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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:31 UTC
HMDB IDHMDB0014887
Secondary Accession Numbers
  • HMDB14887
Metabolite Identification
Common NameEtodolac
DescriptionEtodolac is only found in individuals that have used or taken this drug. It 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. Similar 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.
Structure
Data?1582753231
Synonyms
ValueSource
(+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acidChEBI
(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acidChEBI
1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acidChEBI
1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acidChEBI
1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetic acidChEBI
EtodolacoChEBI
EtodolacumChEBI
ETODOLIC ACIDChEBI
LodineKegg
(+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetateGenerator
(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetateGenerator
1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetateGenerator
1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetateGenerator
1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetateGenerator
ETODOLateGenerator
Etodolac, (-)-isomerHMDB
Etodolac, monosodium saltHMDB
Etodolac, (+-)-isomerHMDB
Etodolac, monosodium salt, (S)-isomerHMDB
Etodolac, monosodium salt, (+-) isomerHMDB
UltradolHMDB
Acid, etodolicHMDB
Etodolac, (S)-isomerHMDB
RamodarHMDB
Chemical FormulaC17H21NO3
Average Molecular Weight287.3535
Monoisotopic Molecular Weight287.152143543
IUPAC Name2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
Traditional Nameetodolac
CAS Registry Number41340-25-4
SMILES
CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC=C1
InChI Identifier
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)
InChI KeyNNYBQONXHNTVIJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives 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
  • 3-alkylindole
  • Indole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 - 148 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.039 g/LNot Available
LogP2.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.16 m³·mol⁻¹ChemAxon
Polarizability31.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-5690000000-7138dacb1eaaf2cdf09bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9178000000-933928ecb8877343883cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-3962000000-2dfafa7266e72ac813b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000l-0090000000-cb5392bab35da402835eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-66382e8a032519cc0610Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0090000000-1ab9e4ff7d60e90eca2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0290000000-308131d28773ab2c9701Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03dj-0890000000-ba74bd4789a5df9d1095Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-01pk-0920000000-3003d9d94ce99518b55eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0090000000-1644ab62d0cb24cc769eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000f-0090000000-0d0a55600dd433d684b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01ox-0090000000-17b2c48a871d73f3071aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0290000000-fe771b5ef7a99c3f79ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03dj-0980000000-50aec638935d673b713eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0910000000-ca92c4a042f65a5a6c9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0920000000-22f891e69de842afb76fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0910000000-3903a65f3f64f26aa9b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006x-0900000000-5bb09419198c9ca084c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0900000000-61c0ea8a828fd0570b07Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0900000000-4bec68aee4ff03d6d386Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dr-0890000000-e286df97fed2602fd759Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0090000000-39c676afa45ed8a7e018Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009f-0490000000-51e44ee3189b0f50c173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1900000000-6dd7415f505d8fdf0796Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0090000000-8e401f59407e86d7026aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01tl-0090000000-76de8abd58830a4798deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r03-0950000000-379fd5765e047bf96bfbSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00749 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00749 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00749
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3192
KEGG Compound IDC06991
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtodolac
METLIN IDNot Available
PubChem Compound3308
PDB IDNot Available
ChEBI ID4909
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available