Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H12N3O4S.K |
Molecular Weight | 369.437 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[K+].CN1C(C(=O)NC2=CC=CC=N2)=C([O-])C3=CC=CC=C3S1(=O)=O
InChI
InChIKey=YHKAIXSBBISJNM-UHFFFAOYSA-M
InChI=1S/C15H13N3O4S.K/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);/q;+1/p-1
DescriptionSources: http://www.drugbank.ca/drugs/DB00554Curator's Comment: Description was created based on several sources, including
https://www.pfizermedicalinformation.com/en-us/feldene
Sources: http://www.drugbank.ca/drugs/DB00554
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P04040 Gene ID: 847.0 Gene Symbol: CAT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16789438 |
0.414 mM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381057 |
4.4 µM [IC50] | ||
Target ID: Aminopeptidase activity Sources: https://www.ncbi.nlm.nih.gov/pubmed/26930569 |
70.0 µM [IC50] | ||
Target ID: CHEMBL1743319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25522350 |
73.8 µM [IC50] | ||
Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12511226 |
7.0 µM [IC50] | ||
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381057 |
1.3 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FELDENE Approved UseFELDENE 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 Date1982 |
|||
Primary | FELDENE Approved UseFELDENE 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 Date1982 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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%) Sources: Page: p.260Rash (0.74%) Vomiting (0.74%) Exanthema (0.74%) Injection site pain (0.74%) |
1800 mg single, oral Overdose |
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 Sources: Abdominal pain Gastric ulcer Duodenal ulcer |
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%) Sources: Page: p.158Haemorrhage of digestive tract (0.85%) Headache (0.85%) Oedema (0.85%) Pruritus (0.85%) Erythema facial (0.85%) |
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%) Sources: Page: p.233Diarrhoea (2.5%) Loose stools (2.5%) |
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) Sources: Page: p.1Myocardial 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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 |
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 |
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 |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Ki 20.5 uM] | ||||
yes [Ki 23 uM] | ||||
yes [Ki 4.88 uM] | ||||
yes [Ki 70.3 uM] | ||||
yes [Ki 84.9 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
[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 |
|
Aplastic anaemia associated with piroxicam. | 1991 Feb |
|
Zidovudine-induced macular edema. | 1991 Feb 15 |
|
Mechanism of anti-inflammatory action of fepradinol. | 1994 Jan |
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Antiinflammatory 4,5-diarylpyrroles. 2. Activity as a function of cyclooxygenase-2 inhibition. | 1995 Sep 29 |
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Differential effects of nonsteroidal anti-inflammatory drugs on constitutive and inducible prostaglandin G/H synthase in cultured bone cells. | 1997 Aug |
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Piroxicam and acarbose as chemopreventive agents for spontaneous intestinal adenomas in APC gene 1309 knockout mice. | 1998 Apr |
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Nonsteroidal anti-inflammatory drugs enhance glutathione S-transferase theta levels in rat colon. | 1998 Aug 24 |
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Transport of ochratoxin A by renal multispecific organic anion transporter 1. | 1999 Jun |
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A nonsteroidal anti-inflammatory drug, flufenamic acid, inhibits the expression of the androgen receptor in LNCaP cells. | 1999 Nov |
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Chemoprevention of vinyl carbamate-induced lung tumors in strain A mice. | 2000 Dec |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Polymorphic variants (CYP2C9*3 and CYP2C9*5) and the F114L active site mutation of CYP2C9: effect on atypical kinetic metabolism profiles. | 2002 Apr |
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[Acute hepatic and renal failure due to piroxicam use]. | 2002 Mar |
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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 |
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Protective role of cyclooxygenase (COX) inhibitors in burn-induced intestinal and liver damage. | 2002 May |
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Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs. | 2002 Oct 11 |
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Altered expression of c-myc, p16 and p27 in rat colon tumors and its reversal by short-term treatment with chemopreventive agents. | 2002 Sep |
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Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
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Effects of celecoxib on acid-challenged gastric mucosa of rats: comparison with metamizol and piroxicam. | 2004 Jun |
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Mechanisms of protection by pantoprazole against NSAID-induced gastric mucosal damage. | 2005 Jul |
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Apoptotic efficacy and inhibitory effect of dexamethasone on matrix metalloproteinase. | 2005 Jul |
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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 |
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Lansoprazole prevents experimental gastric injury induced by non-steroidal anti-inflammatory drugs through a reduction of mucosal oxidative damage. | 2005 Jul 14 |
|
Direct binding of Cu(II)-complexes of oxicam NSAIDs with DNA backbone. | 2006 Aug |
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Genetic susceptibility to nonsteroidal anti-inflammatory drug-related gastroduodenal bleeding: role of cytochrome P450 2C9 polymorphisms. | 2007 Aug |
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In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
Antirheumatic drug response signatures in human chondrocytes: potential molecular targets to stimulate cartilage regeneration. | 2009 |
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Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS). | 2009 Jun |
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Effects of cyclooxygenase inhibitor treatment on the renal toxicity of cisplatin in rats. | 2010 Feb |
|
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 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/piroxicam.html
Recommended dose: 20 mg orally once a day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11728432
Contractions induced by bradykinin in guinea-pig gallbladder smooth muscle strips were significantly attenuated by the cyclooxygenase inhibitor piroxicam (10 muM).
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S5XT2DB4P6
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100000166615
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164727-04-2
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SUB180790
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86278276
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ACTIVE MOIETY
SUBSTANCE RECORD