Identification

Name
Aprindine
Accession Number
DB01429
Type
Small Molecule
Groups
Approved
Description

A cardiac depressant used in arrhythmias. [PubChem]

Structure
Thumb
Synonyms
  • Aprindina
  • Aprindine
  • Aprindinum
  • Compound 99170
Product Ingredients
IngredientUNIICASInChI Key
Aprindine hydrochloridePB5EKT7Q2V33237-74-0KIPFVRHNAAZJOD-UHFFFAOYSA-N
International/Other Brands
Aspenon / Fibocil (Lilly)
Categories
UNII
5Y48085P9Q
CAS number
37640-71-4
Weight
Average: 322.487
Monoisotopic: 322.24089897
Chemical Formula
C22H30N2
InChI Key
NZLBHDRPUJLHCE-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

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ASodium channel protein type 5 subunit alpha
inhibitor
Human
UCalmodulin
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not 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
DosulepinThe metabolism of Aprindine can be decreased when combined with Dosulepin.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
ManidipineThe metabolism of Aprindine can be decreased when combined with Manidipine.Approved, Investigational
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
MidostaurinThe metabolism of Aprindine can be decreased when combined with Midostaurin.Approved
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, Withdrawn
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 Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB15498
KEGG Drug
D01326
PubChem Compound
2218
PubChem Substance
46505478
ChemSpider
2132
ChEBI
135370
ChEMBL
CHEMBL1213033
Therapeutic Targets Database
DAP000954
PharmGKB
PA164764496
Wikipedia
Aprindine
ATC Codes
C01BB04 — Aprindine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)120-121 °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
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Indanes
Sub Class
Not Available
Direct Parent
Indanes
Alternative Parents
Dialkylarylamines / Aniline and substituted anilines / Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
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
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not 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 pr...
Gene Name
SCN5A
Uniprot ID
Q14524
Uniprot Name
Sodium channel protein type 5 subunit alpha
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...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
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...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
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]

Drug created on July 24, 2007 07:04 / Updated on November 09, 2017 02:59