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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
SynonymLanguageCode
4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxidNot AvailableNot Available
FeldeneNot AvailableNot Available
PiroxicamNot AvailableNot Available
PiroxicamumNot AvailableNot Available
PyroxycamNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Feldenecapsule10 mgoralPfizer Laboratories Div Pfizer Inc1994-05-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Feldenecapsule20 mgoralPfizer Laboratories Div Pfizer Inc1994-05-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Feldenecapsule20 mgoralREMEDYREPACK INC.2012-09-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralGreenstone LLC2014-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralGreenstone LLC2014-03-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Piroxicamcapsule10 mgoralTeva Pharmaceuticals USA Inc1994-10-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralTeva Pharmaceuticals USA Inc1994-01-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralPACK Pharmaceuticals, LLC2010-06-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralPACK Pharmaceuticals, LLC2010-06-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralSTAT Rx USA LLC2010-11-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralSTAT Rx USA LLC2010-11-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralRebel Distributors Corp2009-11-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralRebel Distributors Corp2009-11-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralREMEDYREPACK INC.2013-03-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralNostrum Laboratories, Inc.2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralNostrum Laboratories, Inc.2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralRebel Distributors Corp2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralRebel Distributors Corp2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralAv Kare, Inc.2013-06-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralAv Kare, Inc.2012-11-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralSTAT Rx USA LLC2011-10-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralREMEDYREPACK INC.2011-04-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralREMEDYREPACK INC.2011-04-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralLake Erie Medical DBA Quality Care Products LLC1994-01-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralUnit Dose Services2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralH.J. Harkins Company, Inc.2012-04-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralH.J. Harkins Company, Inc.2012-04-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralA S Medication Solutions Llc2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralPhysicians Total Care, Inc.2005-01-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralPhysicians Total Care, Inc.1994-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralPd Rx Pharmaceuticals, Inc.2010-11-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralGolden State Medical Supply, Inc.2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralGolden State Medical Supply, Inc.2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralDIRECT RX2014-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralbryant ranch prepack2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule10 mgoralbryant ranch prepack2010-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Piroxicamcapsule20 mgoralAphena Pharma Solutions Tennessee, Llc1994-01-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Feldenecapsule20 mgoralKeltman Pharmaceuticals Inc.2007-09-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
BruxicamNot Available
DolonexNot Available
ErazonNot Available
GeldèneNot Available
ImprontalNot Available
RoxamBosnalijek
RoxidenNot Available
SasulenNot Available
SolocalmNot Available
TrastNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number36322-90-4
WeightAverage: 331.346
Monoisotopic: 331.062676609
Chemical FormulaC15H13N3O4S
InChI KeyQYSPLQLAKJAUJT-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.
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 substrateInhibitor0.9086
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-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
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
Capsuleoral20 mg
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
SpectraNot 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 ReferenceNot Available
External Links
ATC CodesM01AC01M02AA07S01BC06
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelDownload (74.3 KB)
MSDSDownload (73.3 KB)
Interactions
Drug Interactions
Drug
AbciximabAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
AcenocoumarolAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Acetylsalicylic acidNSAID (Nonselective) may enhance the adverse/toxic effect of Salicylates. An increased risk of bleeding may be associated with use of this combination. NSAID (Nonselective) may diminish the cardioprotective effect of Salicylates. Salicylates may decrease the serum concentration of NSAID (Nonselective). Exceptions: Choline Magnesium Trisalicylate.
AliskirenNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of Aliskiren. Nonsteroidal Anti-Inflammatory Agents may enhance the nephrotoxic effect of Aliskiren.
AlteplaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
AmikacinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
AnistreplaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
ApixabanAgents with Antiplatelet Properties may enhance the adverse/toxic effect of Apixaban. Specifically, the risk for bleeding may be increased.
ArbekacinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
Citric AcidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
ColesevelamMay decrease the absorption of Nonsteroidal Anti-Inflammatory Agents.
Dabigatran etexilateAgents with Antiplatelet Properties may enhance the anticoagulant effect of Dabigatran Etexilate. Agents with Antiplatelet Properties may increase the serum concentration of Dabigatran Etexilate. This mechanism applies specifically to clopidogrel.
DabrafenibMay decrease the serum concentration of CYP2C9 Substrates.
DalteparinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DasatinibMay enhance the anticoagulant effect of Agents with Antiplatelet Properties.
DeferasiroxNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
Deoxycholic AcidAgents with Antiplatelet Properties may enhance the adverse/toxic effect of Deoxycholic Acid. Specifically, the risk for bleeding or bruising in the treatment area may be increased.
DesmopressinNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Desmopressin.
DicoumarolAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DigoxinNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Digoxin.
Edetic AcidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EnoxaparinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EplerenoneNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of Eplerenone. Nonsteroidal Anti-Inflammatory Agents may enhance the hyperkalemic effect of Eplerenone.
Ethyl biscoumacetateAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FloctafenineMay enhance the adverse/toxic effect of Nonsteroidal Anti-Inflammatory Agents.
Fondaparinux sodiumAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FramycetinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
GentamicinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
GlucosamineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
HaloperidolNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Haloperidol. Specifically including drowsiness and confusion.
HeparinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
HydralazineNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of HydrALAZINE.
IbritumomabAgents with Antiplatelet Properties may enhance the adverse/toxic effect of Ibritumomab. Both agents may contribute to impaired platelet function and an increased risk of bleeding.
KanamycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
LithiumNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Lithium.
MethotrexateNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Methotrexate.
MifepristoneMay increase the serum concentration of CYP2C9 Substrates.
NeomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
NetilmicinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
ObinutuzumabAgents with Antiplatelet Properties may enhance the adverse/toxic effect of Obinutuzumab. Specifically, the risk of serious bleeding-related events may be increased.
PemetrexedNSAID (Nonselective) may increase the serum concentration of PEMEtrexed.
PentoxifyllineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
PhenindioneAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
PhenprocoumonAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
PorfimerPhotosensitizing Agents may enhance the photosensitizing effect of Porfimer.
PralatrexateNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of PRALAtrexate. More specifically, NSAIDS may decrease the renal excretion of pralatrexate.
ProbenecidMay increase the serum concentration of Nonsteroidal Anti-Inflammatory Agents.
ReteplaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
RibostamycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
RidogrelAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
RivaroxabanAgents with Antiplatelet Properties may enhance the anticoagulant effect of Rivaroxaban.
Salicylate-sodiumNSAID (Nonselective) may enhance the adverse/toxic effect of Salicylates. An increased risk of bleeding may be associated with use of this combination. NSAID (Nonselective) may diminish the cardioprotective effect of Salicylates. Salicylates may decrease the serum concentration of NSAID (Nonselective). Exceptions: Choline Magnesium Trisalicylate.
SpectinomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
StreptokinaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
StreptomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
SulodexideAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TenecteplaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
TenofovirNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Tenofovir.
TipranavirMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
TobramycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TreprostinilAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
UrokinaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
VancomycinNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Vancomycin.
VerteporfinPhotosensitizing Agents may enhance the photosensitizing effect of Verteporfin.
Vitamin EMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
WarfarinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Food Interactions
  • Take with food. Avoid alcohol.

Targets

1. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

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
  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
  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
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

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
  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
  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
  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
  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

Enzymes

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. 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
  4. 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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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. Epub 2009 Nov 24. Pubmed

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. Pubmed

Transporters

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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
  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
  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
  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
  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

2. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

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
  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
  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

3. Solute carrier family 22 member 11

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 11 Q9NSA0 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11