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Identification
NameEtodolac
Accession NumberDB00749  (APRD00067)
TypeSmall Molecule
GroupsApproved, Investigational, Vet Approved
Description

Etodolac is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic and antipyretic properties. Its therapeutic effects are due to its ability to inhibit prostaglandin synthesis. It is indicated for relief of signs and symptoms of rheumatoid arthritis and osteoarthritis.

Structure
Thumb
Synonyms
(+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid
(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid
1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acid
1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid
1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetic acid
Étodolac
Etodolac
Etodolaco
Etodolacum
Etodolic acid
Etodolsäure
External Identifiers
  • AY 24236
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Etodolaccapsule200 mgoralAa Pharma Inc1997-08-21Not applicableCanada
Etodolaccapsule300 mgoralAa Pharma Inc1997-08-21Not applicableCanada
Gen-etodolac 200mgcapsule200 mgoralGenpharm Ulc1999-01-122009-08-05Canada
Gen-etodolac 300mgcapsule300 mgoralGenpharm Ulc1999-01-122009-08-05Canada
Novo-etodolac 200 mgcapsule200 mgoralNovopharm LimitedNot applicableNot applicableCanada
Novo-etodolac 300 mgcapsule300 mgoralNovopharm LimitedNot applicableNot applicableCanada
Nu-etodolaccapsule300 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-etodolaccapsule200 mgoralNu Pharm IncNot applicableNot applicableCanada
Taro-etodolaccapsule300 mgoralTaro Pharmaceuticals Inc2000-10-20Not applicableCanada
Taro-etodolac 200 mgcapsule200 mgoralTaro Pharmaceuticals Inc2000-10-20Not applicableCanada
Ultradol - Cap 200mgcapsule200 mgoralProcter & Gamble Pharmaceuticals Canada Inc1995-12-312002-07-23Canada
Ultradol - Cap 300mgcapsule300 mgoralProcter & Gamble Pharmaceuticals Canada Inc1995-12-312008-09-09Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Etodolactablet, film coated400 mg/1oralPhysicians Total Care, Inc.2000-01-172016-04-05Us
Etodolaccapsule300 mg/1oralREMEDYREPACK INC.2011-06-272016-04-05Us
Etodolactablet, film coated400 mg/1oralTaro Pharmaceuticals U.S.A., Inc.1998-03-112016-04-05Us
Etodolactablet, film coated400 mg/1oralPd Rx Pharmaceuticals, Inc.1998-05-202016-04-05Us
Etodolactablet, film coated, extended release600 mg/1oralGolden State Medical Supply, Inc.2003-03-132016-04-05Us
Etodolactablet, film coated400 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-192016-04-05Us
Etodolactablet, film coated500 mg/1oralAidarex Pharmaceuticals LLC2009-09-092016-04-05Us
Etodolactablet, film coated500 mg/1oralClinical Solutions Wholesale2009-09-092016-04-05Us
Etodolactablet, film coated, extended release600 mg/1oralCadila Healthcare Limited2014-02-152016-04-05Us
Etodolactablet, film coated500 mg/1oralPhysicians Total Care, Inc.1999-04-212016-04-05Us
Etodolaccapsule300 mg/1oralANI Pharmaceuticals, Inc.2015-02-012016-04-05Us
Etodolaccapsule200 mg/1oralApotex Corp.2003-05-012016-04-05Us
Etodolactablet, film coated400 mg/1oralPreferred Pharmaceuticals Inc.2015-08-182016-04-05Us
Etodolactablet, film coated, extended release400 mg/1oralDispensing Solutions, Inc.2001-02-092016-04-05Us
Etodolactablet, film coated400 mg/1oralAidarex Pharmaceuticals LLC1998-05-202016-04-05Us
Etodolactablet, coated400 mg/1oralEon Labs, Inc.1997-04-112017-12-31Us
Etodolactablet, film coated400 mg/1oralTeva Pharmaceuticals USA Inc1998-05-202016-04-23Us
Etodolactablet400 mg/1oralREMEDYREPACK INC.2010-10-012016-04-05Us
Etodolaccapsule300 mg/1oralTaro Pharmaceuticals U.S.A., Inc.1998-04-302016-04-05Us
Etodolactablet, film coated400 mg/1oralSTAT Rx USA LLC2003-05-012016-04-05Us
Etodolactablet, film coated, extended release500 mg/1oralGolden State Medical Supply, Inc.2003-03-132016-04-05Us
Etodolactablet, film coated500 mg/1oralLake Erie Medical DBA Quality Care Products LLC2000-04-252016-04-05Us
Etodolactablet, film coated, extended release500 mg/1oralCadila Healthcare Limited2014-02-152016-04-05Us
Etodolaccapsule200 mg/1oralANI Pharmaceuticals, Inc.2015-03-092016-04-05Us
Etodolactablet, film coated, extended release600 mg/1oralZydus Pharmaceuticals (USA) Inc.2014-02-152016-04-05Us
Etodolactablet, film coated400 mg/1oralRebel Distributors Corp1998-03-112016-04-05Us
Etodolactablet, coated500 mg/1oralEon Labs, Inc.1999-04-192017-12-31Us
Etodolactablet, film coated, extended release400 mg/1oralPhysicians Total Care, Inc.2005-01-202016-04-05Us
Etodolactablet, film coated, extended release400 mg/1oralCadila Healthcare Limited2014-02-152016-04-05Us
Etodolactablet500 mg/1oralDIRECT RX2014-01-012016-04-05Us
Etodolactablet, film coated, extended release500 mg/1oralZydus Pharmaceuticals (USA) Inc.2014-02-152016-04-05Us
Etodolaccapsule, gelatin coated300 mg/1oralRebel Distributors Corp1999-09-162016-04-05Us
Etodolaccapsule200 mg/1oralKAISER FOUNDATION HOSPITALS2005-12-012016-04-23Us
Etodolactablet, film coated, extended release500 mg/1oralPhysicians Total Care, Inc.2005-01-202016-04-05Us
Etodolaccapsule300 mg/1oralREMEDYREPACK INC.2010-10-062016-04-05Us
Etodolaccapsule200 mg/1oralTaro Pharmaceuticals U.S.A., Inc.1998-04-302016-04-05Us
Etodolaccapsule300 mg/1oralRebel Distributors Corp2010-03-312016-04-05Us
Etodolactablet, film coated, extended release400 mg/1oralGolden State Medical Supply, Inc.2003-03-132016-04-05Us
Etodolaccapsule300 mg/1oralPd Rx Pharmaceuticals, Inc.1998-04-302016-04-05Us
Etodolaccapsule300 mg/1oralSTAT Rx USA LLC1998-04-302016-04-05Us
Etodolactablet, film coated400 mg/1oralKAISER FOUNDATION HOSPITALS2015-01-132016-04-23Us
Etodolactablet, film coated400 mg/1oralH.J. Harkins Company, Inc.1998-05-202016-04-05Us
Etodolaccapsule200 mg/1oralAphena Pharma Solutions Tennessee, Llc1998-04-052016-04-05Us
Etodolaccapsule300 mg/1oralNorthwind Pharmaceuticals, LLC2014-11-132016-04-05Us
Etodolactablet, film coated400 mg/1oralRebel Distributors Corp2010-04-302016-04-05Us
Etodolactablet, film coated500 mg/1oralGolden State Medical Supply, Inc.1998-03-122016-04-05Us
Etodolactablet, coated500 mg/1oralPd Rx Pharmaceuticals, Inc.1999-04-192016-04-05Us
Etodolactablet, extended release400 mg/1oralbryant ranch prepack2003-03-132016-04-05Us
Etodolactablet, film coated400 mg/1oralDIRECT RX2014-01-012016-04-05Us
Etodolactablet, coated400 mg/1oralAmerican Health Packaging2016-02-012016-04-05Us
Etodolactablet, film coated, extended release400 mg/1oralZydus Pharmaceuticals (USA) Inc.2014-02-152016-04-05Us
Etodolactablet400 mg/1oralSTAT Rx USA LLC1998-03-112016-04-05Us
Etodolactablet, film coated, extended release500 mg/1oralTeva Pharmaceuticals USA Inc2000-08-112016-04-23Us
Etodolactablet, extended release600 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2003-03-132016-04-05Us
Etodolaccapsule300 mg/1oralAphena Pharma Solutions Tennessee, Llc1998-04-052016-04-05Us
Etodolactablet500 mg/1oralNorthwind Pharmaceuticals, LLC2014-10-292016-04-05Us
Etodolactablet, film coated400 mg/1oralLake Erie Medical DBA Quality Care Products LLC1998-05-202016-04-05Us
Etodolactablet, film coated400 mg/1oralGolden State Medical Supply, Inc.1998-03-112016-04-05Us
Etodolactablet, coated400 mg/1oralPd Rx Pharmaceuticals, Inc.1997-04-112016-04-05Us
Etodolactablet, film coated, extended release500 mg/1oralbryant ranch prepack2010-12-302016-04-05Us
Etodolactablet, film coated400 mg/1oralREMEDYREPACK INC.2015-10-272016-04-05Us
Etodolactablet, coated500 mg/1oralPreferred Pharmaceuticals, Inc.2015-04-202016-04-05Us
Etodolactablet, film coated, extended release400 mg/1oralCarilion Materials Management2001-02-092016-04-05Us
Etodolactablet, extended release500 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2003-03-132016-04-05Us
Etodolactablet, film coated400 mg/1oralAphena Pharma Solutions Tennessee, Llc1998-03-112016-04-05Us
Etodolactablet, film coated, extended release500 mg/1oralUnit Dose Services2010-12-302016-04-05Us
Etodolactablet, film coated400 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC1998-03-112016-04-05Us
Etodolaccapsule300 mg/1oralGolden State Medical Supply, Inc.1998-04-052016-04-05Us
Etodolaccapsule200 mg/1oralPhysicians Total Care, Inc.2005-04-272016-04-05Us
Etodolactablet, film coated500 mg/1oralbryant ranch prepack1999-04-212016-04-05Us
Etodolactablet, film coated500 mg/1oralApotex Corp.2003-05-012016-04-05Us
Etodolaccapsule300 mg/1oralPreferred Pharmaceuticals, Inc2012-01-172016-04-05Us
Etodolactablet, coated400 mg/1oralAmerican Health Packaging2014-09-222016-03-31Us
Etodolactablet, film coated400 mg/1oralBlenheim Pharmacal, Inc.2013-10-082016-04-05Us
Etodolactablet, film coated500 mg/1oralTeva Pharmaceuticals USA Inc2009-09-092016-04-23Us
Etodolactablet, extended release400 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2003-03-132016-04-05Us
Etodolactablet, film coated500 mg/1oralAphena Pharma Solutions Tennessee, Llc1998-03-122016-04-05Us
Etodolaccapsule300 mg/1oralUnit Dose Services1998-04-302016-04-05Us
Etodolaccapsule300 mg/1oralLake Erie Medical & Surgical Supply DBA Qualtiy Care Products LLC2012-03-062016-04-05Us
Etodolaccapsule200 mg/1oralGolden State Medical Supply, Inc.1998-04-052016-04-05Us
Etodolactablet, film coated, extended release600 mg/1oralPhysicians Total Care, Inc.2011-09-132016-04-05Us
Etodolactablet, film coated400 mg/1oralbryant ranch prepack2010-04-302016-04-05Us
Etodolactablet, film coated400 mg/1oralApotex Corp.2003-05-012016-04-05Us
Etodolactablet, film coated400 mg/1oralPreferred Pharmaceuticals, Inc2012-01-172016-04-05Us
Etodolactablet, film coated400 mg/1oralRed Pharm Drug Inc.2008-12-012016-04-05Us
Etodolactablet, coated500 mg/1oralEon Labs, Inc.2015-04-202016-04-23Us
Etodolactablet, film coated, extended release400 mg/1oralTeva Pharmaceuticals USA Inc2001-02-092016-04-23Us
Etodolactablet, film coated500 mg/1oralTaro Pharmaceuticals U.S.A., Inc.2000-04-252016-04-05Us
Etodolactablet, film coated400 mg/1oralPd Rx Pharmaceuticals, Inc.2003-05-012016-04-05Us
Etodolactablet, film coated400 mg/1oralUnit Dose Services1998-03-112016-04-05Us
Etodolactablet, extended release500 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-062016-04-05Us
Etodolactablet, film coated400 mg/1oralClinical Solutions Wholesale1998-03-112016-04-05Us
Etodolaccapsule300 mg/1oralPhysicians Total Care, Inc.2010-03-312016-04-05Us
Etodolaccapsule300 mg/1oralApotex Corp.2003-05-012016-04-05Us
Etodolactablet, film coated400 mg/1oralPreferred Pharmaceuticals, Inc.2012-01-182016-04-05Us
Etodolactablet, film coated400 mg/1oralDispensing Solutions, Inc.1998-05-202016-04-05Us
Etodolactablet, coated400 mg/1oralEon Labs, Inc.2015-04-202016-04-23Us
Etodolactablet, film coated, extended release600 mg/1oralTeva Pharmaceuticals USA Inc2000-08-172016-04-23Us
Lodinecapsule, gelatin coated300 mg/1oralbryant ranch prepack2009-06-302016-04-05Us
Over the Counter ProductsNot Available
International Brands
NameCompany
BodopineYuan Chou
DolaritDrogsan
DolchisKorea United Pharm
DolocUnifarma
DualganITF
EccoxolacMeda
Edolar FortPfizer
EdopainIncepta
Edopain ERIncepta
ElacRoyal
ElderinLek
EricU.C. Pharma
EsodaxMünir Sahin
ETLSenton
EtodinNobel
Etodin FortUlkar
EtodolYuhan
EtodonShinlon
EtoflamStandard Chem
Etol FortNobel
EtolacAlkaloid
EtomaxIpca
Etomax-ERIpca
EtonoxCharoen Bhaesaj
EtopanWinthrop Pharmaceuticals
EtopinU-Liang
Lodine XLWyeth
Brand mixturesNot Available
SaltsNot Available
Categories
UNII2M36281008
CAS number41340-25-4
WeightAverage: 287.3535
Monoisotopic: 287.152143543
Chemical FormulaC17H21NO3
InChI KeyInChIKey=NNYBQONXHNTVIJ-UHFFFAOYSA-N
InChI
InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)
IUPAC Name
2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
SMILES
CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Indole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor acute and long-term management of signs and symptoms of osteoarthritis and rheumatoid arthritis, as well as for the management of pain.
PharmacodynamicsEtodolac is an anti-inflammatory agent with analgesic and antipyretic properties. It is used to treat osteoarthritis, rheumatoid arthritis and control acute pain. The therapeutic effects of etodolac are achieved via inhibition of the synthesis of prostaglandins involved in fever, pain, swelling and inflammation. Etodolac is administered as a racemate. As with other NSAIDs, the S-form has been shown to be active while the R-form is inactive. Both enantiomers are stable and there is no evidence of R- to S- conversion in vivo.
Mechanism of actionSimilar to other NSAIDs, the anti-inflammatory effects of etodolac result from inhibition of the enzyme cycooxygenase (COX). This decreases the synthesis of peripheral prostaglandins involved in mediating inflammation. Etodolac binds to the upper portion of the COX enzyme active site and prevents its substrate, arachidonic acid, from entering the active site. Etodolac was previously thought to be a non-selective COX inhibitor, but it is now known to be 5 – 50 times more selective for COX-2 than COX-1. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.
Related Articles
AbsorptionBased on mass balance studies, the systemic bioavailability of etodolac from either the tablet or capsule formulation is at least 80%.
Volume of distribution
  • 390 mL/kg
Protein binding> 99% bound, primarily to albumin
Metabolism

Etodolac is extensively metabolized in the liver. Renal elimination of etodolac and its metabolites is the primary route of excretion (72%). Metabolites found in urine (with percents of the administered dose) are: unchanged etodolac (1%), etodolac glucuronide (13%), hydroxylated metabolites (6-, 7-, and 8-OH; 5%), hydroxylated metabolite glucuronides (20%), and unidentified metabolites (33%). Fecal excretion accounts for 16% of its elimination.

SubstrateEnzymesProduct
Etodolac
6-HydroxyetodolacDetails
Etodolac
7-HydroxyetodolacDetails
Etodolac
Etodolac acyl glucuronideDetails
Route of eliminationIt is not known whether etodolac is excreted in human milk; however, based on its physical-chemical properties, excretion into breast milk is expected. Etodolac is extensively metabolized in the liver. The hydroxylated-etodolac metabolites undergo further glucuronidation followed by renal excretion and partial elimination in the feces (16% of dose). Approximately 1% of a etodolac dose is excreted unchanged in the urine with 72% of the dose excreted into urine as parent drug plus metabolite.
Half lifeTerminal t1/2, 7.3 ± 4.0 hours. Distribution t1/2, 0.71 ± 0.50 hours
Clearance
  • Oral cl=49.1 mL/h/kg [Normal healthy adults]
  • Oral cl=49.4 mL/h/kg [Healthy males (18-65 years)]
  • Oral cl=35.7 mL/h/kg [Healthy females (27-65 years)]
  • Oral cl=45.7 mL/h/kg [Eldery (>65 years)]
  • Oral cl=58.3 mL/h/kg [Renal impairement (46-73 years)]
  • Oral cl=42.0 mL/h/kg [Hepatic impairement (34-60 years)]
ToxicitySelective COX-2 inhibitors have been associated with increased risk of serious cardiovascular events (e.g. myocardial infarction, stroke) in some patients. Current data is insufficient to assess the cardiovascular risk of etodolac. Etodolac may increase blood pressure and/or cause fluid retention and edema. Risk of GI toxicity including bleeding, ulceration and perforation. Risk of direct renal injury, including renal papillary necrosis. Anaphylactoid and serious skin reactions (e.g. exfoliative dermatitis, Stevens-Johnson syndrome, toxic epidermal necrolysis) have been reported. Common adverse events include abdominal pain, constipation, diarrhea, dyspepsia, flatulence, GI bleeding, GI perforation, nausea, peptic ulcer, vomiting, renal function abnormalities, anemia, dizziness, edema, liver function test abnormalities, headache, prolonged bleeding time, pruritus, rash, tinnitus. Symptoms of overdose include lethargy, drowsiness, nausea, vomiting, and epigastric pain.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Etodolac Action PathwayDrug actionSMP00084
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.9065
Caco-2 permeable+0.5726
P-glycoprotein substrateSubstrate0.7462
P-glycoprotein inhibitor INon-inhibitor0.9242
P-glycoprotein inhibitor IINon-inhibitor0.8988
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8545
CYP450 2D6 substrateNon-substrate0.7567
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6904
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9453
BiodegradationNot ready biodegradable0.9835
Rat acute toxicity3.4536 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9808
hERG inhibition (predictor II)Non-inhibitor0.7763
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Aaipharma llc
  • Apotex inc
  • Endo pharmaceuticals inc
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Taro pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Wyeth pharmaceuticals inc
  • Point holdings inc
  • Watson laboratories inc florida
  • Actavis elizabeth llc
  • Apotex inc etobicoke site
  • Mylan laboratories inc
  • Ranbaxy laboratories ltd
Packagers
Dosage forms
FormRouteStrength
Capsuleoral200 mg/1
Capsuleoral200 mg
Capsuleoral300 mg/1
Capsuleoral300 mg
Capsule, gelatin coatedoral300 mg/1
Tabletoral400 mg/1
Tabletoral500 mg/1
Tablet, coatedoral400 mg/1
Tablet, coatedoral500 mg/1
Tablet, extended releaseoral400 mg/1
Tablet, extended releaseoral500 mg/1
Tablet, extended releaseoral600 mg/1
Tablet, film coatedoral400 mg/1
Tablet, film coatedoral500 mg/1
Tablet, film coated, extended releaseoral400 mg/1
Tablet, film coated, extended releaseoral500 mg/1
Tablet, film coated, extended releaseoral600 mg/1
Prices
Unit descriptionCostUnit
Etodolac CR 600 mg 24 Hour tablet2.76USD tablet
Lodine 400 mg tablet2.65USD tablet
Lodine 500 mg tablet1.8USD tablet
Etodolac CR 500 mg 24 Hour tablet1.6USD tablet
Etodolac 500 mg tablet1.52USD tablet
Etodolac 400 mg tablet1.5USD tablet
Etodolac CR 400 mg 24 Hour tablet1.46USD tablet
Etodolac 300 mg capsule1.31USD capsule
Apo-Etodolac 200 mg Capsule0.8USD capsule
Apo-Etodolac 300 mg Capsule0.8USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point146.5 °CPhysProp
water solubility16 mg/LNot Available
logP2.5Not Available
pKa4.65Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0392 mg/mLALOGPS
logP3.39ALOGPS
logP3.44ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.16 m3·mol-1ChemAxon
Polarizability31.94 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

Christopher A. Demerson, Leslie G. Humber, “Process for preparing 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)-indole-1-acetic acid, etodolac.” U.S. Patent US4585877, issued May, 1977.

US4585877
General ReferencesNot Available
External Links
ATC CodesM01AB08
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelDownload (290 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabEtodolac may increase the anticoagulant activities of Abciximab.
AcenocoumarolEtodolac may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Etodolac is combined with Acetylsalicylic acid.
AliskirenEtodolac may decrease the antihypertensive activities of Aliskiren.
AlteplaseEtodolac may increase the anticoagulant activities of Alteplase.
AmikacinEtodolac 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 Etodolac.
AnistreplaseEtodolac may increase the anticoagulant activities of Anistreplase.
ApixabanThe risk or severity of adverse effects can be increased when Etodolac is combined with Apixaban.
ArbekacinEtodolac may decrease the excretion rate of Arbekacin which could result in a lower serum level and potentially a reduction in efficacy.
BalsalazideEtodolac may increase the nephrotoxic activities of Balsalazide.
Citric AcidEtodolac may increase the anticoagulant activities of Citric Acid.
ColesevelamColesevelam can cause a decrease in the absorption of Etodolac resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Etodolac is combined with Collagenase.
CyclosporineEtodolac may increase the nephrotoxic activities of Cyclosporine.
Dabigatran etexilateEtodolac may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinEtodolac may increase the anticoagulant activities of Dalteparin.
DasatinibDasatinib may increase the anticoagulant activities of Etodolac.
DeferasiroxThe risk or severity of adverse effects can be increased when Etodolac is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Etodolac is combined with Deoxycholic Acid.
DesmopressinThe risk or severity of adverse effects can be increased when Etodolac is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Etodolac.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Etodolac.
DicoumarolEtodolac may increase the anticoagulant activities of Dicoumarol.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Etodolac.
DrospirenoneEtodolac may increase the hyperkalemic activities of Drospirenone.
Edetic AcidEtodolac may increase the anticoagulant activities of Edetic Acid.
EnoxaparinEtodolac may increase the anticoagulant activities of Enoxaparin.
EplerenoneEtodolac may decrease the antihypertensive activities of Eplerenone.
Ethyl biscoumacetateEtodolac may increase the anticoagulant activities of Ethyl biscoumacetate.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Etodolac.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Etodolac.
Fondaparinux sodiumEtodolac may increase the anticoagulant activities of Fondaparinux sodium.
FramycetinEtodolac may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
GentamicinEtodolac 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 Etodolac.
HaloperidolThe risk or severity of adverse effects can be increased when Etodolac is combined with Haloperidol.
HeparinEtodolac may increase the anticoagulant activities of Heparin.
HomoharringtonineThe risk or severity of adverse effects can be increased when Etodolac is combined with Homoharringtonine.
HydralazineEtodolac may decrease the antihypertensive activities of Hydralazine.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Etodolac is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Etodolac.
IcosapentThe risk or severity of adverse effects can be increased when Etodolac is combined with Icosapent.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Etodolac.
KanamycinEtodolac 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 Etodolac.
LimaprostLimaprost may increase the antiplatelet activities of Etodolac.
LithiumThe serum concentration of Lithium can be increased when it is combined with Etodolac.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Etodolac.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Etodolac.
NadololEtodolac may decrease the antihypertensive activities of Nadolol.
NeomycinEtodolac may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NetilmicinEtodolac 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 Etodolac is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Etodolac.
PamidronateThe risk or severity of adverse effects can be increased when Etodolac is combined with Pamidronate.
ParoxetineParoxetine may increase the antiplatelet activities of Etodolac.
PemetrexedThe serum concentration of Pemetrexed can be increased when it is combined with Etodolac.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Etodolac.
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Etodolac.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Etodolac.
PhenindioneEtodolac may increase the anticoagulant activities of Phenindione.
PhenprocoumonEtodolac may increase the anticoagulant activities of Phenprocoumon.
PorfimerEtodolac may increase the photosensitizing activities of Porfimer.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Etodolac.
ProbenecidThe serum concentration of Etodolac can be increased when it is combined with Probenecid.
ReteplaseEtodolac may increase the anticoagulant activities of Reteplase.
RibostamycinEtodolac may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RidogrelEtodolac may increase the anticoagulant activities of Ridogrel.
RivaroxabanEtodolac may increase the anticoagulant activities of Rivaroxaban.
SparfloxacinEtodolac may increase the neuroexcitatory activities of Sparfloxacin.
SpectinomycinEtodolac may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptokinaseEtodolac may increase the anticoagulant activities of Streptokinase.
StreptomycinEtodolac may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
SulodexideEtodolac may increase the anticoagulant activities of Sulodexide.
TacrolimusEtodolac may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Etodolac.
TenecteplaseEtodolac may increase the anticoagulant activities of Tenecteplase.
TenofovirThe risk or severity of adverse effects can be increased when Etodolac is combined with Tenofovir.
TipranavirTipranavir may increase the antiplatelet activities of Etodolac.
TobramycinEtodolac may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideEtodolac may decrease the diuretic activities of Torasemide.
TositumomabThe risk or severity of adverse effects can be increased when Etodolac is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Etodolac.
TriamtereneEtodolac may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Etodolac.
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Etodolac.
UrokinaseEtodolac may increase the anticoagulant activities of Urokinase.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Etodolac.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Etodolac.
VenlafaxineVenlafaxine may increase the antiplatelet activities of Etodolac.
VerteporfinEtodolac may increase the photosensitizing activities of Verteporfin.
Vitamin EVitamin E may increase the antiplatelet activities of Etodolac.
WarfarinEtodolac may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Avoid alcohol.
  • Food increases the peak plasma concentration of extended-release tablets with no effect on extent of absorption.
  • Food increases the time to peak concentration of regular release oral formulations by 1.4 to 3.8 hours with no effect on extent of absorption.
  • Take with food to reduce gastric irritation.

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. Chen WS, Liu JH, Wei SJ, Liu JM, Hong CY, Yang WK: Colon cancer cells with high invasive potential are susceptible to induction of apoptosis by a selective COX-2 inhibitor. Cancer Sci. 2003 Mar;94(3):253-8. [PubMed:12824918 ]
  2. Chen WS, Wei SJ, Liu JM, Hsiao M, Kou-Lin J, Yang WK: Tumor invasiveness and liver metastasis of colon cancer cells correlated with cyclooxygenase-2 (COX-2) expression and inhibited by a COX-2-selective inhibitor, etodolac. Int J Cancer. 2001 Mar 15;91(6):894-9. [PubMed:11275997 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Kusuhara H, Komatsu H, Sumichika H, Sugahara K: Reactive oxygen species are involved in the apoptosis induced by nonsteroidal anti-inflammatory drugs in cultured gastric cells. Eur J Pharmacol. 1999 Nov 3;383(3):331-7. [PubMed:10594327 ]
  5. Svendsen KB, Bech JN, Sorensen TB, Pedersen EB: A comparison of the effects of etodolac and ibuprofen on renal haemodynamics, tubular function, renin, vasopressin and urinary excretion of albumin and alpha-glutathione-S-transferase in healthy subjects: a placebo-controlled cross-over study. Eur J Clin Pharmacol. 2000 Aug;56(5):383-8. [PubMed:11009046 ]
  6. Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222 ]
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. Campbell NB, Jones SL, Blikslager AT: The effects of cyclo-oxygenase inhibitors on bile-injured and normal equine colon. Equine Vet J. 2002 Jul;34(5):493-8. [PubMed:12358053 ]
  2. Glaser K, Sung ML, O'Neill K, Belfast M, Hartman D, Carlson R, Kreft A, Kubrak D, Hsiao CL, Weichman B: Etodolac selectively inhibits human prostaglandin G/H synthase 2 (PGHS-2) versus human PGHS-1. Eur J Pharmacol. 1995 Jul 25;281(1):107-11. [PubMed:8566109 ]
  3. Hirate K, Uchida A, Ogawa Y, Arai T, Yoda K: Zaltoprofen, a non-steroidal anti-inflammatory drug, inhibits bradykinin-induced pain responses without blocking bradykinin receptors. Neurosci Res. 2006 Apr;54(4):288-94. Epub 2006 Feb 13. [PubMed:16473424 ]
  4. Riendeau D, Percival MD, Boyce S, Brideau C, Charleson S, Cromlish W, Ethier D, Evans J, Falgueyret JP, Ford-Hutchinson AW, Gordon R, Greig G, Gresser M, Guay J, Kargman S, Leger S, Mancini JA, O'Neill G, Ouellet M, Rodger IW, Therien M, Wang Z, Webb JK, Wong E, Chan CC, et al.: Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. Br J Pharmacol. 1997 May;121(1):105-17. [PubMed:9146894 ]
  5. Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXR...
Gene Name:
RXRA
Uniprot ID:
P19793
Molecular Weight:
50810.835 Da
References
  1. Kolluri SK, Corr M, James SY, Bernasconi M, Lu D, Liu W, Cottam HB, Leoni LM, Carson DA, Zhang XK: The R-enantiomer of the nonsteroidal antiinflammatory drug etodolac binds retinoid X receptor and induces tumor-selective apoptosis. Proc Natl Acad Sci U S A. 2005 Feb 15;102(7):2525-30. Epub 2005 Feb 7. [PubMed:15699354 ]

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. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular Weight:
59940.495 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular Weight:
60337.835 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein kinase c binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Molecular Weight:
59809.075 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 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 ]

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. Mignot I, Presle N, Lapicque F, Monot C, Dropsy R, Netter P: Albumin binding sites for etodolac enantiomers. Chirality. 1996;8(3):271-80. [PubMed:8777148 ]
  2. Muller N, Lapicque F, Monot C, Payan E, Dropsy R, Netter P: Stereoselective binding of etodolac to human serum albumin. Chirality. 1992;4(4):240-6. [PubMed:1389961 ]
  3. Smith PC, Song WQ, Rodriguez RJ: Covalent binding of etodolac acyl glucuronide to albumin in vitro. Drug Metab Dispos. 1992 Nov-Dec;20(6):962-5. [PubMed:1362954 ]

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