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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:54 UTC
HMDB IDHMDB0015216
Secondary Accession Numbers
  • HMDB15216
Metabolite Identification
Common NameEmedastine
DescriptionEmedastine 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 emedastine's affinity for histamine receptors demonstrate relative selectivity for the H1 histamine receptor. In vivo studies have shown concentration-dependent inhibition of histamine-stimulated vascular permeability in the conjunctiva following topical ocular administration. Emedastine appears to be devoid of effects on adrenergic, dopaminergic and serotonin receptors.
Structure
Data?1582753271
Synonyms
ValueSource
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
EmadineKegg
Emedastine difumarateHMDB
1-(2-Ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarateHMDB
Chemical FormulaC17H26N4O
Average Molecular Weight302.4145
Monoisotopic Molecular Weight302.210661474
IUPAC Name1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-1,3-benzodiazole
Traditional Nameemedastine
CAS Registry Number87233-61-2
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 KeyKBUZBQVCBVDWKX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds 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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.44 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP2.91ALOGPS
logP2.49ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)8.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area33.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.47 m³·mol⁻¹ChemAxon
Polarizability35.49 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.031661259
DarkChem[M-H]-168.61831661259
DeepCCS[M-2H]-202.10530932474
DeepCCS[M+Na]+177.6730932474
AllCCS[M+H]+172.432859911
AllCCS[M+H-H2O]+169.232859911
AllCCS[M+NH4]+175.432859911
AllCCS[M+Na]+176.232859911
AllCCS[M-H]-176.232859911
AllCCS[M+Na-2H]-176.332859911
AllCCS[M+HCOO]-176.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EmedastineCCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC13426.8Standard polar33892256
EmedastineCCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC12357.8Standard non polar33892256
EmedastineCCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC12466.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Emedastine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-7290000000-403c6f7ea26245b8aa3d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Emedastine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Emedastine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 10V, Positive-QTOFsplash10-0udi-0039000000-88d0f578474ee13848dd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 20V, Positive-QTOFsplash10-0zgi-2093000000-4d49f8e693f1a29a43402016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 40V, Positive-QTOFsplash10-00sr-9330000000-ce0a5d1ce6666a00db172016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 10V, Negative-QTOFsplash10-0udi-1059000000-2069d9730b3ab025cd022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 20V, Negative-QTOFsplash10-0fb9-1193000000-10c8f72e647d91eca02d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 40V, Negative-QTOFsplash10-114i-2790000000-42ba1c4128b01cda2e122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 10V, Positive-QTOFsplash10-0udi-0029000000-8a6a03ec309aee4a5b692021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 20V, Positive-QTOFsplash10-0zfr-0098000000-692570c2a4d37d1a187a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 40V, Positive-QTOFsplash10-07fs-1940000000-114d05222c09f73f0b982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 10V, Negative-QTOFsplash10-0udi-0059000000-3fcac4e0104dba0e140d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 20V, Negative-QTOFsplash10-0gvo-0394000000-c3934240bec1a912f7c62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Emedastine 40V, Negative-QTOFsplash10-0hji-0980000000-8d2c0ee402a42d3bd4c32021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01084 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01084 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01084
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3106
KEGG Compound IDC07785
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEmedastine
METLIN IDNot Available
PubChem Compound3219
PDB IDNot Available
ChEBI ID4779
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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 ]