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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=C(C=CC=C3)S1(=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
407
Curator's Comment: originally brought to market by Pfizer under the tradename Feldene in 1980 # Pfizer

Approval Year

1982
94
Targets

Targets

Primary TargetPharmacologyConditionPotency
Catalase
6
Target ID: P04040
Gene ID: 847.0
Gene Symbol: CAT
Target Organism: Homo sapiens (Human)
Inhibitor
8228
 0.414 mM [IC50]
Inhibitor
8228
 4.4 µM [IC50]
Target ID: Aminopeptidase activity
Inhibitor
8228
 70.0 µM [IC50]
Inhibitor
8228
 73.8 µM [IC50]
Inhibitor
8228
 7.0 µM [IC50]
Inhibitor
8228
 1.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
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

3.86812805E11
Primary
Approved
8360
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

3.86812805E11
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
Page: p.260
unhealthy, 19 -74
n = 135
Health Status: unhealthy
Condition: Acute sprains|Tendinitis| Low back pain
Age Group: 19 -74
Sex: M+F
Population Size: 135
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Page: p.260
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
Page: p.260
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
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
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
Page: p.158
unhealthy, 59.7+/-7.4
n = 117
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: 59.7+/-7.4
Sex: M+F
Population Size: 117
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Page: p.158
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
Page: p.158
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
Page: p.233
unhealthy, >40
n = 40
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: >40
Sex: M+F
Population Size: 40
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
Page: p.233
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
Page: p.233
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
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
Page: p.1
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
Page: p.260
unhealthy, 19 -74
n = 135
Health Status: unhealthy
Condition: Acute sprains|Tendinitis| Low back pain
Age Group: 19 -74
Sex: M+F
Population Size: 135
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Page: p.260
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
Page: p.260
unhealthy, 19 -74
n = 135
Health Status: unhealthy
Condition: Acute sprains|Tendinitis| Low back pain
Age Group: 19 -74
Sex: M+F
Population Size: 135
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Page: p.260
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
Page: p.260
unhealthy, 19 -74
n = 135
Health Status: unhealthy
Condition: Acute sprains|Tendinitis| Low back pain
Age Group: 19 -74
Sex: M+F
Population Size: 135
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Page: p.260
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
Page: p.260
unhealthy, 19 -74
n = 135
Health Status: unhealthy
Condition: Acute sprains|Tendinitis| Low back pain
Age Group: 19 -74
Sex: M+F
Population Size: 135
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Page: p.260
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
Page: p.260
unhealthy, 19 -74
n = 135
Health Status: unhealthy
Condition: Acute sprains|Tendinitis| Low back pain
Age Group: 19 -74
Sex: M+F
Population Size: 135
Sources:
https://pubmed.ncbi.nlm.nih.gov/2932357
Page: p.260
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
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
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
Page: p.158
unhealthy, 59.7+/-7.4
n = 117
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: 59.7+/-7.4
Sex: M+F
Population Size: 117
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Page: p.158
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
Page: p.158
unhealthy, 59.7+/-7.4
n = 117
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: 59.7+/-7.4
Sex: M+F
Population Size: 117
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Page: p.158
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
Page: p.158
unhealthy, 59.7+/-7.4
n = 117
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: 59.7+/-7.4
Sex: M+F
Population Size: 117
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Page: p.158
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
Page: p.158
unhealthy, 59.7+/-7.4
n = 117
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: 59.7+/-7.4
Sex: M+F
Population Size: 117
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Page: p.158
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
Page: p.158
unhealthy, 59.7+/-7.4
n = 117
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: 59.7+/-7.4
Sex: M+F
Population Size: 117
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Page: p.158
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
Page: p.158
unhealthy, 59.7+/-7.4
n = 117
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: 59.7+/-7.4
Sex: M+F
Population Size: 117
Sources:
https://pubmed.ncbi.nlm.nih.gov/9093797
Page: p.158
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
Page: p.233
unhealthy, >40
n = 40
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: >40
Sex: M+F
Population Size: 40
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
Page: p.233
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
Page: p.233
unhealthy, >40
n = 40
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: >40
Sex: M+F
Population Size: 40
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
Page: p.233
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
Page: p.233
unhealthy, >40
n = 40
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: >40
Sex: M+F
Population Size: 40
Sources:
https://pubmed.ncbi.nlm.nih.gov/2202544
Page: p.233
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
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
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018147s044lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1709
substrate
1010

inhibitor
1752
inhibitor
1599

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
595

OAT2
144

OAT3
636

OAT4
145

Nav1.5
95
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT1
599
 yes [Ki 20.5 uM]
CYP2C9
1803
 yes [Ki 23 uM]
OAT3
638
 yes [Ki 4.88 uM]
OAT2
146
 yes [Ki 70.3 uM]
OAT4
145
 yes [Ki 84.9 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1010
 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
1709
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Nav1.5
98
hERG
1632
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
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
eMolecules
593185
https://www.emolecules.com/cgi-bin/more?vid=593185
PubMed

PubMed

TitleDatePubMed
Piroxicam-induced renal failure and hyperkalemia.
1983 Jul
Piroxicam-induced renal failure.
1983 Nov
Piroxicam-induced renal disease.
1984 Jan
Piroxicam-induced acute interstitial nephritis and minimal-change nephrotic syndrome.
1985
An interaction between lithium carbonate and piroxicam presenting as lithium toxicity.
1985 Aug
Piroxicam-induced acute renal failure (anuria).
1985 May
A double-blind multicentre trial of piroxicam and naproxen in osteoarthritis.
1986 Jan
Piroxicam in acute musculoskeletal disorders and sport injuries.
1987
Non-steroidal anti-inflammatory drugs: assessment of risks.
1987
[Hepatonephritis caused by piroxicam].
1987 Oct
[Fatal autoimmune hemolytic anemia probably induced by treatment with piroxicam].
1988 Mar 7
[Acute hemolytic anemia and hepatonephritis caused by piroxicam].
1988 Oct-Dec
Piroxicam-induced renal failure following relief of chronic retention.
1989 Apr
A comparison of tenoxicam and piroxicam in the treatment of rheumatoid arthritis.
1992 Apr
Anti-inflammatory effects of etodolac: comparison with other non-steroidal anti-inflammatory drugs.
1994 Dec
Tenidap in rheumatoid arthritis. A 24-week double-blind comparison with hydroxychloroquine-plus-piroxicam, and piroxicam alone.
1995 Oct
Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition.
1995 Sep 29
Differential effects of nonsteroidal anti-inflammatory drugs on constitutive and inducible prostaglandin G/H synthase in cultured bone cells.
1997 Aug
Nonsteroidal anti-inflammatory drugs enhance glutathione S-transferase theta levels in rat colon.
1998 Aug 24
[Cholestatic hepatitis associated with piroxicam use. Case report].
1998 May
Identification of HIV-1 integrase inhibitors based on a four-point pharmacophore.
1998 Nov
[Acute hepatic and renal failure due to piroxicam use].
2002 Mar
Altered expression of c-myc, p16 and p27 in rat colon tumors and its reversal by short-term treatment with chemopreventive agents.
2002 Sep
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Expression of cyclooxygenase-2 in primary superficial bladder cancer tissue may predict risk of its recurrence after complete transurethral resection.
2003 Jul
A novel mechanism of cyclooxygenase-2 inhibition involving interactions with Ser-530 and Tyr-385.
2003 Nov 14
Piroxicam gel, compared to EMLA cream is associated with less pain after venous cannulation in volunteers.
2003 Oct
[Generalized angioedema with capillary leak syndrome after piroxicam use: a case].
2003 Sep-Oct
Risk of serious upper gastrointestinal and cardiovascular thromboembolic complications with meloxicam.
2004 Jul 15
Effects of celecoxib on acid-challenged gastric mucosa of rats: comparison with metamizol and piroxicam.
2004 Jun
Mechanisms of protection by pantoprazole against NSAID-induced gastric mucosal damage.
2005 Jul
Apoptotic efficacy and inhibitory effect of dexamethasone on matrix metalloproteinase.
2005 Jul
Lansoprazole prevents experimental gastric injury induced by non-steroidal anti-inflammatory drugs through a reduction of mucosal oxidative damage.
2005 Jul 14
Oral aspirin challenges in patients with a history of intolerance to single non-steroidal anti-inflammatory drugs.
2005 Jun
Translational studies on aromatase, cyclooxygenases, and enzyme inhibitors in breast cancer.
2005 May
Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes.
2005 Nov
The effects of L-748706, a selective cyclooxygenase-2 inhibitor, on N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis.
2005 Sep
Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems.
2006 Aug
Direct binding of Cu(II)-complexes of oxicam NSAIDs with DNA backbone.
2006 Aug
Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents.
2006 Oct
Genetic susceptibility to nonsteroidal anti-inflammatory drug-related gastroduodenal bleeding: role of cytochrome P450 2C9 polymorphisms.
2007 Aug
Immunomodulatory effect of nonsteroidal anti-inflammatory drugs (NSAIDs) at the clinically available doses.
2007 Jan
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Effect of acetaminophen, a cyclooxygenase inhibitor, on Morris water maze task performance in mice.
2007 Sep
Piroxicam: restriction of indications: labelling change. Only half-measures.
2008 Oct
Antirheumatic drug response signatures in human chondrocytes: potential molecular targets to stimulate cartilage regeneration.
2009
The conversion of rapid TCCD nongenomic signals to persistent inflammatory effects via select protein kinases in MCF10A cells.
2009 Apr
Apoptosis induced by piroxicam plus cisplatin combined treatment is triggered by p21 in mesothelioma.
2011
Lung fibrosis induced by crystalline silica particles is uncoupled from lung inflammation in NMRI mice.
2011 Jun 10
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Patents

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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 Wed Jul 05 23:18:17 UTC 2023
Edited
by admin
on Wed Jul 05 23:18:17 UTC 2023
Record UNII
13T4O6VMAM
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
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
FELDENE
Brand 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 Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
WHO-VATC QS01BC06
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
NDF-RT N0000175722
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
WHO-ATC S01BC06
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
NCI_THESAURUS C1915
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
NCI_THESAURUS C1323
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
WHO-ATC M01AC01
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
WHO-ATC M02AA07
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
NDF-RT N0000000160
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
NDF-RT N0000175721
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
WHO-VATC QM02AA07
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
LIVERTOX NBK548425
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2210
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
DRUG BANK
DB00554
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
CHEBI
8249
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
FDA UNII
13T4O6VMAM
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
RXCUI
8356
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
MERCK INDEX
M8889
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID5021170
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
RS_ITEM_NUM
1544508
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
CAS
36322-90-4
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
IUPHAR
7273
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
ECHA (EC/EINECS)
252-974-3
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
NSC
666076
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
PUBCHEM
54676228
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
RXCUI
68115
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
ALTERNATIVE
SMS_ID
100000092492
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
EVMPD
SUB127114
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
LACTMED
Piroxicam
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
EVMPD
SUB09936MIG
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
WIKIPEDIA
PIROXICAM
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
INN
3713
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL527
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
NCI_THESAURUS
C751
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
MESH
D010894
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
DAILYMED
13T4O6VMAM
Created by admin on Wed Jul 05 23:18:17 UTC 2023 , Edited by admin on Wed Jul 05 23:18:17 UTC 2023
PRIMARY
Related Record Type Details
OAT-3
TRANSPORTER -> INHIBITOR
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
OAT-4
TRANSPORTER -> INHIBITOR
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
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
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ACCESSIBILITY
DISCLAIMER
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