Structure via PubChem · Public domain (PubChem)
piroxicam
Sign in to saveAlso known as CP-16171, pyroxycam, 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid
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 parent
Chemical data
- Formula
- C15H13N3O4S
- Molecular weight
- 331.3 g/mol
- IUPAC name
- 4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-yl-1lambda6,2-benzothiazine-3-carboxamide
- SMILES
- CN1C(=C(C2=CC=CC=C2S1(=O)=O)O)C(=O)NC3=CC=CC=N3
- InChIKey
- QYSPLQLAKJAUJT-UHFFFAOYSA-N
- XLogP
- 3.1
- Polar surface area
- 108 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
4,366 papers- Piroxicam: Source for Synthesis of Central Nervous System (CNS) Acting Drugs.Central nervous system agents in medicinal chemistry · 2017
- Piroxicam: what's new?European journal of rheumatology and inflammation · 1981
- Effect of piroxicam administration in infertile women undergoing assisted reproductive technologies: A systematic review and meta-analysis.Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology · 2021
- Piroxicam-β-cyclodextrin: a GI safer piroxicam.Current medicinal chemistry · 2013
- In vivo Piroxicam Metabolites: Possible Source for Synthesis of Central Nervous System (CNS) Acting Depressants.Central nervous system agents in medicinal chemistry · 2017
via PubMed
Wikidata facts
- Subclass of
- non-steroidal anti-inflammatory drug
- Has part
- carbon
- Mass
- 331.062677
- Has use
- medication
Show 12 more facts
- significant drug interaction
- tacrolimus
- Commons category
- Piroxicam
- defined daily dose
- 20
- chemical formula
- C₁₅H₁₃N₃O₄S
- medical condition treated
- osteoarthritis
- isomeric SMILES
- CN1C(=C(C2=CC=CC=C2S1(=O)=O)O)/C(=N/C3=CC=CC=N3)/O
- canonical SMILES
- CN1C(=C(C2=CC=CC=C2S1(=O)=O)O)C(=O)NC3=CC=CC=N3
- World Health Organisation international non-proprietary name
- piroxicam
- subject has role
- non-steroidal anti-inflammatory drug
- MCN code
- 2935.90.23
- physically interacts with
- Prostaglandin-endoperoxide synthase 2
- legal status (medicine)
- boxed warning
Sources (7)
via Wikidata · CC0
~3 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- Adverse effects
- Mechanism of action
- Chemical properties
- History
- See also
- References
- Further reading
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.
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.
Excerpted from Wikipedia’s “piroxicam” article, available under the CC BY-SA 4.0 licence.