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Aprindine

July 24, 2017
Common Name

Aprindine Description

Aprindine is only found in individuals that have used or taken this drug. It is a cardiac depressant used in arrhythmias. [PubChem] Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Compound 99170ChEMBL AprindinHMDB AprinidineHMDB Christiaens brand OF aprindine hydrochlorideMeSH FiboranMeSH Nycomed brand OF aprindine hydrochlorideMeSH AmidonalMeSH PCR Brand OF aprindine hydrochlorideMeSH

Chemical Formlia

C22H30N2 Average Molecliar Weight

322.487 Monoisotopic Molecliar Weight

322.24089897 IUPAC Name

N-[3-(diethylamino)propyl]-N-phenyl-2,3-dihydro-1H-inden-2-amine Traditional Name

N-[3-(diethylamino)propyl]-N-phenyl-2,3-dihydro-1H-inden-2-amine CAS Registry Number

37640-71-4 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 Key

NZLBHDRPUJLHCE-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as indanes. These are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Indanes 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
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound

    • Molecliar Framework

    Aromatic homopolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Arrhythmia Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point120 – 121 °CNot Available Boiling PointNot AvailableNot Available Water Solubility7.82e-03 g/LNot Available LogP4.86HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01429

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01429

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01429 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2132 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Aprindine NuGOwiki Link

    HMDB15498 Metagene Link

    HMDB15498 METLIN ID

    Not Available PubChem Compound

    2218 PDB ID

    Not Available ChEBI ID

    784872

    Product: Chlorhexidine (digluconate)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not 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 ]

    PMID: 17372190

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