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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015498
Secondary Accession Numbers
  • HMDB15498
Metabolite Identification
Common NameAprindine
DescriptionAprindine, also known as compound 99170 or fiboran, belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Aprindine is a very strong basic compound (based on its pKa).
Structure
Data?1582753303
Synonyms
ValueSource
Compound 99170HMDB
AprindinHMDB
AprinidineHMDB
Christiaens brand OF aprindine hydrochlorideHMDB
FiboranHMDB
Nycomed brand OF aprindine hydrochlorideHMDB
AmidonalHMDB
PCR Brand OF aprindine hydrochlorideHMDB
Chemical FormulaC22H30N2
Average Molecular Weight322.487
Monoisotopic Molecular Weight322.24089897
IUPAC NameN-[3-(diethylamino)propyl]-N-phenyl-2,3-dihydro-1H-inden-2-amine
Traditional NameN-[3-(diethylamino)propyl]-N-phenyl-2,3-dihydro-1H-inden-2-amine
CAS Registry Number37640-71-4
SMILES
CCN(CC)CCCN(C1CC2=CC=CC=C2C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C22H30N2/c1-3-23(4-2)15-10-16-24(21-13-6-5-7-14-21)22-17-19-11-8-9-12-20(19)18-22/h5-9,11-14,22H,3-4,10,15-18H2,1-2H3
InChI KeyNZLBHDRPUJLHCE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassNot Available
Direct ParentIndanes
Alternative Parents
Substituents
  • Indane
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point120 - 121 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0078 g/LNot Available
LogP4.86HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0078 g/LALOGPS
logP5.58ALOGPS
logP4.99ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)9.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.22 m³·mol⁻¹ChemAxon
Polarizability40.02 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.4731661259
DarkChem[M-H]-177.4731661259
DeepCCS[M+H]+177.86830932474
DeepCCS[M-H]-175.5130932474
DeepCCS[M-2H]-208.39630932474
DeepCCS[M+Na]+184.0230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AprindineCCN(CC)CCCN(C1CC2=CC=CC=C2C1)C1=CC=CC=C13219.2Standard polar33892256
AprindineCCN(CC)CCCN(C1CC2=CC=CC=C2C1)C1=CC=CC=C12504.9Standard non polar33892256
AprindineCCN(CC)CCCN(C1CC2=CC=CC=C2C1)C1=CC=CC=C12430.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aprindine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9581000000-398e96ca144138626ef22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aprindine 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 - Aprindine 10V, Positive-QTOFsplash10-00di-0119000000-0bba42cb527180a4b5b62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 20V, Positive-QTOFsplash10-02mi-2944000000-9acecdd3e695bf7a708f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 40V, Positive-QTOFsplash10-01b9-9820000000-5684566fe54fde3cdaa92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 10V, Negative-QTOFsplash10-00di-0019000000-f9125b405b821f02e9402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 20V, Negative-QTOFsplash10-05fr-2198000000-d4943044e5978a489d7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 40V, Negative-QTOFsplash10-0abc-9540000000-f3b77bb45f18f9b525a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 10V, Positive-QTOFsplash10-00di-0119000000-754d6957909ca916b53c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 20V, Positive-QTOFsplash10-01b9-2935000000-b4cbf2144dbd9f27d31e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 40V, Positive-QTOFsplash10-001r-6900000000-01800133db2598d357732021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 10V, Negative-QTOFsplash10-00di-0009000000-75a8eae5906ccf85d9d92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 20V, Negative-QTOFsplash10-00di-0259000000-5f24c1a0dcf5fd0811612021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprindine 40V, Negative-QTOFsplash10-066r-3980000000-493d2113129e43e1cb7c2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 DB01429 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01429 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01429
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2132
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAprindine
METLIN IDNot Available
PubChem Compound2218
PDB IDNot Available
ChEBI ID784872
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 ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. 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 ]
General function:
Involved in calcium ion binding
Specific function:
Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:
CALM1
Uniprot ID:
P62158
Molecular weight:
16837.5
References
  1. Levine SN, Hollier B: Aprindine inhibits calmodulin-stimulated phosphodiesterase and Ca-ATPase activities. J Cardiovasc Pharmacol. 1983 Jan-Feb;5(1):151-6. [PubMed:6186851 ]
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. Sato R, Hisatome I, Tanaka Y, Sasaki N, Kotake H, Mashiba H, Katori R: Aprindine blocks the sodium current in guinea-pig ventricular myocytes. Naunyn Schmiedebergs Arch Pharmacol. 1991 Sep;344(3):331-6. [PubMed:1660104 ]
  2. Kamiya K, Kodama I, Toyama J: A combination of inactivated sodium channel blockers causes competitive interaction on dV/dtmax of single ventricular myocytes. Cardiovasc Res. 1991 Jun;25(6):516-22. [PubMed:1653644 ]