Drug/Small Molecule:
piroxicam

2D structure

Overview

Generic Names: AK1015; piroxicam
IUPAC Name: (3E)-3-[hydroxy-(pyridin-2-ylamino)methylidene]-2-methyl-1,1-dioxobenzo[e]thiazin-4-one
Trade Names: Akten; Apo-Piroxicam; Artroxicam; Baxo; Bruxicam; Caliment; Erazon; Feldene; Flogobene; Geldene; Improntal; Larapam; Pipoxicam; Pirkam; Piroflex; Reudene; Riacen; Roxicam; Roxiden; Sasulen; Solocalm; Zunden; piroxicam usp
PharmGKB Accession Id: PA450985

Description

A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily. [PubChem]

Indication

For treatment of osteoarthritis and rheumatoid arthritis.

ATC Therapeutic Categories

  • M01AC:Oxicams
  • M02AA:Antiinflammatory preparations, non-steroids for topical use
  • S01BC:Antiinflammatory agents, non-steroids

Pharmacology and Interactions

Mechanism Of Action

The antiinflammatory effect of Piroxicam may result from the reversible inhibition of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. The prostaglandins are produced by an enzyme called Cox-1. Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets.

Pharmacology

Piroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). Piroxicam works by reducing hormones that cause inflammation and pain in the body. Piroxicam is used to reduce the pain, inflammation, and stiffness caused by rheumatoid arthritis and osteoarthritis.

Food Interactions

Take with food. Avoid alcohol.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Renal

Absorption

Well absorbed following oral administration.

Half Life

30 to 86 hours

Toxicity

Symptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.

Chemical Properties

Chemical Formula:

C15H13N3O4S

SMILES Code:

CN1C(=C(c2ccccc2S1(=O)=O)O)C(=O)Nc3ccccn3

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

331.346 / 331.0627

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
AKR1C3
  •   
  • PD
  • PK
  •   
  •   
Pathways
Phenotype data available No genotype data Literature annotations available Not annotated
AKT1
  •   
  • PD
  • PK
  •   
  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
BCAR1
  •   
  • PD
  • PK
  •   
  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
CASP3
  •   
  • PD
  • PK
  •   
  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
CASP9
  •   
  • PD
  • PK
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  •   
Pathways
Phenotype data available No genotype data Literature annotations available Not annotated
CDKN1A
  •   
  • PD
  • PK
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  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Not annotated
CDKN1B
  •   
  • PD
  • PK
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  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
CTNNB1
  •   
  • PD
  • PK
  •   
  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2C9
  • CO
  • PD
  • PK
  •   
  • GN
Publications, Pathways
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2D6
  •   
  • PD
  • PK
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  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
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  • PD
  • PK
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  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
DDIT3
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  • PD
  • PK
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  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
IGFBP3
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  • PD
  • PK
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  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
MMP9
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  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
PDK1
  •   
  • PD
  • PK
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  •   
Pathways
No phenotype data Genotype Data Available Literature annotations available Not annotated
PLA2G2A
  •   
  • PD
  • PK
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  •   
Pathways
No phenotype data Genotype Data Available Literature annotations available Not annotated
PLA2G4A
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  • PD
  • PK
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  •   
Pathways
No phenotype data Genotype Data Available Literature annotations available Not annotated
PPARG
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  • PD
  • PK
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  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
PTGDS
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  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
PTGES
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  • PD
  • PK
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Pathways
No phenotype data Genotype Data Available Literature annotations available Has annotations
PTGIS
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  • PD
  • PK
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Pathways
Phenotype data available No genotype data Literature annotations available Not annotated
PTGS1
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  • PD
  • PK
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  •   
Pathways
Phenotype data available No genotype data Literature annotations available Not annotated
PTGS2
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  • PD
  • PK
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  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
SLC22A11
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  •   
  •   
  • FA
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Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
SLC22A6
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  •   
  •   
  • FA
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
SLC22A8
  •   
  •   
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
SLC22A9
  •   
  •   
  •   
  • FA
  •   
Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
TBXAS1
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  • PD
  • PK
  •   
  •   
Pathways
Phenotype data available No genotype data Literature annotations available Not annotated
VEGFA
  •   
  • PD
  • PK
  •   
  •   
Pathways

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

PharmGKB Curated Pathways

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

acebutolol Risk of inhibition of renal prostaglandins
acenocoumarol The NSAID increases the anticoagulant effect
alendronate Increased risk of gastric toxicity
anisindione The NSAID increases the anticoagulant effect
atenolol Risk of inhibition of renal prostaglandins
betaxolol Risk of inhibition of renal prostaglandins
bevantolol Risk of inhibition of renal prostaglandins
bisoprolol Risk of inhibition of renal prostaglandins
carteolol Risk of inhibition of renal prostaglandins
carvedilol Risk of inhibition of renal prostaglandins
cyclosporine Monitor for nephrotoxicity
dicumarol The NSAID increases the anticoagulant effect
esmolol Risk of inhibition of renal prostaglandins
labetalol Risk of inhibition of renal prostaglandins
lithium The NSAID increases serum levels of lithium
methotrexate The NSAID increases the effect and toxicity of methotrexate
metoprolol Risk of inhibition of renal prostaglandins
nadolol Risk of inhibition of renal prostaglandins
oxprenolol Risk of inhibition of renal prostaglandins
penbutolol Risk of inhibition of renal prostaglandins
pindolol Risk of inhibition of renal prostaglandins
practolol Risk of inhibition of renal prostaglandins
propranolol Risk of inhibition of renal prostaglandins
ritonavir Ritonavir increases the toxicity of piroxicam
sotalol Risk of inhibition of renal prostaglandins
timolol Risk of inhibition of renal prostaglandins
warfarin The NSAID increases the anticoagulant effect

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data No literature annotations Not annotated
Adenomatous Polyposis Coli
  •   
  • PD
  • PK
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  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
Arthritis, Rheumatoid
  •   
  • PD
  • PK
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  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Not annotated
Asthma
  •   
  • PD
  • PK
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  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Not annotated
Colonic Neoplasms
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  • PD
  • PK
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Pathways
No phenotype data No genotype data No literature annotations Not annotated
Dysmenorrhea
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  • PD
  • PK
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Pathways
No phenotype data No genotype data No literature annotations Not annotated
Fever
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  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
Hemorrhage
  • CO
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  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Inflammation
  •   
  • PD
  • PK
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  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
Osteoarthritis
  •   
  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
Pain
  •   
  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
Spondylitis, Ankylosing
  •   
  • PD
  • PK
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  •   
Pathways

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Curated Phenotype Datasets

These datasets are sorted alphabetically by title.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

Downloads

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LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00554
KEGG Compound ID:
C01608
KEGG Drug ID:
D00127
PubChem Compound ID:
5280452
PubChem Substance ID:
4761

Common Searches

Search PubMed
Search Medline Plus
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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
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