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Dimethindene

July 24, 2017
Common Name

Dimethindene Description

Dimethindene is only found in individuals that have used or taken this drug. It is an antihistamine/anticholinergic used orally and locally as an antipruritic.Dimethindene is a selective histamine H1 antagonist and binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+/-)-dimetahindeneHMDB DimethylpyrindeneHMDB Dimethindene maleateMeSH DimetindeneMeSH Maleate, dimethindeneMeSH DimethpyrindeneMeSH FenistilMeSH ForhistalMeSH Novartis brand OF dimethindene maleateMeSH

Chemical Formlia

C20H24N2 Average Molecliar Weight

292.418 Monoisotopic Molecliar Weight

292.193948778 IUPAC Name

dimethyl(2-{3-[1-(pyridin-2-yl)ethyl]-1H-inden-2-yl}ethyl)amine Traditional Name

dimethindene CAS Registry Number

5636-83-9 SMILES

CC(C1=C(CCN(C)C)CC2=CC=CC=C12)C1=CC=CC=N1

InChI Identifier

InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3

InChI Key

MVMQESMQSYOVGV-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as indenes and isoindenes. These are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring). Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Indenes and isoindenes Direct Parent

Indenes and isoindenes Alternative Parents

  • Pyridines and derivatives
  • Heteroaromatic compounds
  • Trialkylamines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Indene
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Allergic Agents
  • Anticholinergics
  • Antihistamines
  • Antipruritics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.038 mg/mLALOGPS logP4.03ALOGPS logP3.74ChemAxon logS-3.9ALOGPS pKa (Strongest Acidic)18.93ChemAxon pKa (Strongest Basic)9.7ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area16.13 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity93.57 m3·mol-1ChemAxon Polarizability34.9 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

  • 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 DB08801

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08801

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB08801 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

    20541 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Dimetindene NuGOwiki Link

    HMDB15691 Metagene Link

    HMDB15691 METLIN ID

    Not Available PubChem Compound

    21855 PDB ID

    Not Available ChEBI ID

    126443

    Product: Zinc Pyrithione

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Lambrecht G, Gross J, Mutschler E: Neuronal soma-dendritic and prejunctional M1-M4 receptors in gastrointestinal and genitourinary smooth muscle. Life Sci. 1999;64(6-7):403-10. [PubMed:10069503 ]
    2. Novartis Pamphlet [Link]

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
    Gene Name:
    HRH1
    Uniprot ID:
    P35367
    Molecular weight:
    55783.6
    References
    1. Moree WJ, Li BF, Zamani-Kord S, Yu J, Coon T, Huang C, Marinkovic D, Tucci FC, Malany S, Bradbury MJ, Hernandez LM, Wen J, Wang H, Hoare SR, Petroski RE, Jalali K, Yang C, Sacaan A, Madan A, Crowe PD, Beaton G: Identification of a novel selective H1-antihistamine with optimized pharmacokinetic properties for clinical evaluation in the treatment of insomnia. Bioorg Med Chem Lett. 2010 Oct 1;20(19):5874-8. doi: 10.1016/j.bmcl.2010.07.117. Epub 2010 Aug 3. [PubMed:20800486 ]
    2. Pfaff O, Hildebrandt C, Waelbroeck M, Hou X, Moser U, Mutschler E, Lambrecht G: The (S)-(+)-enantiomer of dimethindene: a novel M2-selective muscarinic receptor antagonist. Eur J Pharmacol. 1995 Nov 24;286(3):229-40. [PubMed:8608784 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
    Gene Name:
    CHRM2
    Uniprot ID:
    P08172
    Molecular weight:
    51714.6
    References
    1. Pfaff O, Hildebrandt C, Waelbroeck M, Hou X, Moser U, Mutschler E, Lambrecht G: The (S)-(+)-enantiomer of dimethindene: a novel M2-selective muscarinic receptor antagonist. Eur J Pharmacol. 1995 Nov 24;286(3):229-40. [PubMed:8608784 ]

    PMID: 15476952

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