U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H13N3O4S
Molecular Weight 331.346
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIROXICAM

SMILES

CN1C(C(=O)NC2=CC=CC=N2)=C(O)C3=CC=CC=C3S1(=O)=O

InChI

InChIKey=QYSPLQLAKJAUJT-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C15H13N3O4S
Molecular Weight 331.346
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.pfizermedicalinformation.com/en-us/feldene

Piroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). 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. 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. 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. Piroxicam is used for treatment of osteoarthritis and rheumatoid arthritis.

CNS Activity

Originator

Pfizer
420
Curator's Comment: originally brought to market by Pfizer under the tradename Feldene in 1980 # Pfizer

Approval Year

1982
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Catalase
6
Target ID: P04040
Gene ID: 847.0
Gene Symbol: CAT
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 0.414 mM [IC50]
Inhibitor
8504
 4.4 µM [IC50]
Inhibitor
8504
 70.0 µM [IC50]
Inhibitor
8504
 73.8 µM [IC50]
Inhibitor
8504
 7.0 µM [IC50]
Inhibitor
8504
 1.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
FELDENE

Approved Use

FELDENE is a nonsteroidal anti-inflammatory drug indicated for Relief of the signs and symptoms of osteoarthritis (OA) Relief of the signs and symptoms of rheumatoid arthritis (RA)

Launch Date

1982
Primary
Approved
8583
FELDENE

Approved Use

FELDENE is a nonsteroidal anti-inflammatory drug indicated for Relief of the signs and symptoms of osteoarthritis (OA) Relief of the signs and symptoms of rheumatoid arthritis (RA)

Launch Date

1982
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.3 μg/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/27129120
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIROXICAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
135.8 μg × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/27129120
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIROXICAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
40.5 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/27129120
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIROXICAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
40 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
unhealthy, 19 -74
Health Status: unhealthy
Age Group: 19 -74
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Disc. AE: Chest pain, Rash...
AEs leading to
discontinuation/dose reduction:
Chest pain (0.74%)
Rash (0.74%)
Vomiting (0.74%)
Exanthema (0.74%)
Injection site pain (0.74%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
unhealthy, 54
Health Status: unhealthy
Age Group: 54
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
Disc. AE: Nausea, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Nausea
Abdominal pain
Gastric ulcer
Duodenal ulcer
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
unhealthy, 59.7+/-7.4
Health Status: unhealthy
Age Group: 59.7+/-7.4
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Disc. AE: Gastrointestinal disorders, Haemorrhage of digestive tract...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorders (2.6%)
Haemorrhage of digestive tract (0.85%)
Headache (0.85%)
Oedema (0.85%)
Pruritus (0.85%)
Erythema facial (0.85%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
unhealthy, >40
Health Status: unhealthy
Age Group: >40
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
Disc. AE: Epigastric discomfort, Diarrhoea...
AEs leading to
discontinuation/dose reduction:
Epigastric discomfort (2.5%)
Diarrhoea (2.5%)
Loose stools (2.5%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Disc. AE: Cardiac thrombosis, Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Cardiac thrombosis (grade 3-5)
Myocardial infarction (grade 3-5)
Stroke (grade 3-5)
Gastrointestinal disorder NOS (serious)
Bleeding (serious)
Ulceration (serious)
Perforation stomach (grade 3-5)
Perforation of intestine (grade 3-5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Chest pain 0.74%
Disc. AE
40 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
unhealthy, 19 -74
Health Status: unhealthy
Age Group: 19 -74
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Exanthema 0.74%
Disc. AE
40 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
unhealthy, 19 -74
Health Status: unhealthy
Age Group: 19 -74
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Injection site pain 0.74%
Disc. AE
40 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
unhealthy, 19 -74
Health Status: unhealthy
Age Group: 19 -74
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Rash 0.74%
Disc. AE
40 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
unhealthy, 19 -74
Health Status: unhealthy
Age Group: 19 -74
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Vomiting 0.74%
Disc. AE
40 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 40 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
unhealthy, 19 -74
Health Status: unhealthy
Age Group: 19 -74
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Abdominal pain Disc. AE
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
unhealthy, 54
Health Status: unhealthy
Age Group: 54
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
Duodenal ulcer Disc. AE
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
unhealthy, 54
Health Status: unhealthy
Age Group: 54
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
Gastric ulcer Disc. AE
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
unhealthy, 54
Health Status: unhealthy
Age Group: 54
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
Nausea Disc. AE
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
unhealthy, 54
Health Status: unhealthy
Age Group: 54
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6496192
Erythema facial 0.85%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
unhealthy, 59.7+/-7.4
Health Status: unhealthy
Age Group: 59.7+/-7.4
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Haemorrhage of digestive tract 0.85%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
unhealthy, 59.7+/-7.4
Health Status: unhealthy
Age Group: 59.7+/-7.4
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Headache 0.85%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
unhealthy, 59.7+/-7.4
Health Status: unhealthy
Age Group: 59.7+/-7.4
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Oedema 0.85%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
unhealthy, 59.7+/-7.4
Health Status: unhealthy
Age Group: 59.7+/-7.4
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Pruritus 0.85%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
unhealthy, 59.7+/-7.4
Health Status: unhealthy
Age Group: 59.7+/-7.4
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Gastrointestinal disorders 2.6%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
unhealthy, 59.7+/-7.4
Health Status: unhealthy
Age Group: 59.7+/-7.4
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Diarrhoea 2.5%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
unhealthy, >40
Health Status: unhealthy
Age Group: >40
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
Epigastric discomfort 2.5%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
unhealthy, >40
Health Status: unhealthy
Age Group: >40
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
Loose stools 2.5%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
unhealthy, >40
Health Status: unhealthy
Age Group: >40
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
Cardiac thrombosis grade 3-5
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Myocardial infarction grade 3-5
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Perforation of intestine grade 3-5
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Perforation stomach grade 3-5
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Stroke grade 3-5
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Bleeding serious
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Gastrointestinal disorder NOS serious
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Ulceration serious
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
substrate
1193

inhibitor
2438
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
725

OAT2
153

OAT3
747

OAT4
150

Nav1.5
116
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT1
730
 yes [Ki 20.5 uM]
CYP2C9
2497
 yes [Ki 23 uM]
OAT3
749
 yes [Ki 4.88 uM]
OAT2
155
 yes [Ki 70.3 uM]
OAT4
150
 yes [Ki 84.9 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1193
 major
yes (pharmacogenomic study)
Comment: Higher systemic exposure of piroxicam has been noted in subjects with CYP2C9 polymorphisms compared to normal metabolizer type subject
CYP3A4
1946
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Nav1.5
119
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:8249
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8249
ChemicalBook
CB1375282
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1375282
eMolecules
593185
https://www.emolecules.com/cgi-bin/more?vid=593185
MolPort
MolPort-001-888-120
https://www.molport.com/shop/molecule-link/MolPort-001-888-120
Selleck Chemicals
Piroxicam(Feldene)
http://www.selleckchem.com/products/Piroxicam(Feldene).html
ZINC
ZINC000051133897
http://zinc15.docking.org/substances/ZINC000051133897
PubMed

PubMed

TitleDatePubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015-05-18
Lung fibrosis induced by crystalline silica particles is uncoupled from lung inflammation in NMRI mice.
2011-06-10
Apoptosis induced by piroxicam plus cisplatin combined treatment is triggered by p21 in mesothelioma.
2011
The effect of non-steroidal anti-inflammatory agents on behavioural changes and cytokine production following systemic inflammation: Implications for a role of COX-1.
2010-03
Effects of cyclooxygenase inhibitor treatment on the renal toxicity of cisplatin in rats.
2010-02
Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS).
2009-06
The conversion of rapid TCCD nongenomic signals to persistent inflammatory effects via select protein kinases in MCF10A cells.
2009-04
Antirheumatic drug response signatures in human chondrocytes: potential molecular targets to stimulate cartilage regeneration.
2009
Piroxicam: restriction of indications: labelling change. Only half-measures.
2008-10
Effect of acetaminophen, a cyclooxygenase inhibitor, on Morris water maze task performance in mice.
2007-09
Genetic susceptibility to nonsteroidal anti-inflammatory drug-related gastroduodenal bleeding: role of cytochrome P450 2C9 polymorphisms.
2007-08
Immunomodulatory effect of nonsteroidal anti-inflammatory drugs (NSAIDs) at the clinically available doses.
2007-01
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007-01
Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents.
2006-10
Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems.
2006-08
Direct binding of Cu(II)-complexes of oxicam NSAIDs with DNA backbone.
2006-08
Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes.
2005-11
Mechanisms of protection by pantoprazole against NSAID-induced gastric mucosal damage.
2005-07
Identification of HIV-1 integrase inhibitors based on a four-point pharmacophore.
1998-11
Nonsteroidal anti-inflammatory drugs enhance glutathione S-transferase theta levels in rat colon.
1998-08-24
[Cholestatic hepatitis associated with piroxicam use. Case report].
1998-05
Piroxicam and acarbose as chemopreventive agents for spontaneous intestinal adenomas in APC gene 1309 knockout mice.
1998-04
Differential effects of nonsteroidal anti-inflammatory drugs on constitutive and inducible prostaglandin G/H synthase in cultured bone cells.
1997-08
Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity.
1997-03-14
Tenidap inhibits replication of the human immunodeficiency virus-1 in cultured cells.
1997-01-01
Tenidap in rheumatoid arthritis. A 24-week double-blind comparison with hydroxychloroquine-plus-piroxicam, and piroxicam alone.
1995-10
Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition.
1995-09-29
Anti-inflammatory effects of etodolac: comparison with other non-steroidal anti-inflammatory drugs.
1994-12
Fetal renal maldevelopment with oligohydramnios following maternal use of piroxicam.
1994-10
Comparison of ketorolac tromethamine with other injectable nonsteroidal anti-inflammatory drugs for pain-on-injection and muscle damage in the rat.
1994-02
Renal disease and use of topical non-steroidal anti-inflammatory drugs.
1994-01-08
Mechanism of anti-inflammatory action of fepradinol.
1994-01
Nonsteroidal antiinflammatory drugs and certain rare, serious adverse events: a cohort study.
1993-05-01
[Iatrogenic axonal neuropathy and erythroderma induced by piroxicam. Manifestations of hypersensitivity?].
1993
Severe cholestatic jaundice associated with piroxicam.
1991-12
Zidovudine-induced macular edema.
1991-02-15
Aplastic anaemia associated with piroxicam.
1991-02
Piroxicam-induced renal failure following relief of chronic retention.
1989-04
[Acute hemolytic anemia and hepatonephritis caused by piroxicam].
1988-10-01
[Fatal autoimmune hemolytic anemia probably induced by treatment with piroxicam].
1988-03-07
[Hepatonephritis caused by piroxicam].
1987-10
Piroxicam in acute musculoskeletal disorders and sport injuries.
1987
Non-steroidal anti-inflammatory drugs: assessment of risks.
1987
A double-blind multicentre trial of piroxicam and naproxen in osteoarthritis.
1986-01
An interaction between lithium carbonate and piroxicam presenting as lithium toxicity.
1985-08
Piroxicam-induced acute renal failure (anuria)
1985-05
Piroxicam-induced acute interstitial nephritis and minimal-change nephrotic syndrome.
1985
Piroxicam-induced renal disease.
1984-01
Piroxicam-induced renal failure.
1983-11
Piroxicam-induced renal failure and hyperkalemia.
1983-07
Patents

Patents

JP2000327588A
6
JP2000501709A
76
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Sample Use Guides

In Vivo Use Guide
Recommended dose: 20 mg orally once a day
Route of Administration: Oral
In Vitro Use Guide
Contractions induced by bradykinin in guinea-pig gallbladder smooth muscle strips were significantly attenuated by the cyclooxygenase inhibitor piroxicam (10 muM).
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:10:11 GMT 2025
Edited
by admin
on Mon Mar 31 18:10:11 GMT 2025
Record UNII
13T4O6VMAM
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
FELDENE
Preferred Name English
PIROXICAM
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
4-HYDROXY-2-METHYL-N-2-PYRIDINYL-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE 1,1-DIOXIDE
Systematic Name English
piroxicam [INN]
Common Name English
PIROXICAM [MI]
Common Name English
PIROXICAM [EP MONOGRAPH]
Common Name English
NSC-666076
Code English
PIROXICAM [JAN]
Common Name English
PIROXICAM [USP-RS]
Common Name English
2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE, 4-HYDROXY-2-METHYL-N-2-PYRIDINYL-, 1,1-DIOXIDE
Systematic Name English
CP-16171
Code English
PIROXICAM [VANDF]
Common Name English
PIROXICAM ANHYDROUS
Common Name English
CP-16,171
Code English
PIROXICAM [USP MONOGRAPH]
Common Name English
PIROXICAM [USAN]
Common Name English
PIROXICAM [MART.]
Common Name English
PIROXICAM [ORANGE BOOK]
Common Name English
Piroxicam [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QM01AC01
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
WHO-VATC QS01BC06
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
NDF-RT N0000175722
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
WHO-ATC S01BC06
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
NCI_THESAURUS C1915
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
NCI_THESAURUS C1323
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
WHO-ATC M01AC01
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
WHO-ATC M02AA07
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
NDF-RT N0000000160
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
NDF-RT N0000175721
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
WHO-VATC QM02AA07
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
LIVERTOX NBK548425
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
Code System Code Type Description
DRUG CENTRAL
2210
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
DRUG BANK
DB00554
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
CHEBI
8249
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
FDA UNII
13T4O6VMAM
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
RXCUI
8356
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
MERCK INDEX
m8889
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID5021170
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
RS_ITEM_NUM
1544508
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
CAS
36322-90-4
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
IUPHAR
7273
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
ECHA (EC/EINECS)
252-974-3
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
NSC
666076
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
PUBCHEM
54676228
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
RXCUI
68115
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
ALTERNATIVE
SMS_ID
100000092492
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
EVMPD
SUB127114
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
LACTMED
Piroxicam
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
EVMPD
SUB09936MIG
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
WIKIPEDIA
PIROXICAM
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
INN
3713
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL527
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
NCI_THESAURUS
C751
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
MESH
D010894
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
DAILYMED
13T4O6VMAM
Created by admin on Mon Mar 31 18:10:11 GMT 2025 , Edited by admin on Mon Mar 31 18:10:11 GMT 2025
PRIMARY
Related Record Type Details
OAT-1
TRANSPORTER -> INHIBITOR
Structure of PIROXICAM
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
OAT-2
TRANSPORTER -> INHIBITOR
Structure of PIROXICAM OLAMINE
SALT/SOLVATE -> PARENT
Structure of PIROXICAM
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
PIROXICAM BETADEX
SUB_CONCEPT->SUBSTANCE
Structure of PIROXICAM MONOHYDRATE
SOLVATE->ANHYDROUS
Structure of PIROXICAM MONOHYDRATE
SALT/SOLVATE -> PARENT
OAT-4
TRANSPORTER -> INHIBITOR
OAT-3
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of 2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC ACID, 4-HYDROXY-2-METHYL-, 1,1-DIOXIDE
METABOLITE -> PARENT
Structure of 6H,7H-PYRIDO(2',1':2,3)PYRIMIDO(5,4-C)(1,2)BENZOTHIAZIN-7-ONE, 6-METHYL-, 5,5-DIOXIDE
METABOLITE -> PARENT
Structure of 5'-HYDROXYPIROXICAM
METABOLITE -> PARENT
Structure of 6H,7H-PYRIDO(2',1':2,3)PYRIMIDO(5,4-C)(1,2)BENZOTHIAZIN-7-ONE, 6-METHYL-, 5,5-DIOXIDE
PARENT -> METABOLITE
Related Record Type Details
Structure of SACCHARIN N-(2-ACETIC ACID METHYL ESTER)
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1-METHYLETHYL 4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLATE 1,1-DIOXIDE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of DESMETHYL PIROXICAM
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of METHYL 4-HYDROXY-2-METHYL-2H-1,2-BENZOTHIAZINE-3-CARBOXYLATE 1,1-DIOXIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of SACCHARIN N-(2-ACETIC ACID ETHYL ESTER)
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of DESPYRIDYL PIROXICAM
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 2-Aminopyridine
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-HYDROXY-2-METHYL-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC ACID ETHYLESTER 1,1-DIOXIDE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of SACCHARIN N-(2-ACETIC ACID ISOPROPYL ESTER)
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of ISOPROPYL-4-HYDROXY-2-METHYL-2H-1,2-BENZOTHIAZINE-3-CARBOXYLATE-1,1-DIOXIDE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of ETHYL 4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLATE 1,1-DIOXIDE
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
Structure of PIROXICAM
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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