Piroxicam

Piroxicam

Clinical data
Trade names	Feldene and many others
AHFS/Drugs.com	Monograph
MedlinePlus	a684045
Pregnancy category	AU: C US: C (Risk not ruled out) D (US), if used during the 3rd trimester, as it may cause ductus arteriosus.
Routes of administration	Oral
ATC code	M01AC01 (WHO) M02AA07 (WHO), S01BC06 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Protein binding	99%
Metabolism	Liver-mediated hydroxylation and glucuronidation
Biological half-life	50 hours
Excretion	Urine, faeces
Identifiers
IUPAC name 4-Hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
CAS Number	36322-90-4 Y
PubChem CID	5280452
IUPHAR/BPS	7273
DrugBank	DB00554 Y
ChemSpider	10442653 Y
UNII	13T4O6VMAM
KEGG	D00127 Y
ChEBI	CHEBI:8249 Y
ChEMBL	CHEMBL527 Y
ECHA InfoCard	100.048.144
Chemical and physical data
Formula	C15H13N3O4S
Molar mass	331.348 g/mol
3D model (Jmol)	Interactive image
SMILES OC=2c1ccccc1S(=O)(=O)N(C)C=2C(=O)Nc3ccccn3
InChI InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20) Y Key:QYSPLQLAKJAUJT-UHFFFAOYSA-N Y

Piroxicam /paɪˈrɒksɪˌkæm/ (INN, BAN, USAN, AAN; in some countries it is spelt piroksikam or piroxikam) is a non-steroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve the symptoms of painful, inflammatory conditions like arthritis. Piroxicam works by preventing the production of a certain type of body chemical called prostaglandins which are involved in the mediation of pain, stiffness, tenderness and swelling. The medicine is available as capsules, tablets and (not in all countries) as a prescription-free gel 0.5%. It is also available in a betadex formulation, which allows a more rapid absorption of piroxicam from the digestive tract.

It was originally brought to market by Pfizer under the tradename Feldene in 1980, became generic in 1992, and is marketed worldwide under many brandnames.

It used in the treatment of rheumatoid and osteoarthritis, primary dysmenorrhoea, postoperative pain; and act as an analgesic, especially where there is an inflammatory component. The European Medicines Agency issued a review of its use in 2007 and recommended that its use be limited to the treatment of chronic inflammatory conditions, as it only in these circumstances that its risk-benefit ratio proves to be favourable.