You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NamePiroxicam
Accession NumberDB00554  (APRD01187)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily. [PubChem]

Structure
Thumb
Synonyms
4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid
Feldene
Piroxicam
Piroxicamum
Pyroxycam
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alti-piroxicam-cap 10mgcapsule10 mgoralAltimed Pharma Inc.1997-09-242004-08-03Canada
Alti-piroxicam-cap 20mgcapsule20 mgoralAltimed Pharma Inc.1995-12-312004-08-03Canada
Dom-piroxicamcapsule20 mgoralDominion Pharmacal1999-10-25Not applicableCanada
Dom-piroxicamcapsule10 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-piroxicamsuppository20 mgrectalDominion Pharmacal1995-12-31Not applicableCanada
Dom-piroxicamsuppository10 mgrectalDominion Pharmacal1995-12-31Not applicableCanada
Feldenecapsule10 mg/1oralPfizer Laboratories Div Pfizer Inc1994-05-25Not applicableUs
Feldenecapsule20 mg/1oralREMEDYREPACK INC.2012-09-26Not applicableUs
Feldenecapsule20 mg/1oralPfizer Laboratories Div Pfizer Inc1994-05-25Not applicableUs
Feldene Cap 10mgcapsule10 mgoralPfizer Canada Inc1981-12-312002-09-06Canada
Feldene Cap 20mgcapsule20 mgoralPfizer Canada Inc1981-12-312002-07-25Canada
Feldene Sup 10mgsuppository10 mgrectalPfizer Canada Inc1986-12-311999-08-10Canada
Feldene Sup 20mgsuppository20 mgrectalPfizer Canada Inc1986-12-312002-07-25Canada
Fexicamsuppository20 mgrectalTechnilab Pharma Inc.1998-08-172004-08-03Canada
Gen-piroxicam - Cap 20mgcapsule20 mgoralGenpharm Ulc1995-12-312010-08-04Canada
Gen-piroxicam-cap 10mgcapsule10 mgoralGenpharm Ulc1995-12-312010-08-04Canada
Nu-pirox Cap 10mgcapsule10 mgoralNu Pharm Inc1990-12-312012-09-04Canada
Nu-pirox Cap 20mgcapsule20 mgoralNu Pharm Inc1990-12-312012-09-04Canada
Penta-piroxicam Capsulescapsule20 mgoralPentapharm Ltd.Not applicableNot applicableCanada
Penta-piroxicam Capsulescapsule10 mgoralPentapharm Ltd.Not applicableNot applicableCanada
Piroxicamcapsule20 mg/1oralGreenstone LLC2014-03-03Not applicableUs
Piroxicamcapsule10 mg/1oralGreenstone LLC2014-03-03Not applicableUs
Piroxicam Capsules 10mgcapsule10 mgoralPrempharm Inc1997-01-052005-08-05Canada
Piroxicam Capsules 20mgcapsule20 mgoralPrempharm Inc1997-01-052005-08-05Canada
PMS-piroxicamcapsule10 mgoralPharmascience Inc1996-12-31Not applicableCanada
PMS-piroxicamcapsule20 mgoralPharmascience Inc1996-12-31Not applicableCanada
PMS-piroxicam Suppositories -20mgsuppository20 mgrectalPharmascience Inc1995-12-31Not applicableCanada
PMS-piroxicam Suppositories-10mgsuppository10 mgrectalPharmascience Inc1995-12-31Not applicableCanada
Pro-piroxicam Cap 10mgtablet10 mgoralPro Doc Limitee1987-12-312010-07-13Canada
Pro-piroxicam Cap 20mgcapsule20 mgoralPro Doc Limitee1987-12-312010-07-13Canada
Rho-piroxicam - 10mg Capcapsule10 mgoralRhodiapharm Inc1995-12-311998-08-05Canada
Rho-piroxicam - Cap 20mgcapsule20 mgoralRhodiapharm Inc1995-12-311998-08-05Canada
Teva-piroxicamcapsule10 mgoralTeva Canada Limited1986-12-31Not applicableCanada
Teva-piroxicamcapsule20 mgoralTeva Canada Limited1986-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Piroxicam Cap 10mgcapsule10 mgoralApotex Inc1986-12-31Not applicableCanada
Apo Piroxicam Cap 20mgcapsule20 mgoralApotex Inc1986-12-31Not applicableCanada
Feldenecapsule20 mg/1oralKeltman Pharmaceuticals Inc.2007-09-18Not applicableUs
Piroxicamcapsule20 mg/1oralGolden State Medical Supply, Inc.2010-01-05Not applicableUs
Piroxicamcapsule10 mg/1oralAv Kare, Inc.2013-06-27Not applicableUs
Piroxicamcapsule10 mg/1oralTeva Pharmaceuticals USA Inc1994-10-19Not applicableUs
Piroxicamcapsule20 mg/1oralbryant ranch prepack2010-01-05Not applicableUs
Piroxicamcapsule20 mg/1oralSTAT Rx USA LLC2011-10-07Not applicableUs
Piroxicamcapsule10 mg/1oralAvera Mc Kennan Hospital2015-11-10Not applicableUs
Piroxicamcapsule20 mg/1oralA S Medication Solutions Llc2010-01-05Not applicableUs
Piroxicamcapsule20 mg/1oralRebel Distributors Corp2009-11-12Not applicableUs
Piroxicamcapsule10 mg/1oralGolden State Medical Supply, Inc.2010-01-05Not applicableUs
Piroxicamcapsule10 mg/1oralRebel Distributors Corp2010-01-05Not applicableUs
Piroxicamcapsule10 mg/1oralH.J. Harkins Company, Inc.2012-04-16Not applicableUs
Piroxicamcapsule20 mg/1oralSTAT Rx USA LLC2010-11-02Not applicableUs
Piroxicamcapsule20 mg/1oralSun Pharmaceutical Industries, Inc.1993-03-12Not applicableUs
Piroxicamcapsule20 mg/1oralRebel Distributors Corp2010-01-05Not applicableUs
Piroxicamcapsule20 mg/1oralH.J. Harkins Company, Inc.2012-04-16Not applicableUs
Piroxicamcapsule10 mg/1oralSTAT Rx USA LLC2010-11-02Not applicableUs
Piroxicamcapsule10 mg/1oralSun Pharmaceutical Industries, Inc.1993-03-12Not applicableUs
Piroxicamcapsule20 mg/1oralNostrum Laboratories, Inc.2010-01-05Not applicableUs
Piroxicamcapsule20 mg/1oralUnit Dose Services2010-01-05Not applicableUs
Piroxicamcapsule20 mg/1oralPACK Pharmaceuticals, LLC2010-06-15Not applicableUs
Piroxicamcapsule10 mg/1oralNostrum Laboratories, Inc.2010-01-05Not applicableUs
Piroxicamcapsule20 mg/1oralPd Rx Pharmaceuticals, Inc.2010-11-02Not applicableUs
Piroxicamcapsule10 mg/1oralPACK Pharmaceuticals, LLC2010-06-15Not applicableUs
Piroxicamcapsule20 mg/1oralAphena Pharma Solutions Tennessee, Llc1994-01-26Not applicableUs
Piroxicamcapsule20 mg/1oralLake Erie Medical DBA Quality Care Products LLC1994-01-26Not applicableUs
Piroxicamcapsule10 mg/1oralREMEDYREPACK INC.2013-03-20Not applicableUs
Piroxicamcapsule20 mg/1oralPhysicians Total Care, Inc.1994-10-06Not applicableUs
Piroxicamcapsule20 mg/1oralDIRECT RX2014-01-01Not applicableUs
Piroxicamcapsule20 mg/1oralAv Kare, Inc.2012-11-28Not applicableUs
Piroxicamcapsule20 mg/1oralTeva Pharmaceuticals USA Inc1994-01-26Not applicableUs
Piroxicamcapsule10 mg/1oralbryant ranch prepack2010-01-05Not applicableUs
Piroxicamcapsule20 mg/1oralREMEDYREPACK INC.2011-04-12Not applicableUs
Piroxicamcapsule10 mg/1oralPhysicians Total Care, Inc.2005-01-21Not applicableUs
Piroxicamcapsule10 mg/1oralRebel Distributors Corp2009-11-12Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Piroxicamcapsule10 mg/1oralNorthstar Rx LLC2016-02-152016-03-19Us
Piroxicamcapsule20 mg/1oralNivagen Pharmaceuticals, Inc2016-02-152016-03-29Us
Piroxicamcapsule10 mg/1oralNivagen Pharmaceuticals, Inc2016-02-152016-03-29Us
Piroxicamcapsule20 mg/1oralNorthstar Rx LLC2016-02-152016-03-19Us
International Brands
NameCompany
BruxicamNot Available
DolonexNot Available
ErazonNot Available
GeldèneNot Available
ImprontalNot Available
RoxamBosnalijek
RoxidenNot Available
SasulenNot Available
SolocalmNot Available
TrastNot Available
Brand mixtures
NameLabellerIngredients
TherafeldaminePhysician Therapeutics Llc
SaltsNot Available
Categories
UNII13T4O6VMAM
CAS number36322-90-4
WeightAverage: 331.346
Monoisotopic: 331.062676609
Chemical FormulaC15H13N3O4S
InChI KeyInChIKey=QYSPLQLAKJAUJT-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboxamide
SMILES
CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassNot Available
Direct ParentBenzothiazines
Alternative Parents
Substituents
  • N-arylamide
  • Benzothiazine
  • Aminopyridine
  • Imidolactam
  • Benzenoid
  • Pyridine
  • Ortho-thiazine
  • Heteroaromatic compound
  • Vinylogous acid
  • Sulfonic acid derivative
  • Sulfonamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor treatment of osteoarthritis and rheumatoid arthritis.
PharmacodynamicsPiroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). 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.
Mechanism of actionThe 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.
Related Articles
AbsorptionWell absorbed following oral administration.
Volume of distribution
  • 0.14 L/kg
Protein bindingNot Available
Metabolism

Renal

SubstrateEnzymesProduct
Piroxicam
5'-HydroxypiroxicamDetails
Route of eliminationPiroxicam and its biotransformation products are excreted in urine and feces, with about twice as much appearing in the urine as in the feces. Approximately 5% of a piroxicam dose is excreted unchanged. However, a substantial portion of piroxicam elimination occurs by hepatic metabolism. Piroxicam is excreted into human milk.
Half life30 to 86 hours
ClearanceNot Available
ToxicitySymptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Piroxicam Action PathwayDrug actionSMP00077
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9898
Blood Brain Barrier-0.9659
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5786
P-glycoprotein inhibitor INon-inhibitor0.7285
P-glycoprotein inhibitor IINon-inhibitor0.7453
Renal organic cation transporterNon-inhibitor0.9437
CYP450 2C9 substrateSubstrate0.6437
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7356
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.9086
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8789
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8709
Ames testNon AMES toxic0.8767
CarcinogenicityNon-carcinogens0.7612
BiodegradationNot ready biodegradable0.923
Rat acute toxicity3.1545 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9589
hERG inhibition (predictor II)Non-inhibitor0.8311
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Akorn inc
  • Pfizer laboratories div pfizer inc
  • Egis pharmaceuticals
  • Genpharm pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Nostrum laboratories inc
  • Roxane laboratories inc
  • Scs pharmaceuticals
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral10 mg/1
Capsuleoral20 mg/1
Capsuleoral10 mg
Capsuleoral20 mg
Suppositoryrectal20 mg
Suppositoryrectal10 mg
Tabletoral10 mg
Kit
Prices
Unit descriptionCostUnit
Piroxicam powder13.16USD g
Akten 3.5% drops7.5USD ml
Feldene 20 mg capsule4.93USD capsule
Feldene 10 mg capsule2.82USD capsule
Piroxicam 20 mg capsule2.69USD capsule
Pms-Piroxicam 20 mg Suppository1.82USD suppository
Piroxicam 10 mg capsule1.44USD capsule
Apo-Piroxicam 20 mg Capsule0.75USD capsule
Novo-Pirocam 20 mg Capsule0.75USD capsule
Nu-Pirox 20 mg Capsule0.75USD capsule
Apo-Piroxicam 10 mg Capsule0.43USD capsule
Gen-Piroxicam 10 mg Capsule0.43USD capsule
Novo-Pirocam 10 mg Capsule0.43USD capsule
Nu-Pirox 10 mg Capsule0.43USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point198-200 °CPhysProp
water solubility23 mg/L (at 22 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.06AVDEEF,A (1997)
logS-4.16ADME Research, USCD
Caco2 permeability-4.45ADME Research, USCD
pKa6.3SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.143 mg/mLALOGPS
logP2.2ALOGPS
logP0.6ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.76ChemAxon
pKa (Strongest Basic)3.79ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity87.04 m3·mol-1ChemAxon
Polarizability32.27 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Paul D. Weeks, “3-Hydroxy 2-methyl benzisothiazolines as intermediates in production of piroxicam.” U.S. Patent US4376204, issued April, 1982.

US4376204
General ReferencesNot Available
External Links
ATC CodesM02AA07S01BC06M01AC01
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelDownload (74.3 KB)
MSDSDownload (73.3 KB)
Interactions
Drug Interactions
Drug
AbciximabPiroxicam may increase the anticoagulant activities of Abciximab.
AcenocoumarolPiroxicam may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Piroxicam is combined with Acetylsalicylic acid.
AliskirenPiroxicam may decrease the antihypertensive activities of Aliskiren.
AlteplasePiroxicam may increase the anticoagulant activities of Alteplase.
AmikacinPiroxicam may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmitriptylineAmitriptyline may increase the antiplatelet activities of Piroxicam.
AnistreplasePiroxicam may increase the anticoagulant activities of Anistreplase.
ApixabanThe risk or severity of adverse effects can be increased when Piroxicam is combined with Apixaban.
ArbekacinPiroxicam may decrease the excretion rate of Arbekacin which could result in a lower serum level and potentially a reduction in efficacy.
BalsalazidePiroxicam may increase the nephrotoxic activities of Balsalazide.
CeritinibThe serum concentration of Piroxicam can be increased when it is combined with Ceritinib.
Citric AcidPiroxicam may increase the anticoagulant activities of Citric Acid.
ColesevelamColesevelam can cause a decrease in the absorption of Piroxicam resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Piroxicam is combined with Collagenase.
CyclosporinePiroxicam may increase the nephrotoxic activities of Cyclosporine.
Dabigatran etexilatePiroxicam may increase the anticoagulant activities of Dabigatran etexilate.
DabrafenibThe serum concentration of Piroxicam can be decreased when it is combined with Dabrafenib.
DalteparinPiroxicam may increase the anticoagulant activities of Dalteparin.
DasatinibDasatinib may increase the anticoagulant activities of Piroxicam.
DeferasiroxThe risk or severity of adverse effects can be increased when Piroxicam is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Piroxicam is combined with Deoxycholic Acid.
DesmopressinThe risk or severity of adverse effects can be increased when Piroxicam is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Piroxicam.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Piroxicam.
DicoumarolPiroxicam may increase the anticoagulant activities of Dicoumarol.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Piroxicam.
DrospirenonePiroxicam may increase the hyperkalemic activities of Drospirenone.
Edetic AcidPiroxicam may increase the anticoagulant activities of Edetic Acid.
EnoxaparinPiroxicam may increase the anticoagulant activities of Enoxaparin.
EplerenonePiroxicam may decrease the antihypertensive activities of Eplerenone.
Ethyl biscoumacetatePiroxicam may increase the anticoagulant activities of Ethyl biscoumacetate.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Piroxicam.
FloxuridineThe metabolism of Piroxicam can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Piroxicam can be decreased when combined with Fluconazole.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Piroxicam.
Fondaparinux sodiumPiroxicam may increase the anticoagulant activities of Fondaparinux sodium.
FramycetinPiroxicam may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
GentamicinPiroxicam may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
GlucosamineGlucosamine may increase the antiplatelet activities of Piroxicam.
HaloperidolThe risk or severity of adverse effects can be increased when Piroxicam is combined with Haloperidol.
HeparinPiroxicam may increase the anticoagulant activities of Heparin.
HydralazinePiroxicam may decrease the antihypertensive activities of Hydralazine.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Piroxicam is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Piroxicam.
IcosapentThe risk or severity of adverse effects can be increased when Piroxicam is combined with Icosapent.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Piroxicam.
KanamycinPiroxicam may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Piroxicam.
LimaprostLimaprost may increase the antiplatelet activities of Piroxicam.
LithiumThe serum concentration of Lithium can be increased when it is combined with Piroxicam.
LumacaftorThe serum concentration of Piroxicam can be decreased when it is combined with Lumacaftor.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Piroxicam.
MifepristoneThe serum concentration of Piroxicam can be increased when it is combined with Mifepristone.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Piroxicam.
NadololPiroxicam may decrease the antihypertensive activities of Nadolol.
NeomycinPiroxicam may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NetilmicinPiroxicam may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
ObinutuzumabThe risk or severity of adverse effects can be increased when Piroxicam is combined with Obinutuzumab.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Piroxicam is combined with Homoharringtonine.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Piroxicam.
PamidronateThe risk or severity of adverse effects can be increased when Piroxicam is combined with Pamidronate.
ParoxetineParoxetine may increase the antiplatelet activities of Piroxicam.
PemetrexedThe serum concentration of Pemetrexed can be increased when it is combined with Piroxicam.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Piroxicam.
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Piroxicam.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Piroxicam.
PhenindionePiroxicam may increase the anticoagulant activities of Phenindione.
PhenprocoumonPiroxicam may increase the anticoagulant activities of Phenprocoumon.
PhenytoinThe metabolism of Piroxicam can be increased when combined with Phenytoin.
PorfimerPiroxicam may increase the photosensitizing activities of Porfimer.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Piroxicam.
ProbenecidThe serum concentration of Piroxicam can be increased when it is combined with Probenecid.
ReteplasePiroxicam may increase the anticoagulant activities of Reteplase.
RibostamycinPiroxicam may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RidogrelPiroxicam may increase the anticoagulant activities of Ridogrel.
RivaroxabanPiroxicam may increase the anticoagulant activities of Rivaroxaban.
SecobarbitalThe metabolism of Piroxicam can be increased when combined with Secobarbital.
SparfloxacinPiroxicam may increase the neuroexcitatory activities of Sparfloxacin.
SpectinomycinPiroxicam may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptokinasePiroxicam may increase the anticoagulant activities of Streptokinase.
StreptomycinPiroxicam may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
SulfisoxazoleThe metabolism of Piroxicam can be decreased when combined with Sulfisoxazole.
SulodexidePiroxicam may increase the anticoagulant activities of Sulodexide.
TacrolimusPiroxicam may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Piroxicam.
TenecteplasePiroxicam may increase the anticoagulant activities of Tenecteplase.
TenofovirThe risk or severity of adverse effects can be increased when Piroxicam is combined with Tenofovir.
TipranavirTipranavir may increase the antiplatelet activities of Piroxicam.
TobramycinPiroxicam may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemidePiroxicam may decrease the diuretic activities of Torasemide.
TositumomabThe risk or severity of adverse effects can be increased when Piroxicam is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Piroxicam.
TriamterenePiroxicam may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Piroxicam.
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Piroxicam.
UrokinasePiroxicam may increase the anticoagulant activities of Urokinase.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Piroxicam.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Piroxicam.
VenlafaxineVenlafaxine may increase the antiplatelet activities of Piroxicam.
VerteporfinPiroxicam may increase the photosensitizing activities of Verteporfin.
Vitamin EVitamin E may increase the antiplatelet activities of Piroxicam.
WarfarinPiroxicam may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Take with food. Avoid alcohol.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed:10381057 ]
  2. Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [PubMed:11785774 ]
  3. Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [PubMed:11153163 ]
  4. Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [PubMed:11952155 ]
  5. Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [PubMed:15464832 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed:10381057 ]
  2. Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [PubMed:11785774 ]
  3. Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [PubMed:11153163 ]
  4. Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [PubMed:11952155 ]
  5. Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [PubMed:15464832 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. [PubMed:9275312 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
  2. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456 ]
  3. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
  4. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]
  5. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. [PubMed:10336520 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456 ]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
  3. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [PubMed:10224140 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular Weight:
59970.945 Da
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169 ]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23