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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014889
Secondary Accession Numbers
  • HMDB14889
Metabolite Identification
Common NameEpinastine
DescriptionEpinastine is used for the prevention of itching associated with allergic conjunctivitis. It has a multi-action effect that inhibits the allergic response in 3 ways: 1. stabilizes mast cells by preventing mast cell degranulation to control the allergic response, 2. prevents histamine binding to both the H1- and H2-receptors to stop itching and provide lasting protection, and 3. prevents the release of proinflammatory chemical mediators from the blood vessel to halt progression of the allergic response.
Structure
Data?1582753232
Synonyms
ValueSource
(+-)-EpinastineChEBI
3-Amino-9,13b-dihydro-1H-dibenz(c,F)imidazo(1,5-a)azepineChEBI
EpinastinaChEBI
EpinastinumChEBI
PurivistKegg
WAL 801 CLHMDB
FlurinolHMDB
WAL 801HMDB
3-Amino-9,13b-dihydro-1H-benz(c,F)imidazo(1,5a)azepineHMDB
WAL 80HMDB
WAL 801CLHMDB
WAL-80 CLHMDB
Epinastine hydrochlorideHMDB
Chemical FormulaC16H15N3
Average Molecular Weight249.3104
Monoisotopic Molecular Weight249.126597495
IUPAC Name2,4-diazatetracyclo[12.4.0.0²,⁶.0⁷,¹²]octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine
Traditional Nameepinastine
CAS Registry Number80012-43-7
SMILES
NC1=NCC2N1C1=CC=CC=C1CC1=CC=CC=C21
InChI Identifier
InChI=1S/C16H15N3/c17-16-18-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)19(15)16/h1-8,15H,9-10H2,(H2,17,18)
InChI KeyWHWZLSFABNNENI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Azepine
  • Benzenoid
  • 2-imidazoline
  • Guanidine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • 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 Point205 - 208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.16 g/LNot Available
LogP3.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.53ALOGPS
logP3.07ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity76.9 m³·mol⁻¹ChemAxon
Polarizability27.33 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.61631661259
DarkChem[M-H]-155.66631661259
DeepCCS[M-2H]-185.02930932474
DeepCCS[M+Na]+160.5530932474
AllCCS[M+H]+158.132859911
AllCCS[M+H-H2O]+154.132859911
AllCCS[M+NH4]+161.732859911
AllCCS[M+Na]+162.832859911
AllCCS[M-H]-164.232859911
AllCCS[M+Na-2H]-163.432859911
AllCCS[M+HCOO]-162.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EpinastineNC1=NCC2N1C1=CC=CC=C1CC1=CC=CC=C213770.1Standard polar33892256
EpinastineNC1=NCC2N1C1=CC=CC=C1CC1=CC=CC=C212480.4Standard non polar33892256
EpinastineNC1=NCC2N1C1=CC=CC=C1CC1=CC=CC=C212502.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epinastine,1TMS,isomer #1C[Si](C)(C)NC1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N122520.7Semi standard non polar33892256
Epinastine,1TMS,isomer #1C[Si](C)(C)NC1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N122437.7Standard non polar33892256
Epinastine,1TMS,isomer #1C[Si](C)(C)NC1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N123531.3Standard polar33892256
Epinastine,2TMS,isomer #1C[Si](C)(C)N(C1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N12)[Si](C)(C)C2476.9Semi standard non polar33892256
Epinastine,2TMS,isomer #1C[Si](C)(C)N(C1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N12)[Si](C)(C)C2566.6Standard non polar33892256
Epinastine,2TMS,isomer #1C[Si](C)(C)N(C1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N12)[Si](C)(C)C3406.5Standard polar33892256
Epinastine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N122695.9Semi standard non polar33892256
Epinastine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N122687.9Standard non polar33892256
Epinastine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N123616.0Standard polar33892256
Epinastine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N12)[Si](C)(C)C(C)(C)C2790.6Semi standard non polar33892256
Epinastine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N12)[Si](C)(C)C(C)(C)C3079.2Standard non polar33892256
Epinastine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NCC2C3=CC=CC=C3CC3=CC=CC=C3N12)[Si](C)(C)C(C)(C)C3471.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epinastine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0590000000-b39e6b7f0c2561681ad32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epinastine 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 - Epinastine 10V, Positive-QTOFsplash10-0udi-0190000000-55c54a74af25de5a147f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 20V, Positive-QTOFsplash10-0udi-0190000000-2580dd8e371096c1da4a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 40V, Positive-QTOFsplash10-0006-1910000000-f127e2e859edf1b82bbd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 10V, Negative-QTOFsplash10-0002-0090000000-02a99c90b5e69ce7b0842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 20V, Negative-QTOFsplash10-0002-1090000000-d764b0b1b1062388fef52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 40V, Negative-QTOFsplash10-0006-9000000000-a161a19c732b38bb4e052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 10V, Positive-QTOFsplash10-0udi-0090000000-f0b3b54c94f5a6ad829d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 20V, Positive-QTOFsplash10-0udi-0090000000-f0b3b54c94f5a6ad829d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 40V, Positive-QTOFsplash10-0kgo-1390000000-f843e3127e653c3dda622021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 10V, Negative-QTOFsplash10-0002-0090000000-a6a269e69e0ce0f0732e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 20V, Negative-QTOFsplash10-0002-0090000000-e4df2bacabe4262b8e2e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinastine 40V, Negative-QTOFsplash10-0006-9460000000-42957781cd670390aa212021-10-11Wishart 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 DB00751 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00751 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00751
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3128
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpinastine
METLIN IDNot Available
PubChem Compound3241
PDB IDNot Available
ChEBI ID51032
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 References
  1. Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. [PubMed:1972625 ]
  2. Schilling JC, Adamus WS, Kuthan H: Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers. Int J Clin Pharmacol Ther Toxicol. 1990 Dec;28(12):493-7. [PubMed:1982280 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 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 monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
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 G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [PubMed:8836655 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular weight:
40097.7
References
  1. Bielory L, Ghafoor S: Histamine receptors and the conjunctiva. Curr Opin Allergy Clin Immunol. 2005 Oct;5(5):437-40. [PubMed:16131920 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:
HTR7
Uniprot ID:
P34969
Molecular weight:
53554.4
References
  1. Dupont LJ, Pype JL, Meade CJ, DeLeyn P, Deneffe G, Demedts MG, Verleden GM: Epinastine (WAL 801CL) inhibits the electrical field stimulation-induced cholinergic contraction in guinea pig and human airways in vitro. Eur Respir J. 1999 Nov;14(5):1068-75. [PubMed:10596692 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Dupont LJ, Pype JL, Meade CJ, DeLeyn P, Deneffe G, Demedts MG, Verleden GM: Epinastine (WAL 801CL) inhibits the electrical field stimulation-induced cholinergic contraction in guinea pig and human airways in vitro. Eur Respir J. 1999 Nov;14(5):1068-75. [PubMed:10596692 ]
  2. Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [PubMed:8836655 ]
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. Tsujii T, Yamamoto E, Ohira T, Saito N, Watanabe S: Effects of sedative and non-sedative H1 antagonists on cognitive tasks: behavioral and near-infrared spectroscopy (NIRS) examinations. Psychopharmacology (Berl). 2007 Sep;194(1):83-91. Epub 2007 May 30. [PubMed:17534605 ]
  2. Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. [PubMed:1972625 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [PubMed:8836655 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Ishiguro N, Nozawa T, Tsujihata A, Saito A, Kishimoto W, Yokoyama K, Yotsumoto T, Sakai K, Igarashi T, Tamai I: Influx and efflux transport of H1-antagonist epinastine across the blood-brain barrier. Drug Metab Dispos. 2004 May;32(5):519-24. [PubMed:15100174 ]