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Emedastine

July 24, 2017
Common Name

Emedastine Description

Emedastine is only found in individuals that have used or taken this drug. It is an antihistamine used in eye drops to treat allergic conjunctivitis. [Wikipedia]Emedastine is a relatively selective, histamine H1 antagonist. In vitro examinations of emedastines affinity for histamine receptors demonstrate relative selectivity for the H1 histamine receptor. In vivo studies have shown concentration-dependent inhibition of histamine-stimliated vascliar permeability in the conjunctiva following topical ocliar administration. Emedastine appears to be devoid of effects on adrenergic, dopaminergic and serotonin receptors. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 1-(2-Ethoxy-ethyl)-2-(4-methyl-[1,4]diazepan-1-yl)-1H-benzoimidazoleChEBI 1-(2-Ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)benzimidazoleChEBI 1-[2-(Ethoxy)ethyl]-2-(4-methyl-1-homopiperazinyl)benzimidazoleChEBI EmedastinaChEBI EmedastinumChEBI Emedastine difumarateHMDB EmadineMeSH 1-(2-Ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarateMeSH

Chemical Formlia

C17H26N4O Average Molecliar Weight

302.4145 Monoisotopic Molecliar Weight

302.210661474 IUPAC Name

1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-1,3-benzodiazole Traditional Name

emedastine CAS Registry Number

87233-61-2 SMILES

CCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC1

InChI Identifier

InChI=1S/C17H26N4O/c1-3-22-14-13-21-16-8-5-4-7-15(16)18-17(21)20-10-6-9-19(2)11-12-20/h4-5,7-8H,3,6,9-14H2,1-2H3

InChI Key

KBUZBQVCBVDWKX-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds). Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Benzimidazoles Direct Parent

Benzimidazoles Alternative Parents

  • Dialkylarylamines
  • 1,4-diazepanes
  • N-substituted imidazoles
  • Benzenoids
  • Aminoimidazoles
  • Heteroaromatic compounds
  • Trialkylamines
  • Dialkyl ethers
  • Azacyclic compounds
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Benzimidazole
  • Dialkylarylamine
  • Diazepane
  • 1,4-diazepane
  • Aminoimidazole
  • N-substituted imidazole
  • Benzenoid
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Dialkyl ether
  • Azacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • benzimidazoles (CHEBI:4779 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Allergic Agents
  • Histamine H1 Antagonists

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.44e+00 g/LNot Available LogP2.6Not Available

    Predicted Properties

    Property Value Source Water Solubility1.44 mg/mLALOGPS logP2.91ALOGPS logP2.49ChemAxon logS-2.3ALOGPS pKa (Strongest Basic)8.68ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area33.53 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity90.47 m3·mol-1ChemAxon Polarizability35.49 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 DB01084

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01084

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01084 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

    3106 KEGG Compound ID

    C07785 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Emedastine NuGOwiki Link

    HMDB15216 Metagene Link

    HMDB15216 METLIN ID

    Not Available PubChem Compound

    3219 PDB ID

    Not Available ChEBI ID

    4779

    Product: EG00230

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

    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. Sharif NA, Su SX, Yanni JM: Emedastine: a potent, high affinity histamine H1-receptor-selective antagonist for ocular use: receptor binding and second messenger studies. J Ocul Pharmacol. 1994 Winter;10(4):653-64. [PubMed:7714409 ]
    2. Yanni JM, Stephens DJ, Parnell DW, Spellman JM: Preclinical efficacy of emedastine, a potent, selective histamine H1 antagonist for topical ocular use. J Ocul Pharmacol. 1994 Winter;10(4):665-75. [PubMed:7714410 ]
    3. Inagaki N, Sakurai T, Abe T, Musoh K, Kawasaki H, Tsunematsu M, Nagai H: Characterization of antihistamines using biphasic cutaneous reaction in BALB/c mice. Life Sci. 1998;63(11):PL 145-50. [PubMed:9747899 ]
    4. Murota H, Katayama I: Emedastine difumarate: a review of its potential ameliorating effect for tissue remodeling in allergic diseases. Expert Opin Pharmacother. 2009 Aug;10(11):1859-67. doi: 10.1517/14656560903078410. [PubMed:19558341 ]
    5. Corrado ME, Radicioni MM, Hartwig J, Assandri A, Oldeman HG, Mion A: Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus terfenadine in the treatment of seasonal allergic rhinitis. Arzneimittelforschung. 2004;54(10):660-5. [PubMed:15553105 ]
    6. Murota H, Bae S, Hamasaki Y, Maruyama R, Katayama I: Emedastine difumarate inhibits histamine-induced collagen synthesis in dermal fibroblasts. J Investig Allergol Clin Immunol. 2008;18(4):245-52. [PubMed:18714531 ]
    7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 21307853

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