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Record Information
Version5.0
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. In humans, indomethacin is involved in the indomethacin action pathway. Indomethacin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Indomethacin.
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0024 g/LNot Available
LogP3.4Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+Baker183.54830932474
DeepCCS[M+H]+CBM179.530932474
AllCCS[M+H]+Not Available181.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000997
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP10(4.25) g/LALOGPS
logP10(3.53) g/LChemAxon
logS10(-5.2) g/LALOGPS
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
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indomethacin,1TMS,#1COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=C(C)N2C(=O)C1=CC=C(Cl)C=C12966.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Indomethacin,1TBDMS,#1COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C(C)N2C(=O)C1=CC=C(Cl)C=C13205.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Indomethacin EI-B (Non-derivatized)splash10-002f-9100000000-2545b33ef519ca9557d72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indomethacin EI-B (Non-derivatized)splash10-002f-9100000000-2545b33ef519ca9557d72018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indomethacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0921000000-71472b2fb43c8acb2e552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indomethacin GC-MS (1 TMS) - 70eV, Positivesplash10-000i-4911000000-35eb3bff6897ef637c322017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indomethacin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-1901000000-710010c41f0ded9b0f172014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-qTof , Positive-QTOFsplash10-000i-2902000000-8effecdaf737eb86e7812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-qTof , Positive-QTOFsplash10-000i-0901000000-aa0cdbd9e10c432d837c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-qTof , Positive-QTOFsplash10-014u-2900000000-3bf048feb0cc9b0867e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-03di-0009000000-5a4abda1542473813a5d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-03di-0019000000-b80206e17a22fdf152992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-0002-0093000000-4e04725a4a7ea8db18802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-0bt9-0906000000-44825d096b6f8c6091ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-053r-0890000000-e9f8e33084842b2a91e02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-5aee2869a858e70aa8cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-5aee2869a858e70aa8cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-03di-0019000000-b9916635c4db449698ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-0002-0092000000-270cd44f32c881ded6aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-0a4j-0973000000-6e9ac766080e35c8b2972017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-053r-0790000000-b0e6139fc1746c17ddb72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-1df95eb7ff5058a870cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , negative-QTOFsplash10-03di-0009000000-6a65e96ca253d6a3dda02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-QFT , negative-QTOFsplash10-08gi-0195000000-7ea82149ddaa783e01df2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , positive-QTOFsplash10-00di-0900000000-1208c0d5e605b8b696052017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indomethacin LC-ESI-ITFT , positive-QTOFsplash10-0a4r-0709000000-1814b324e15b59fa31a52017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indomethacin 10V, Positive-QTOFsplash10-0a4l-0009000000-2429b2c6a858186ce4012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indomethacin 20V, Positive-QTOFsplash10-03di-0009000000-93f3bd184f0f8af5030a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indomethacin 40V, Positive-QTOFsplash10-03e9-2696000000-adec10da91c34dd6a1f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indomethacin 10V, Negative-QTOFsplash10-0a4i-0009000000-c5d3ca4cfffc61e978442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indomethacin 20V, Negative-QTOFsplash10-0bt9-0039000000-108283a6771c753d8ab82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indomethacin 40V, Negative-QTOFsplash10-03dm-0394000000-eb1ba613d190aeacba7f2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00328 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ragheb M: The clinical significance of lithium-nonsteroidal anti-inflammatory drug interactions. J Clin Psychopharmacol. 1990 Oct;10(5):350-4. [PubMed:2258452 ]
  2. 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 ]
  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 ]