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Details

Stereochemistry ACHIRAL
Molecular Formula C15H13N3O4S
Molecular Weight 331.346
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIROXICAM

SMILES

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

InChI

InChIKey=QYSPLQLAKJAUJT-UHFFFAOYSA-N
InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)

HIDE SMILES / InChI
Molecular Formula C15H13N3O4S
Molecular Weight 331.346
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

1982
66
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7468
Arthritis, Rheumatoid
 1.3 µM [IC50]
Inhibitor
7468
 7.0 µM [IC50]
Inhibitor
7468
 73.8 µM [IC50]
Inhibitor
7468
 0.414 mM [IC50]
Inhibitor
7468
 70.0 µM [IC50]
Inhibitor
7468
Arthritis, Rheumatoid
 4.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cyclooxygenase-1
Cyclooxygenase-2
Approved
7883
FELDENE
Primary
Cyclooxygenase-1
Cyclooxygenase-2
Approved
7883
FELDENE
Approved (off-label)
8
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
Severe cholestatic jaundice associated with piroxicam.
1991 Dec
Zidovudine-induced macular edema.
1991 Feb 15
[Iatrogenic axonal neuropathy and erythroderma induced by piroxicam. Manifestations of hypersensitivity?].
1993
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
Mechanism of anti-inflammatory action of fepradinol.
1994 Jan
Renal disease and use of topical non-steroidal anti-inflammatory drugs.
1994 Jan 8
Fetal renal maldevelopment with oligohydramnios following maternal use of piroxicam.
1994 Oct
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
Tenidap inhibits replication of the human immunodeficiency virus-1 in cultured cells.
1997 Jan 1
Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity.
1997 Mar 14
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
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
Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes.
2005 Nov
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
Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS).
2009 Jun
Effects of cyclooxygenase inhibitor treatment on the renal toxicity of cisplatin in rats.
2010 Feb
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

JP2000327588A
7
JP2000501709A
69
JP2001039876A
13
JP2001503372A
24
JP2001525058A
66
JP2002128674A
4
JP2002128698A
5
JP2002193793A
4
JP2002511777A
372
JP2002513391A
22
JP2002521487A
13
JP2002528495A
37
JP2002533379A
51
JP2002541233A
365
JP2002544210A
84
JP2003252764A
4
JP2003503407A
6
JP2003515526A
422
JP2003528044A
28
JP2004175723A
6
JP2004269528A
25
JP2004523497A
72
JP2004534728A
69
JP2004534833A
5
JP2004536811A
30
JP2005525136A
18
JP2005535563A
58
JP2006500966A
18
JP2006506376A
4
JP2006515994A
13
JP2006523687A
25
JP2006524634A
45
JP2007238593A
4
JP2007503428A
34
JP2007508039A
97
JP2007508391A
16
JP2007512273A
10
JP2007513165A
52
JP2007514746A
6
JP2007514770A
72
JP2007515489A
10
JP2008504356A
28
JP2008505724A
4
JP2008539832A
67
JP2009525778A
32
JP2009525790A
86
JP2009533455A
13
JP2010506837A
73
JP2010525083A
41
JP2011006465A
4
JP2011500184A
33

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 Tue Oct 22 00:28:46 UTC 2019
Edited
by admin
on Tue Oct 22 00:28:46 UTC 2019
Record UNII
13T4O6VMAM
Record Status Validated (UNII)
Record Version
  • Download
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
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 [WHO-DD]
Common Name English
PIROXICAM ANHYDROUS
Common Name English
CP-16,171
Code English
PIROXICAM [EP]
Common Name English
PIROXICAM [USAN]
Common Name English
PIROXICAM [MART.]
Common Name English
PIROXICAM [USP]
Common Name English
PIROXICAM [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-VATC QM01AC01
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
WHO-VATC QS01BC06
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
NDF-RT N0000175722
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
WHO-ATC S01BC06
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
NCI_THESAURUS C1915
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
NCI_THESAURUS C1323
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
WHO-ATC M01AC01
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
WHO-ATC M02AA07
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
NDF-RT N0000000160
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
NDF-RT N0000175721
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
WHO-VATC QM02AA07
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
LIVERTOX 782
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
Code System Code Type Description
DRUG BANK
DB00554
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
RXCUI
8356
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
MERCK INDEX
M8889
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY Merck Index
EPA CompTox
36322-90-4
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
CAS
36322-90-4
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
IUPHAR
7273
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
ECHA (EC/EINECS)
252-974-3
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
PUBCHEM
54676228
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
RXCUI
68115
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
ALTERNATIVE
EVMPD
SUB127114
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
EVMPD
SUB09936MIG
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
WIKIPEDIA
PIROXICAM
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
INN
3713
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
ChEMBL
CHEMBL527
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
NCI_THESAURUS
C751
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
LactMed
36322-90-4
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
MESH
D010894
Created by admin on Tue Oct 22 00:28:46 UTC 2019 , Edited by admin on Tue Oct 22 00:28:46 UTC 2019
PRIMARY
Related Record Type Details
OAT-3
TRANSPORTER -> INHIBITOR
OAT-2
TRANSPORTER -> INHIBITOR
Structure of PIROXICAM
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
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
Structure of PIROXICAM MONOHYDRATE
SALT/SOLVATE -> PARENT
OAT-4
TRANSPORTER -> INHIBITOR
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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