Piroxicam

Overview

Piroxicam is a nonsteroidal 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 endogenous prostaglandins which are involved in the mediation of pain, stiffness, tenderness and swelling. The medicine is available as capsules, tablets and, in some 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. Piroxicam is one of the few NSAIDs that can be given parenteral routes.[1][2][3] WP⚠ Wikipedia itself has flagged this text: citation needed.

It was patented in 1968 by Pfizer and approved for medical use in 1979. It became generic in 1992, and is marketed worldwide under many brand names.[4][5][6] WP

Uses, dosage and effects

Medical uses

It is used in the treatment of certain inflammatory conditions like rheumatoid and osteoarthritis, primary dysmenorrhoea, and postoperative pain; it acts 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 is only in these circumstances that its risk-benefit ratio proves to be favourable.[1][3][7] WP

Risks and side effects

Adverse effects

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 fibrosing alveolitis. Compared to other NSAIDs it is more prone to causing gastrointestinal disturbances and serious skin reactions.[3] WP

In October 2020, the U.S. Food and Drug Administration (FDA) required the prescribing information to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid. They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[8][9] WP

Pharmacology

Mechanism of action

Piroxicam is an NSAID and, as such, is a non-selective COX inhibitor possessing both analgesic and antipyretic properties.[3] WP

History

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.[5][6][10] WP

Chemistry

Formula

C15H13N3O4S PC

CAS number

36322-90-4 PC

Molar mass (g/mol)

331.3 PC

IUPAC name (computed by PubChem)

4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-yl-1lambda6,2-benzothiazine-3-carboxamide PC

SMILES

CN1C(=C(C2=CC=CC=C2S1(=O)=O)O)C(=O)NC3=CC=CC=N3 PC

InChIKey

QYSPLQLAKJAUJT-UHFFFAOYSA-N PC

PubChem CID

54676228

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Piroxicam. 14 January 2014
2. Other TGA Approved Terminology for Medicines, Section 1 – Chemical Substances. July 1999
3. Other Joint Formulary Committee. British National Formulary (BNF). 2013
4. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006
5. Journal / agency Lombardino JG, Lowe JA. The role of the medicinal chemist in drug discovery--then and now. Nature Reviews. Drug Discovery. October 2004. doi:10.1038/nrd1523 · PMID 15459676
6. Other International listings for piroxicam
7. Journal / agency Committee for medicinal products for human use (CHMP) opinion following an Article 31(2) referral for Piroxicam containing medicinal products. 20 September 2007
8. Journal / agency FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications. 15 October 2020
9. Journal / agency NSAIDs may cause rare kidney problems in fetuses. 21 July 2017
10. Journal / agency Weintraub M, Jacox RF, Angevine CD, Atwater EC. Piroxicam (CP 16171) in rheumatoid arthritis: a controlled clinical trial with novel assessment techniques. The Journal of Rheumatology. 1977. PMID 342691

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.