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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:43 UTC
HMDB IDHMDB0014473
Secondary Accession Numbers
  • HMDB14473
Metabolite Identification
Common NameIndomethacin
DescriptionIndomethacin, also known as aconip or indocin, belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group. Indomethacin is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, indomethacin is involved in indomethacin action pathway. Indomethacin is a potentially toxic compound. There have been reports of paresthesias, numbness, and convulsions. Its pharmacological effect is thought to be mediated through inhibition of the enzyme cyclooxygenase (COX), the enzyme responsible for catalyzes the rate-limiting step in prostaglandin synthesis via the arachidonic acid pathway. Indomethacin is a non-steroidal antiinflammatory agent (NSAIA) with antiinflammatory, analgesic and antipyretic activity.
Structure
Data?1582753183
Synonyms
ValueSource
1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acidChEBI
AconipChEBI
IndocinChEBI
IndometacinaChEBI
IndometacineChEBI
IndometacinumChEBI
{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acidChEBI
IndometacinKegg
1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetateGenerator
{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetateGenerator
IMNHMDB
IndometacynaHMDB
IndomethacineHMDB
IndomethacinumHMDB
IndomethancinHMDB
IndomethazineHMDB
IndomethineHMDB
IndometicinaHMDB
Hydrochloride, indomethacinHMDB
MetindolHMDB
OsmosinHMDB
AmunoHMDB
Indomet 140HMDB
Indomethacin hydrochlorideHMDB
IndocidHMDB
Chemical FormulaC19H16ClNO4
Average Molecular Weight357.788
Monoisotopic Molecular Weight357.076785712
IUPAC Name2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
Traditional Nameindomethacin
CAS Registry Number53-86-1
SMILES
COC1=CC2=C(C=C1)N(C(=O)C1=CC=C(Cl)C=C1)C(C)=C2CC(O)=O
InChI Identifier
InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)
InChI KeyCGIGDMFJXJATDK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassBenzoylindoles
Direct ParentBenzoylindoles
Alternative Parents
Substituents
  • Benzoylindole
  • Indole-3-acetic acid derivative
  • Indolecarboxylic acid derivative
  • Indolyl carboxylic acid derivative
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 3-alkylindole
  • Indole
  • Benzoic acid or derivatives
  • Anisole
  • Benzoyl
  • Chlorobenzene
  • Alkyl aryl ether
  • Halobenzene
  • Benzenoid
  • Substituted pyrrole
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Pyrrole
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0024 g/LNot Available
LogP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP4.25ALOGPS
logP3.53ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.81 m³·mol⁻¹ChemAxon
Polarizability36.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9100000000-2545b33ef519ca9557d7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9100000000-2545b33ef519ca9557d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0921000000-71472b2fb43c8acb2e55Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-4911000000-35eb3bff6897ef637c32Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-2902000000-8effecdaf737eb86e781Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0901000000-aa0cdbd9e10c432d837cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014u-2900000000-3bf048feb0cc9b0867e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0009000000-5a4abda1542473813a5dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0019000000-b80206e17a22fdf15299Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0093000000-4e04725a4a7ea8db1880Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0bt9-0906000000-44825d096b6f8c6091abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-053r-0890000000-e9f8e33084842b2a91e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-5aee2869a858e70aa8cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-5aee2869a858e70aa8cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0019000000-b9916635c4db449698abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0092000000-270cd44f32c881ded6aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-0973000000-6e9ac766080e35c8b297Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-053r-0790000000-b0e6139fc1746c17ddb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-1df95eb7ff5058a870ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0009000000-6a65e96ca253d6a3dda0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-08gi-0195000000-7ea82149ddaa783e01dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-1208c0d5e605b8b69605Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4r-0709000000-1814b324e15b59fa31a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0009000000-2429b2c6a858186ce401Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-93f3bd184f0f8af5030aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-2696000000-adec10da91c34dd6a1f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-c5d3ca4cfffc61e97844Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0039000000-108283a6771c753d8ab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dm-0394000000-eb1ba613d190aeacba7fSpectrum
MSMass Spectrum (Electron Ionization)splash10-000i-1901000000-710010c41f0ded9b0f17Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 DB00328 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00328 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00328
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00030512
Chemspider ID3584
KEGG Compound IDC01926
BioCyc IDCPD-10545
BiGG IDNot Available
Wikipedia LinkIndometacin
METLIN IDNot Available
PubChem Compound3715
PDB IDIMN
ChEBI ID49662
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lum GM, Aisenbrey GA, Dunn MJ, Berl T, Schrier RW, McDonald KM: In vivo effect of indomethacin to potentiate the renal medullary cyclic AMP response to vasopressin. J Clin Invest. 1977 Jan;59(1):8-13. [PubMed:187624 ]
  2. Ragheb M: The clinical significance of lithium-nonsteroidal anti-inflammatory drug interactions. J Clin Psychopharmacol. 1990 Oct;10(5):350-4. [PubMed:2258452 ]
  3. Akbarpour F, Afrasiabi A, Vaziri ND: Severe hyperkalemia caused by indomethacin and potassium supplementation. South Med J. 1985 Jun;78(6):756-7. [PubMed:4002013 ]
  4. HART FD, BOARDMAN PL: INDOMETHACIN: A NEW NON-STEROID ANTI-INFLAMMATORY AGENT. Br Med J. 1963 Oct 19;2(5363):965-70. [PubMed:14056924 ]
  5. Phelan KM, Mosholder AD, Lu S: Lithium interaction with the cyclooxygenase 2 inhibitors rofecoxib and celecoxib and other nonsteroidal anti-inflammatory drugs. J Clin Psychiatry. 2003 Nov;64(11):1328-34. [PubMed:14658947 ]