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Details

Stereochemistry ACHIRAL
Molecular Formula C15H13N3O4S.H2O
Molecular Weight 349.3634
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIROXICAM MONOHYDRATE

SMILES

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

InChI

InChIKey=SDJQUPRVYCURBW-UHFFFAOYSA-N
InChI=1S/C15H13N3O4S.H2O/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);1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H13N3O4S
Molecular Weight 331.3481
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.

Originator

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

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
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
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
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
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: 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: 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: Page: p.260
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
unhealthy, 54
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
Sources:
Disc. AE: Nausea, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Nausea
Abdominal pain
Gastric ulcer
Duodenal ulcer
Sources:
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: 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: 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: 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: Page: p.233
unhealthy, >40
n = 40
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: >40
Sex: M+F
Population Size: 40
Sources: 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: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: Page: p.260
Abdominal pain Disc. AE
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
unhealthy, 54
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
Sources:
Duodenal ulcer Disc. AE
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
unhealthy, 54
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
Sources:
Gastric ulcer Disc. AE
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
unhealthy, 54
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
Sources:
Nausea Disc. AE
1800 mg single, oral
Overdose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
unhealthy, 54
n = 1
Health Status: unhealthy
Condition: Arthralgia
Age Group: 54
Sex: F
Population Size: 1
Sources:
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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: Page: p.233
unhealthy, >40
n = 40
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: >40
Sex: M+F
Population Size: 40
Sources: 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: Page: p.233
unhealthy, >40
n = 40
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: >40
Sex: M+F
Population Size: 40
Sources: 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: Page: p.233
unhealthy, >40
n = 40
Health Status: unhealthy
Condition: Osteoarthritis
Age Group: >40
Sex: M+F
Population Size: 40
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Osteoarthritis|Rheumatoid arthritis
Sources: Page: p.1
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

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

Tox targets

PubMed

PubMed

TitleDatePubMed
Piroxicam-induced renal failure and hyperkalemia.
1983 Jul
Piroxicam in acute musculoskeletal disorders and sport injuries.
1987
Severe cholestatic jaundice associated with piroxicam.
1991 Dec
Renal disease and use of topical non-steroidal anti-inflammatory drugs.
1994 Jan 8
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
Tenidap inhibits replication of the human immunodeficiency virus-1 in cultured cells.
1997 Jan 1
Piroxicam and acarbose as chemopreventive agents for spontaneous intestinal adenomas in APC gene 1309 knockout mice.
1998 Apr
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
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
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
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Expression of cyclooxygenase-2 in primary superficial bladder cancer tissue may predict risk of its recurrence after complete transurethral resection.
2003 Jul
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
Mechanisms of protection by pantoprazole against NSAID-induced gastric mucosal damage.
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
Direct binding of Cu(II)-complexes of oxicam NSAIDs with DNA backbone.
2006 Aug
Immunomodulatory effect of nonsteroidal anti-inflammatory drugs (NSAIDs) at the clinically available doses.
2007 Jan
Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS).
2009 Jun
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

Sample Use Guides

Recommended dose: 20 mg orally once a day
Route of Administration: Oral
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 Sat Jun 26 03:35:39 UTC 2021
Edited
by admin
on Sat Jun 26 03:35:39 UTC 2021
Record UNII
28MQO4N66D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIROXICAM MONOHYDRATE
Common Name English
2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE, 4-HYDROXY-2-METHYL-N-2-PYRIDINYL-, 1,1-DIOXIDE, HYDRATE (1:1)
Systematic Name English
2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE, 4-HYDROXY-2-METHYL-N-2-PYRIDINYL-, 1,1-DIOXIDE, MONOHYDRATE
Systematic Name English
Code System Code Type Description
PUBCHEM
54705052
Created by admin on Sat Jun 26 03:35:39 UTC 2021 , Edited by admin on Sat Jun 26 03:35:39 UTC 2021
PRIMARY
CAS
90936-70-2
Created by admin on Sat Jun 26 03:35:39 UTC 2021 , Edited by admin on Sat Jun 26 03:35:39 UTC 2021
PRIMARY
FDA UNII
28MQO4N66D
Created by admin on Sat Jun 26 03:35:39 UTC 2021 , Edited by admin on Sat Jun 26 03:35:39 UTC 2021
PRIMARY
EPA CompTox
90936-70-2
Created by admin on Sat Jun 26 03:35:39 UTC 2021 , Edited by admin on Sat Jun 26 03:35:39 UTC 2021
PRIMARY
Related Record Type Details
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