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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:35 UTC
HMDB IDHMDB0014338
Secondary Accession Numbers
  • HMDB14338
Metabolite Identification
Common NameIndecainide
DescriptionIndecainide is only found in individuals that have used or taken this drug. It is a rarely used antidysrhythmic. Indecainide has local anesthetic activity and belongs to the membrane stabilizing (Class 1) group of antiarrhythmic agents; it has electrophysiologic effects characteristic of the IC class of antiarrhythmics.Indecainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers.
Structure
Data?1582753167
Synonyms
ValueSource
9-(3-(Isopropylamino)propyl))fluorene-9-carboxamideHMDB
9-(3-(Isopropylamino)propyl)-9-fluorenylcarboxamidHMDB
RicainidHMDB
RicainideHMDB
9-(3-((1-Methylethyl)amino)propyl)-9H-fluorene-9-carboxamideHMDB
Indecainide hydrochlorideHMDB
9-{3-[(propan-2-yl)amino]propyl}-9H-fluorene-9-carboximidateHMDB
IndecainideMeSH
Chemical FormulaC20H24N2O
Average Molecular Weight308.4174
Monoisotopic Molecular Weight308.1888634
IUPAC Name9-{3-[(propan-2-yl)amino]propyl}-9H-fluorene-9-carboxamide
Traditional Nameindecainide
CAS Registry Number74517-78-5
SMILES
CC(C)NCCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C12
InChI Identifier
InChI=1S/C20H24N2O/c1-14(2)22-13-7-12-20(19(21)23)17-10-5-3-8-15(17)16-9-4-6-11-18(16)20/h3-6,8-11,14,22H,7,12-13H2,1-2H3,(H2,21,23)
InChI KeyUCEWGESNIULAGX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassFluorenes
Sub ClassNot Available
Direct ParentFluorenes
Alternative Parents
Substituents
  • Delta amino acid or derivatives
  • Fluorene
  • Aralkylamine
  • Fatty amide
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxamide group
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Secondary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point94 - 95 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0009 g/LNot Available
LogP3.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0009 g/LALOGPS
logP3.24ALOGPS
logP3.26ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)16.51ChemAxon
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.05 m³·mol⁻¹ChemAxon
Polarizability35.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.54531661259
DarkChem[M-H]-171.68831661259
DeepCCS[M-2H]-205.05430932474
DeepCCS[M+Na]+180.6230932474
AllCCS[M+H]+175.632859911
AllCCS[M+H-H2O]+172.532859911
AllCCS[M+NH4]+178.532859911
AllCCS[M+Na]+179.332859911
AllCCS[M-H]-180.332859911
AllCCS[M+Na-2H]-180.432859911
AllCCS[M+HCOO]-180.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IndecainideCC(C)NCCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C123758.3Standard polar33892256
IndecainideCC(C)NCCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C122808.0Standard non polar33892256
IndecainideCC(C)NCCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C122543.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indecainide,1TMS,isomer #1CC(C)NCCCC1(C(=O)N[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C212540.1Semi standard non polar33892256
Indecainide,1TMS,isomer #1CC(C)NCCCC1(C(=O)N[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C212657.0Standard non polar33892256
Indecainide,1TMS,isomer #1CC(C)NCCCC1(C(=O)N[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C213051.6Standard polar33892256
Indecainide,1TMS,isomer #2CC(C)N(CCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C2771.3Semi standard non polar33892256
Indecainide,1TMS,isomer #2CC(C)N(CCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C2776.4Standard non polar33892256
Indecainide,1TMS,isomer #2CC(C)N(CCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C3433.4Standard polar33892256
Indecainide,2TMS,isomer #1CC(C)N(CCCC1(C(=O)N[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C2716.6Semi standard non polar33892256
Indecainide,2TMS,isomer #1CC(C)N(CCCC1(C(=O)N[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C2849.4Standard non polar33892256
Indecainide,2TMS,isomer #1CC(C)N(CCCC1(C(=O)N[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C2994.6Standard polar33892256
Indecainide,2TMS,isomer #2CC(C)NCCCC1(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C212615.9Semi standard non polar33892256
Indecainide,2TMS,isomer #2CC(C)NCCCC1(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C212832.6Standard non polar33892256
Indecainide,2TMS,isomer #2CC(C)NCCCC1(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C212933.1Standard polar33892256
Indecainide,3TMS,isomer #1CC(C)N(CCCC1(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C2872.6Semi standard non polar33892256
Indecainide,3TMS,isomer #1CC(C)N(CCCC1(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C3001.9Standard non polar33892256
Indecainide,3TMS,isomer #1CC(C)N(CCCC1(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C2855.4Standard polar33892256
Indecainide,1TBDMS,isomer #1CC(C)NCCCC1(C(=O)N[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C212754.2Semi standard non polar33892256
Indecainide,1TBDMS,isomer #1CC(C)NCCCC1(C(=O)N[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C212923.9Standard non polar33892256
Indecainide,1TBDMS,isomer #1CC(C)NCCCC1(C(=O)N[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C213143.1Standard polar33892256
Indecainide,1TBDMS,isomer #2CC(C)N(CCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3045.7Semi standard non polar33892256
Indecainide,1TBDMS,isomer #2CC(C)N(CCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3002.4Standard non polar33892256
Indecainide,1TBDMS,isomer #2CC(C)N(CCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3483.9Standard polar33892256
Indecainide,2TBDMS,isomer #1CC(C)N(CCCC1(C(=O)N[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3208.7Semi standard non polar33892256
Indecainide,2TBDMS,isomer #1CC(C)N(CCCC1(C(=O)N[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3319.7Standard non polar33892256
Indecainide,2TBDMS,isomer #1CC(C)N(CCCC1(C(=O)N[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3154.3Standard polar33892256
Indecainide,2TBDMS,isomer #2CC(C)NCCCC1(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C213098.6Semi standard non polar33892256
Indecainide,2TBDMS,isomer #2CC(C)NCCCC1(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C213266.0Standard non polar33892256
Indecainide,2TBDMS,isomer #2CC(C)NCCCC1(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C213067.6Standard polar33892256
Indecainide,3TBDMS,isomer #1CC(C)N(CCCC1(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3544.7Semi standard non polar33892256
Indecainide,3TBDMS,isomer #1CC(C)N(CCCC1(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3608.7Standard non polar33892256
Indecainide,3TBDMS,isomer #1CC(C)N(CCCC1(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3082.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Indecainide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9050000000-db950638d7d29670ba202017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indecainide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 10V, Positive-QTOFsplash10-0a4i-0097000000-e32e5cd63606a048f6a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 20V, Positive-QTOFsplash10-0udl-0090000000-f98d11abb5179d17d8472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 40V, Positive-QTOFsplash10-052f-9130000000-392bd0f5b66da6e104aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 10V, Negative-QTOFsplash10-0a4i-0019000000-291a4ed87d22ee4d2eae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 20V, Negative-QTOFsplash10-0a4i-4097000000-58e95d035724a140ed6d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 40V, Negative-QTOFsplash10-0006-9010000000-cb7c81bf4feffefc75dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 10V, Positive-QTOFsplash10-0a4i-0059000000-f9ce8ad3e2092a5c1dac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 20V, Positive-QTOFsplash10-0a4i-0494000000-440be10bacbf5748c9f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 40V, Positive-QTOFsplash10-002b-4920000000-6a4d2018e5a92016840b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 10V, Negative-QTOFsplash10-0a4i-0009000000-229b7f1e3c92833e7c332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 20V, Negative-QTOFsplash10-08fs-0190000000-72e560ee1bb9a114291b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indecainide 40V, Negative-QTOFsplash10-0007-1920000000-34d197d17de2c33986592021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00192 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00192 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00192
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID47194
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndecainide
METLIN IDNot Available
PubChem Compound52195
PDB IDNot Available
ChEBI ID775193
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Giardina EV, Saroff AL, Schneider M: Effect of indecainide in patients with left ventricular dysfunction. Clin Pharmacol Ther. 1990 Nov;48(5):582-9. [PubMed:2225716 ]

Enzymes

General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Jaillon P, Drici M: Recent antiarrhythmic drugs. Am J Cardiol. 1989 Dec 5;64(20):65J-69J. [PubMed:2688391 ]
  5. Holland DR, Lacefield WB, Gonzales CR, Johnston SR, Turk JA: Indecainide: effects on arrhythmias, electrophysiology, and cardiovascular dynamics. J Cardiovasc Pharmacol. 1989 Sep;14(3):454-61. [PubMed:2476626 ]
  6. Steinberg MI, Wiest SA: Electrophysiological studies of indecainide hydrochloride, a new antiarrhythmic agent, in canine cardiac tissues. J Cardiovasc Pharmacol. 1984 Jul-Aug;6(4):614-21. [PubMed:6206315 ]