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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:09 UTC
HMDB IDHMDB15498
Secondary Accession NumbersNone
Metabolite Identification
Common NameAprindine
DescriptionAprindine is only found in individuals that have used or taken this drug. It is a cardiac depressant used in arrhythmias. [PubChem]
Structure
Thumb
Synonyms
ValueSource
Compound 99170ChEMBL
AprindinHMDB
AprinidineHMDB
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 KeyInChIKey=NZLBHDRPUJLHCE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indanes. These 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
  • Dialkylarylamine
  • Aralkylamine
  • Aniline
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Arrhythmia Agents
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point120 - 121 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.82e-03 g/LNot Available
LogP4.86HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0078 mg/mLALOGPS
logP5.58ALOGPS
logP4.99ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)9.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.22 m3·mol-1ChemAxon
Polarizability40.02 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01429
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01429
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01429
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2132
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAprindine
NuGOwiki LinkHMDB15498
Metagene LinkHMDB15498
METLIN IDNot Available
PubChem Compound2218
PDB IDNot Available
ChEBI ID784872
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. Epub 2009 Nov 24. [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. [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. [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. [1653644 ]