Identification

Name
Piroxicam
Accession Number
DB00554  (APRD01187)
Type
Small Molecule
Groups
Approved, 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
  • Piroxicam
  • Piroxicam betadex
  • Piroxicamum
  • Pyroxycam
External IDs
CP-16,171
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Piroxicam Cap 10mgCapsule10 mgOralApotex Corporation1986-12-31Not applicableCanada
Apo Piroxicam Cap 20mgCapsule20 mgOralApotex Corporation1986-12-31Not applicableCanada
FeldeneCapsule20 mg/1OralPfizer Laboratories Div Pfizer Inc1994-05-25Not applicableUs
FeldeneCapsule20 mg/1OralRemedy Repack2012-07-192013-08-20Us
FeldeneCapsule10 mg/1OralPfizer Laboratories Div Pfizer Inc1994-05-25Not applicableUs
FeldeneCapsule20 mg/1OralPhysicians Total Care, Inc.1994-05-252012-06-30Us
Feldene Cap 10mgCapsule10 mgOralPfizer1981-12-312002-09-06Canada
Feldene Cap 20mgCapsule20 mgOralPfizer1981-12-312002-07-25Canada
Feldene Sup 10mgSuppository10 mgRectalPfizer1986-12-311999-08-10Canada
Feldene Sup 20mgSuppository20 mgRectalPfizer1986-12-312002-07-25Canada
Generic 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 Pharmacal1999-10-252016-10-25Canada
Dom-piroxicamSuppository10 mgRectalDominion Pharmacal1995-12-312016-10-25Canada
Dom-piroxicamCapsule10 mgOralDominion PharmacalNot applicable2016-10-25Canada
Dom-piroxicamSuppository20 mgRectalDominion Pharmacal1995-12-312016-10-25Canada
FeldeneCapsule20 mg/1OralKeltman Pharmaceuticals Inc.2007-09-18Not applicableUs
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
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
TherafeldaminePiroxicam (20 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-03-03Not applicableUs
International/Other Brands
Bruxicam / Dolonex / Erazon / Feldene / Geldène / Improntal / Roxam (Bosnalijek) / Roxiden / Sasulen / Solocalm / Trast
Categories
UNII
13T4O6VMAM
CAS number
36322-90-4
Weight
Average: 331.346
Monoisotopic: 331.062676609
Chemical Formula
C15H13N3O4S
InChI Key
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

Pharmacology

Indication

For treatment of osteoarthritis and rheumatoid arthritis.

Associated Conditions
Pharmacodynamics

Piroxicam 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 action

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.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Human
UProstaglandin G/H synthase 1
inhibitor
Human
Absorption

Well absorbed following oral administration.

Volume of distribution
  • 0.14 L/kg
Protein binding
Not Available
Metabolism

Renal

Route of elimination

Piroxicam 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 life

30 to 86 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Piroxicam Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*3Not Available1075A>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Piroxicam is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Piroxicam is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Piroxicam is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Piroxicam is combined with 4-hydroxycoumarin.
AbacavirPiroxicam may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Piroxicam is combined with Abciximab.
AbirateroneThe metabolism of Piroxicam can be decreased when combined with Abiraterone.
AcarbosePiroxicam may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololPiroxicam may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Piroxicam is combined with Aceclofenac.
Food Interactions
  • Take with food. Avoid alcohol.

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 References
Not Available
External Links
Human Metabolome Database
HMDB0014694
KEGG Drug
D00127
KEGG Compound
C01608
PubChem Compound
54676228
PubChem Substance
46505225
ChemSpider
10442653
BindingDB
85245
ChEBI
8249
ChEMBL
CHEMBL527
Therapeutic Targets Database
DAP000181
PharmGKB
PA450985
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Piroxicam
ATC Codes
M02AA07 — PiroxicamS01BC06 — PiroxicamM01AC01 — Piroxicam
AHFS Codes
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
FDA label
Download (74.3 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingPreventionPulpitis - Irreversible1
1, 2RecruitingTreatmentRenal Colic1
2CompletedNot AvailablePostcoital Contraception1
2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2, 3RecruitingTreatmentEmergency Contraception1
4CompletedSupportive CareCytochrome P450 CYP2C9 Enzyme Deficiency / Impacted Third Molar Tooth / Other Surgical Procedures / Pain NOS1
4CompletedTreatmentDysmenorrhea1
4CompletedTreatmentHigh Blood Pressure (Hypertension)1
4CompletedTreatmentPrimary Dysmenorrhoea1
Not AvailableCompletedDiagnosticDermatitis, Photocontact1
Not AvailableNot Yet RecruitingTreatmentPostoperative pain1

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
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Akorn Inc.
  • Amerisource Health Services Corp.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Corepharma LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Egis Pharmaceuticals Public Ltd. Co.
  • Goldline Laboratories Inc.
  • Group Health Cooperative
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Medisca Inc.
  • Mepha Ltd.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nostrum Laboratories Inc.
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Pack Pharmaceuticals
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescription Dispensing Service Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Va Cmop Dallas
Dosage forms
FormRouteStrength
CapsuleOral10 mg
CapsuleOral20 mg
SuppositoryRectal10 mg
SuppositoryRectal20 mg
CapsuleOral10 mg/1
CapsuleOral20 mg/1
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)198-200 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0019000000-0d247806d6203409cc16
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014j-0591000000-7d11d429795ac27fa093
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000t-0910000000-42d97ebe5da8190aa202
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001m-2900000000-32c34cd63ced296fee89
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kf-5900000000-1d4473d813b920140b81
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00lr-0009000000-9e65aa6e4b407ea80734
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000f-3984000000-e855ded4bfe08c600884
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-007c-3900000000-fb37337024398fe8044d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-006t-9600000000-db1bff24de3a9b89b68d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00r2-9200000000-22caea8b3219419be51f
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-01vk-6900000000-a75ce07d3bc58c9e773b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-5829000000-bfa87ed6f54b64fe3942
MS/MS Spectrum - , positiveLC-MS/MSsplash10-1000-1698000000-9bfc929b8cee2ec1d841
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dj-6911100000-64e355e5e08c884173b8

Taxonomy

Description
This 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).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Not Available
Direct Parent
Benzothiazines
Alternative Parents
Alpha amino acids and derivatives / Pyridines and derivatives / Organosulfonamides / 1,2-thiazines / Benzenoids / Imidolactams / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Carboximidic acids
show 6 more
Substituents
Alpha-amino acid or derivatives / Benzothiazine / Ortho-thiazine / Pyridine / Organosulfonic acid amide / Benzenoid / Imidolactam / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Heteroaromatic compound
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid amide, pyridines, benzothiazine (CHEBI:8249)

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...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
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 gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
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
Substrate
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. 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]
  2. Du H, Wei Z, Yan Y, Xiong Y, Zhang X, Shen L, Ruan Y, Wu X, Xu Q, He L, Qin S: Functional Characterization of Human CYP2C9 Allelic Variants in COS-7 Cells. Front Pharmacol. 2016 Apr 25;7:98. doi: 10.3389/fphar.2016.00098. eCollection 2016. [PubMed:27199745]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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 ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
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, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
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
Uniprot Name
Solute carrier family 22 member 11
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Drug created on June 13, 2005 07:24 / Updated on December 09, 2018 01:05