Piroxicam

Piroxicam
Skeletal formula of piroxicam
Space-filling model of the piroxicam molecule
Clinical data
Pronunciation/paɪˈrɒksɪˌkæm/
Trade namesFeldene, others[1]
Other namesPiroksikam, piroxikam
AHFS/Drugs.comMonograph
MedlinePlusa684045
Pregnancy
category
  • AU: C
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding99%[4]
MetabolismLiver-mediated hydroxylation and glucuronidation[4]
Elimination half-life50 hours[4]
ExcretionUrine, faeces
Identifiers
  • 4-Hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.144 Edit this at Wikidata
Chemical and physical data
FormulaC15H13N3O4S
Molar mass331.35 g·mol−1
3D model (JSmol)
  • OC=2c1ccccc1S(=O)(=O)N(C)C=2C(=O)Nc3ccccn3
  • 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) checkY
  • Key:QYSPLQLAKJAUJT-UHFFFAOYSA-N checkY
  (verify)

Piroxicam is a nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve the symptoms of painful inflammatory conditions like arthritis.[4][5] Piroxicam works by preventing the production of endogenous prostaglandins which are involved in the mediation of pain, stiffness, tenderness and swelling.[4] The medicine is available as capsules, tablets and, in some countries, as a prescription-free gel 0.5%.[6] It is also available in a betadex formulation, which allows a more rapid absorption of piroxicam from the digestive tract.[4] Piroxicam is one of the few NSAIDs that can be given parenteral routes.[citation needed]

It was patented in 1968 by Pfizer and approved for medical use in 1979.[7] It became generic in 1992,[8] and is marketed worldwide under many brandnames.[1]

  1. ^ a b Cite error: The named reference drugsInternat was invoked but never defined (see the help page).
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  3. ^ "Active substance: piroxicam" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 10 December 2020.
  4. ^ a b c d e f Brayfield A, ed. (14 January 2014). "Piroxicam". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Archived from the original on 28 August 2021. Retrieved 24 June 2014.
  5. ^ "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (PDF). Therapeutic Goods Administration, Department of Health and Ageing. Australian Government. July 1999. p. 97.
  6. ^ Cite error: The named reference BNF was invoked but never defined (see the help page).
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 519. ISBN 9783527607495.
  8. ^ Cite error: The named reference NRDD was invoked but never defined (see the help page).