Piroxicam

Piroxicam

Systematic (IUPAC) name
4-Hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
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.
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Routes of administration	Oral
Pharmacokinetic data
Protein binding	99%
Metabolism	Liver-mediated hydroxylation and glucuronidation
Biological half-life	50 hours
Excretion	Urine, faeces
Identifiers
CAS Number	36322-90-4 Y
ATC code	M01AC01 (WHO) M02AA07, S01BC06
PubChem	CID: 5280452
IUPHAR/BPS	7273
DrugBank	DB00554 Y
ChemSpider	10442653 Y
UNII	13T4O6VMAM Y
KEGG	D00127 Y
ChEBI	CHEBI:8249 Y
ChEMBL	CHEMBL527 Y
Chemical data
Formula	C15H13N3O4S
Molecular mass	331.348 g/mol
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
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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.

Medical uses

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.

Adverse effects

Main article: Non-steroidal anti-inflammatory drug

As with other NSAIDs the principal side effects include: digestive complaints like nausea, discomfort, diarrhoea and bleeds or ulceration of the stomach, as well as headache, dizziness, nervousness, depression, drowsiness, insomnia, vertigo, hearing disturbances (such as tinnitus), high blood pressure, oedema, light sensitivity, skin reactions (including, albeit rarely, Stevens-Johnson syndrome and toxic epidermal necrolysis) and rarely, kidney failure, pancreatitis, liver damage, visual disturbances, pulmonary eosinophilia and alveolitis. Compared to other NSAIDs it is more prone to causing GI disturbances and serious skin reactions.

Mechanism of action

Main article: Non-steroidal anti-inflammatory drug

Piroxicam is an NSAID and, as such, is a non-selective COX inhibitor possessing both analgesic and antipyretic properties.

Chemical properties

Piroxicam exists as enol tautomer in organic solvents and as zwitterionic form in water.

History

The project that produced piroxicam began in 1962 at Pfizer; the first clinical trial results were reported in 1977, and the product launched in 1980 under the brand name "Feldene". Major patents expired in 1992 and the drug is marketed worldwide under many brandnames.

See also

• Meloxicam