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Identification
NameAprindine
Accession NumberDB01429
TypeSmall Molecule
GroupsApproved
DescriptionA cardiac depressant used in arrhythmias. [PubChem]
Structure
Thumb
Synonyms
Aprindina
Aprindine
Aprindinum
Compound 99170
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AspenonNot Available
FibocilLilly
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Aprindine hydrochloride
ThumbNot applicableDBSALT000917
Categories
UNII5Y48085P9Q
CAS number37640-71-4
WeightAverage: 322.487
Monoisotopic: 322.24089897
Chemical FormulaC22H30N2
InChI KeyNZLBHDRPUJLHCE-UHFFFAOYSA-N
InChI
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
IUPAC Name
N-[3-(diethylamino)propyl]-N-phenyl-2,3-dihydro-1H-inden-2-amine
SMILES
CCN(CC)CCCN(C1CC2=CC=CC=C2C1)C1=CC=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium channel protein type 5 subunit alphaProteinyes
inhibitor
HumanQ14524 details
CalmodulinProteinunknown
inhibitor
HumanP62158 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Aprindine can be increased when it is combined with Abiraterone.Approved
AmiodaroneThe metabolism of Aprindine can be decreased when combined with Amiodarone.Approved, Investigational
ArtemetherThe metabolism of Aprindine can be decreased when combined with Artemether.Approved
AtomoxetineThe metabolism of Aprindine can be decreased when combined with Atomoxetine.Approved
BetaxololThe metabolism of Aprindine can be decreased when combined with Betaxolol.Approved
BupropionThe metabolism of Aprindine can be decreased when combined with Bupropion.Approved
CelecoxibThe metabolism of Aprindine can be decreased when combined with Celecoxib.Approved, Investigational
ChloroquineThe metabolism of Aprindine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Aprindine can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Aprindine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Aprindine can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Aprindine can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Aprindine can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Aprindine can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Aprindine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Aprindine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe metabolism of Aprindine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Aprindine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Aprindine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Aprindine can be decreased when combined with Cocaine.Approved, Illicit
DarifenacinThe metabolism of Aprindine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Aprindine can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Aprindine can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Aprindine can be decreased when combined with Desipramine.Approved
DiphenhydramineThe metabolism of Aprindine can be decreased when combined with Diphenhydramine.Approved
DronedaroneThe metabolism of Aprindine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Aprindine can be decreased when combined with Duloxetine.Approved
EliglustatThe metabolism of Aprindine can be decreased when combined with Eliglustat.Approved
FluoxetineThe metabolism of Aprindine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Aprindine can be decreased when combined with Fluvoxamine.Approved, Investigational
HaloperidolThe metabolism of Aprindine can be decreased when combined with Haloperidol.Approved
ImipramineThe metabolism of Aprindine can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Aprindine can be decreased when combined with Indinavir.Approved
IsoniazidThe metabolism of Aprindine can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Aprindine can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe metabolism of Aprindine can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Aprindine can be decreased when combined with Lorcaserin.Approved
LumefantrineThe metabolism of Aprindine can be decreased when combined with Lumefantrine.Approved
MethadoneThe metabolism of Aprindine can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Aprindine can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe metabolism of Aprindine can be decreased when combined with Metoprolol.Approved, Investigational
MirabegronThe metabolism of Aprindine can be decreased when combined with Mirabegron.Approved
NevirapineThe metabolism of Aprindine can be decreased when combined with Nevirapine.Approved
NicardipineThe metabolism of Aprindine can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Aprindine can be decreased when combined with Nilotinib.Approved, Investigational
PanobinostatThe serum concentration of Aprindine can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Aprindine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Aprindine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PromazineThe metabolism of Aprindine can be decreased when combined with Promazine.Approved, Vet Approved
QuinidineThe metabolism of Aprindine can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Aprindine can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of Aprindine can be decreased when combined with Ranolazine.Approved, Investigational
RitonavirThe metabolism of Aprindine can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Aprindine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Aprindine can be decreased when combined with Ropinirole.Approved, Investigational
SertralineThe metabolism of Aprindine can be decreased when combined with Sertraline.Approved
StiripentolThe metabolism of Aprindine can be decreased when combined with Stiripentol.Approved
TerbinafineThe metabolism of Aprindine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
ThioridazineThe metabolism of Aprindine can be decreased when combined with Thioridazine.Approved
TiclopidineThe metabolism of Aprindine can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Aprindine can be decreased when combined with Tipranavir.Approved, Investigational
TranylcypromineThe metabolism of Aprindine can be decreased when combined with Tranylcypromine.Approved
VenlafaxineThe metabolism of Aprindine can be decreased when combined with Venlafaxine.Approved
ZiprasidoneThe metabolism of Aprindine can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

Vanhoof, P. and Clarebout, P.; British Patent 1,321,424; June 27, 1973; assigned to Manufac-
ture de Produits Pharmaceutiques A. Christiaens, SA

General ReferencesNot Available
External Links
ATC CodesC01BB04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9925
Blood Brain Barrier+0.9776
Caco-2 permeable+0.7047
P-glycoprotein substrateSubstrate0.6441
P-glycoprotein inhibitor IInhibitor0.7951
P-glycoprotein inhibitor IIInhibitor0.5188
Renal organic cation transporterInhibitor0.7209
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateInhibitor0.7381
CYP450 2C9 inhibitorNon-inhibitor0.7661
CYP450 2D6 inhibitorInhibitor0.5
CYP450 2C19 inhibitorInhibitor0.5287
CYP450 3A4 inhibitorNon-inhibitor0.7571
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8111
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6834
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.4059 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7928
hERG inhibition (predictor II)Inhibitor0.7202
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point120-121 °CVanhoof, P. and Clarebout, P.; British Patent 1,321,424; June 27, 1973; assigned to Manufacture de Produits Pharmaceutiques A. Christiaens, SA
logP4.86HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00782 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
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity involved in sa node cell action potential
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 respon...
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Titin binding
Specific Function:
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins 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 CCP110 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:
16837.47 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase 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 Da
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 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction.
Gene Name:
ORM1
Uniprot ID:
P02763
Molecular Weight:
23511.38 Da
References
  1. Teirlynck O, Belpaire FM, Andreasen F: Binding of aprindine and moxaprindine to human serum, alpha 1-acid glycoprotein and serum of healthy and diseased humans. Eur J Clin Pharmacol. 1982;21(5):427-31. [PubMed:7075647 ]
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Drug created on July 24, 2007 07:04 / Updated on August 17, 2016 12:23