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

Approval Year

1982
100
Targets

Targets

Primary TargetPharmacologyConditionPotency
Catalase
6
Target ID: P04040
Gene ID: 847.0
Gene Symbol: CAT
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 0.414 mM [IC50]
Inhibitor
8297
 4.4 µM [IC50]
Inhibitor
8297
 70.0 µM [IC50]
Inhibitor
8297
 73.8 µM [IC50]
Inhibitor
8297
 7.0 µM [IC50]
Inhibitor
8297
 1.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
8429
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
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
1737
substrate
1037

inhibitor
1767
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
599

OAT2
145

OAT3
642

OAT4
146

Nav1.5
97
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT1
603
 yes [Ki 20.5 uM]
CYP2C9
1819
 yes [Ki 23 uM]
OAT3
644
 yes [Ki 4.88 uM]
OAT2
147
 yes [Ki 70.3 uM]
OAT4
146
 yes [Ki 84.9 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1037
 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
1737
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Nav1.5
100
hERG
1647
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
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
[Hepatonephritis caused by piroxicam].
1987 Oct
Piroxicam-induced renal failure following relief of chronic retention.
1989 Apr
Severe cholestatic jaundice associated with piroxicam.
1991 Dec
Aplastic anaemia associated with piroxicam.
1991 Feb
A comparison of tenoxicam and piroxicam in the treatment of rheumatoid arthritis.
1992 Apr
Nonsteroidal antiinflammatory drugs and certain rare, serious adverse events: a cohort study.
1993 May-Jun
Anti-inflammatory effects of etodolac: comparison with other non-steroidal anti-inflammatory drugs.
1994 Dec
Comparison of ketorolac tromethamine with other injectable nonsteroidal anti-inflammatory drugs for pain-on-injection and muscle damage in the rat.
1994 Feb
Tenidap in rheumatoid arthritis. A 24-week double-blind comparison with hydroxychloroquine-plus-piroxicam, and piroxicam alone.
1995 Oct
[Cholestatic hepatitis associated with piroxicam use. Case report].
1998 May
Identification of HIV-1 integrase inhibitors based on a four-point pharmacophore.
1998 Nov
Evaluation of 5-aminosalicylic acid (5-ASA) for cancer chemoprevention: lack of efficacy against nascent adenomatous polyps in the Apc(Min) mouse.
1999 Apr
Recurrent aseptic meningitis following non- steroidal anti-inflammatory drugs--a reminder.
1999 Dec
Transport of ochratoxin A by renal multispecific organic anion transporter 1.
1999 Jun
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes.
1999 May
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
A nonsteroidal anti-inflammatory drug, flufenamic acid, inhibits the expression of the androgen receptor in LNCaP cells.
1999 Nov
Leukotriene receptor antagonists may prevent NSAID-induced exacerbations in patients with chronic urticaria.
2000 Aug
Chemoprevention of vinyl carbamate-induced lung tumors in strain A mice.
2000 Dec
[Drug-induced toxic hearing loss (piroxicam and natural sulfo-conjugated estrogens): apropos of 2 case reports ].
2001
Eotaxin expression and eosinophil infiltrate in the liver of patients with drug-induced liver disease.
2001 Apr
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Polymorphic variants (CYP2C9*3 and CYP2C9*5) and the F114L active site mutation of CYP2C9: effect on atypical kinetic metabolism profiles.
2002 Apr
The clinical efficacy of piroxicam fast-dissolving dosage form for postoperative pain control after simple lumbar spine surgery: a double-blinded randomized study.
2002 Mar 1
Protective role of cyclooxygenase (COX) inhibitors in burn-induced intestinal and liver damage.
2002 May
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
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
Comparison of developmental toxicity of selective and non-selective cyclooxygenase-2 inhibitors in CRL:(WI)WUBR Wistar rats--DFU and piroxicam study.
2005 Jul 1
Lansoprazole prevents experimental gastric injury induced by non-steroidal anti-inflammatory drugs through a reduction of mucosal oxidative damage.
2005 Jul 14
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
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
The conversion of rapid TCCD nongenomic signals to persistent inflammatory effects via select protein kinases in MCF10A cells.
2009 Apr
Effects of cyclooxygenase inhibitor treatment on the renal toxicity of cisplatin in rats.
2010 Feb
Apoptosis induced by piroxicam plus cisplatin combined treatment is triggered by p21 in mesothelioma.
2011
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 Fri Dec 15 15:49:53 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:53 GMT 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 Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
WHO-VATC QS01BC06
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
NDF-RT N0000175722
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
WHO-ATC S01BC06
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
NCI_THESAURUS C1915
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
WHO-ATC M01AC01
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
WHO-ATC M02AA07
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
NDF-RT N0000000160
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
NDF-RT N0000175721
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
WHO-VATC QM02AA07
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
LIVERTOX NBK548425
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
Code System Code Type Description
DRUG CENTRAL
2210
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
DRUG BANK
DB00554
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
CHEBI
8249
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
FDA UNII
13T4O6VMAM
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
RXCUI
8356
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
MERCK INDEX
m8889
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID5021170
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
RS_ITEM_NUM
1544508
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
CAS
36322-90-4
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
IUPHAR
7273
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
ECHA (EC/EINECS)
252-974-3
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
NSC
666076
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
PUBCHEM
54676228
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
RXCUI
68115
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
ALTERNATIVE
SMS_ID
100000092492
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
EVMPD
SUB127114
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
LACTMED
Piroxicam
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
EVMPD
SUB09936MIG
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
WIKIPEDIA
PIROXICAM
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
INN
3713
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
ChEMBL
CHEMBL527
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
NCI_THESAURUS
C751
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
MESH
D010894
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
DAILYMED
13T4O6VMAM
Created by admin on Fri Dec 15 15:49:53 GMT 2023 , Edited by admin on Fri Dec 15 15:49:53 GMT 2023
PRIMARY
Related Record Type Details
OAT-3
TRANSPORTER -> INHIBITOR
OAT-2
TRANSPORTER -> INHIBITOR
Structure of PIROXICAM
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
OAT-4
TRANSPORTER -> INHIBITOR
Structure of PIROXICAM OLAMINE
SALT/SOLVATE -> PARENT
Structure of PIROXICAM
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
OAT-1
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
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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