Piroxicam

Structural formula
General
Non-proprietary name	Piroxicam
other names	4-Hydroxy-2-methyl- N -pyridin-2-yl-2 H -1,2-benzothiazine-3-carboxamide-1,1-dioxide ( IUPAC ); Piroxicamum ( Latin );
Molecular formula	C 15 H 13 N 3 O 4 S
External identifiers / databases
EC number	252-974-3
ECHA InfoCard	100.048.144
PubChem	54676228
DrugBank	DB00554
Wikidata	Q408676
Drug information
ATC code	M01 AC01 ; M02 AA07 ; S01 BC06 ;
Drug class	non-steroidal anti-inflammatory drug
Mechanism of action	Cyclooxygenase inhibitors
properties
Molar mass	331.35 g mol −1
Melting point	203 ° C ( polymorph I ) ; approx. 198 ° C ( Polymorph II ); 202 ° C ( polymorph III );
pK s value	6.3
solubility	in water at 25 ° C: 14.3 mg l −1 ( polymorph I ); 16.7 mg l −1 ( polymorph II ); 17.0 mg l −1 ( polymorph III ); 16.5 mg l −1 ( monohydrate );
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	216 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 .

Piroxicam is a drug , more precisely a nonsteroidal anti-inflammatory drug (NSAID, NSAID) from the group of oxicams with a long half-life (approx. 50 hours in humans). It was formerly in pain of the musculoskeletal system used ( arthritis , rheumatism ), but due to the risk-benefit assessment for this application, with the exception of ankylosing spondylitis , now contraindicated where it is second-line.

Piroxicam cinnamate is also called cinnoxicam .

history

The Pfizer company (USA) started a research project on nonsteroidal anti-inflammatory drugs (NSAIDs) in 1967 . In this context, JG Lombardino and EH Wiseman succeeded in synthesizing piroxicam for the first time in 1972. It was brought onto the market in 1980 under the trade name Felden and has also been available as a generic since 1992 .

pharmacology

Mechanism of action

Like almost all NSAIDs, piroxicam reversibly inhibits the enzyme cyclooxygenase (COX). In addition, piroxicam inhibits the immigration of monocytes and polymorphonuclear leukocytes , the release of oxygen radicals from activated leukocytes and of cartilage-destroying lysosomal enzymes. Based on in vitro studies, the cartilage metabolism remains unaffected. It works by analgesic ( analgesic ), anti-inflammatory ( antiphlogistic ) and antipyretic ( antipyretic ).

In domestic dogs , piroxicam also has an anti- tumor effect on certain tumors ( urothelial carcinoma of the urinary bladder, squamous cell carcinoma of the oral cavity, tubulopapillary polyps of the rectum). The exact mechanism of action is so far unknown, it is probably based on a reduction in the immunosuppressive effect of prostaglandin E2 .

Side effects and contraindications

The following side effects can occur: skin rash , stomach and duodenal ulcers , edema , hepatitis , cholestasis , colitis , nephritis , malaise, phototoxia , Henoch-Schönlein purpura , hair loss and increased blood pressure . With long-term use, monitoring of kidney and liver values is necessary.

Piroxicam is contraindicated for blood formation disorders and gastrointestinal ulcers . The product should not be used during breastfeeding and pregnancy.

In July 2007, the European Medicines Agency recommended restricting the use of piroxicam as it has more gastrointestinal and skin side effects than other NSAIDs.

Trade names

Monopreparations: Brexidol (D), Felden (D, A, CH), Piroflam (D), Pirobeta (D), Pirosol (CH), numerous generics (D, A, CH) Anmatic (Thailand)

Web links

Vetpharm entry on Piroxicam , accessed November 21, 2011.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g F. Lai, E. Pini, G. Angioni, ML Manca, J. Perricci, C. Sinico, AM Fadda: Nanocrystals as tool to improve piroxicam dissolution rate in novel orally disintegrating tablets in Eur J Pharm Biopharm 79 (2011) 552-558, doi : 10.1016 / j.ejpb.2011.07.005 .
↑ ^a ^b Entry on piroxicam in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Data sheet Piroxicam from Sigma-Aldrich , accessed on April 21, 2011 ( PDF ).
↑ https://www.akdae.de/Arzneimittelsicherheit/RHB/Archiv/2007/40-20071011.pdf
↑ External identifiers or database links for piroxicam cinnamate : CAS number: 87234-24-0, EC number: 643-086-0, ECHA InfoCard: 100.171.137 , PubChem : 6436090 , ChemSpider : 4940766 , Wikidata : Q27268143 .
↑ Discovery of piroxicam. Retrieved March 20, 2017 .
^ Wolf-Dieter Müller-Jahncke , Christoph Friedrich , Ulrich Meyer: Medicinal history . 2nd, revised and expanded edition. Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 2005, ISBN 3-8047-2113-3 , p. 140 .
↑ rheumatism online: EMEA significantly restricts the approval of piroxicam .
↑ EMEA: Questions and Answers on the review of Piroxicam (PDF; 56 kB), June 21, 2007.

[Lai-1] ↑ ^a ^b ^c ^d ^e ^f ^g F. Lai, E. Pini, G. Angioni, ML Manca, J. Perricci, C. Sinico, AM Fadda: Nanocrystals as tool to improve piroxicam dissolution rate in novel orally disintegrating tablets in Eur J Pharm Biopharm 79 (2011) 552-558, doi : 10.1016 / j.ejpb.2011.07.005 .

[ChemIDplus-2] Entry on piroxicam in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-3] Data sheet Piroxicam from Sigma-Aldrich , accessed on April 21, 2011 ( PDF ).

[4] ttps://www.akdae.de/Arzneimittelsicherheit/RHB/Archiv/2007/40-20071011.pdf

[5] External identifiers or database links for piroxicam cinnamate : CAS number: 87234-24-0, EC number: 643-086-0, ECHA InfoCard: 100.171.137 , PubChem : 6436090 , ChemSpider : 4940766 , Wikidata : Q27268143 .

[6] Discovery of piroxicam. Retrieved March 20, 2017 .

[7] Wolf-Dieter Müller-Jahncke , Christoph Friedrich , Ulrich Meyer: Medicinal history . 2nd, revised and expanded edition. Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 2005, ISBN 3-8047-2113-3 , p. 140 .

[8] rheumatism online: EMEA significantly restricts the approval of piroxicam .

[9] EMEA: Questions and Answers on the review of Piroxicam (PDF; 56 kB), June 21, 2007.