs to pronounced in horses and cats . However, the formation of thromboxane and prostaglandin E is only slightly influenced. The main effect of carprofen is probably based on the inhibition of the enzyme phospholipase A₂ , which releases arachidonic acid from phospholipids in the cells , which means that less substrate is available for prostaglandin synthesis.

In dogs, a marked, dose-dependent stimulation of the formation of glycosaminoglycans by cartilage cells has been demonstrated. In high doses, however, the synthesis of these basic building blocks of cartilage is inhibited.

Carprofen also affects the immune responses and inhibits the formation of IgM - rheumatoid factor .

Carprofen can be administered both parenterally and orally and is rapidly absorbed . In the body, it is 99% bound to proteins . The metabolism occurs in the liver , excretion in most animals mainly through the bile , however, to 10-20% in horses predominantly via the kidney . The plasma half-life is 20 to 65 hours. Carprofen can cross the blood brain barrier .

application

Due to its positive effect on the articular cartilage and its pain-relieving properties, carprofen is preferred for joint diseases. In addition, it can be used for all other painful processes and also for pain therapy before and after operations.

Side effects and contraindications

Carprofen is well tolerated even with long-term treatments. Rare side effects include vomiting , diarrhea , anorexia, and lethargy . Especially in cats, the agent has a damaging effect on the intestines, which is why oral use in these animals is not permitted and is not recommended by the manufacturer. In dogs, liver and kidney damage has been observed in rare cases (less than 0.02% of treated animals).

The product should not be used in animals with diseases of the gastric or intestinal mucosa , renal insufficiency , heart failure or blood clotting disorders . The agent has a toxic effect on embryos , which is why it is not recommended to use it during pregnancy .

Trade names

Acticarp, Bonocarp (out of trade), Canidryl, Carprieve, Carprodyl, Carprogesic, Carprosol, Carprotab, Carprox, Dolagis, Dolocarp, Rimadyl, Rimifin, Rycarfa

Individual evidence

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 303, ISBN 978-0-911910-00-1 .
↑ ^a ^b ^c data sheet Carprofen at Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
↑ ^a ^b Entry on Carprofen at Vetpharm, accessed on November 21, 2011.

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 303, ISBN 978-0-911910-00-1 .

[Sigma-2] ta sheet Carprofen at Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).

[vetpharm-3] Entry on Carprofen at Vetpharm, accessed on November 21, 2011.