Emedastine

Identification

Summary

Emedastine is a selective H1-receptor antagonist used topically to manage symptoms of allergic conjunctivitis.

Brand Names
Emadine
Generic Name
Emedastine
DrugBank Accession Number
DB01084
Background

Emedastine is an antihistamine used in eye drops to treat allergic conjunctivitis.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 302.4145
Monoisotopic: 302.210661474
Chemical Formula
C17H26N4O
Synonyms
  • 1-(2-Ethoxy-ethyl)-2-(4-methyl-[1,4]diazepan-1-yl)-1H-benzoimidazole
  • 1-(2-ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)benzimidazole
  • 1-[2-(ethoxy)ethyl]-2-(4-methyl-1-homopiperazinyl)benzimidazole
  • Emedastina
  • Emedastine
  • Emedastinum

Pharmacology

Indication

For the temporary relief of the signs and symptoms of allergic conjunctivitis.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAllergic conjunctivitis••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Emedastine is a relatively selective H1-receptor antagonist.

Mechanism of action

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 exert negligible effects on adrenergic, dopaminergic and serotonin receptors.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
Absorption

Ophthalmic use of emedastine usually does not produce measurable plasma concentrations.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Two primary metabolites, 5-hydroxyemedastine and 6-hydroxyemedastine, are excreted in the urine as both free and conjugated forms. Minor metabolites include the 5'-oxoanalogs of 5-hydroxyemedastine and 6-hydroxy-emedastine and the N-oxide.

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Route of elimination

Following oral administration, approximately 44% of the total dose can be recovered in the urine over the 24-hour period, with only 3.6% of the dose excreted as unchanged form. Two primary metabolites, 5- and 6-hydroxyemedastine, are excreted in the urine as both free and conjugated forms.

Half-life

The elimination half-life in the plasma is 3-4 hours following oral administration.

Clearance

Not Available

Adverse Effects
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Toxicity

Somnolence and malaise have been reported following daily oral administration.

Pathways
PathwayCategory
Emedastine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Emedastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Emedastine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Emedastine.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Emedastine.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Emedastine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Emedastine difumarate42MB94QOSM87233-62-3FWLKKPKZQYVAFR-LVEZLNDCSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EmadineSolution / drops0.05 %OphthalmicNovartis Europharm Limited2016-09-08Not applicableEU flag
EmadineSolution / drops0.05 %OphthalmicNovartis Europharm Limited2016-09-08Not applicableEU flag
EmadineSolution / drops0.5 mg/1mLOphthalmicALCON LABORATORIES, INC.1998-02-15Not applicableUS flag
EmadineSolution / drops0.05 %OphthalmicNovartis Europharm Limited2016-09-08Not applicableEU flag
EmadineSolution / drops0.05 %OphthalmicNovartis Europharm Limited2016-09-08Not applicableEU flag

Categories

ATC Codes
S01GX06 — Emedastine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Not Available
Direct Parent
Benzimidazoles
Alternative Parents
Dialkylarylamines / 1,4-diazepanes / N-substituted imidazoles / Benzenoids / Aminoimidazoles / Heteroaromatic compounds / Trialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds
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Substituents
1,4-diazepane / Amine / Aminoimidazole / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Dialkyl ether / Dialkylarylamine
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzimidazoles (CHEBI:4779)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
9J1H7Y9OJV
CAS number
87233-61-2
InChI Key
KBUZBQVCBVDWKX-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-1,3-benzodiazole
SMILES
CCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC1

References

General References
Not Available
Human Metabolome Database
HMDB0015216
KEGG Drug
D07890
KEGG Compound
C07785
PubChem Compound
3219
PubChem Substance
46505109
ChemSpider
3106
BindingDB
50019624
RxNav
28144
ChEBI
4779
ChEMBL
CHEMBL594
ZINC
ZINC000001530912
Therapeutic Targets Database
DAP001067
PharmGKB
PA164751802
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Emedastine
FDA label
Download (101 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentAllergic Rhinitis (AR)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Alcon Laboratories
Dosage Forms
FormRouteStrength
LiquidOphthalmic0.05 %
Solution / dropsIntraocular0.5 mg/ml
Solution / dropsOphthalmic0.05 %
Solution / dropsOphthalmic0.5 mg/1mL
SolutionOphthalmic
SolutionOphthalmic0.5 mg/ml
Solution / dropsOphthalmic
Capsule, extended releaseOphthalmic
PatchTransdermal4 mg
PatchTransdermal8 mg
Prices
Unit descriptionCostUnit
Emadine 0.05% Solution 5ml Bottle78.75USD bottle
Emadine 0.05% eye drops15.58USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5441958No1995-08-152013-12-08US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySoluble (difumarate formulation)Not Available
logP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP2.91ALOGPS
logP2.49Chemaxon
logS-2.3ALOGPS
pKa (Strongest Basic)8.66Chemaxon
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
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.959
Caco-2 permeable+0.5351
P-glycoprotein substrateSubstrate0.7487
P-glycoprotein inhibitor IInhibitor0.7448
P-glycoprotein inhibitor IIInhibitor0.6697
Renal organic cation transporterInhibitor0.5644
CYP450 2C9 substrateNon-substrate0.8578
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6537
CYP450 1A2 substrateInhibitor0.6261
CYP450 2C9 inhibitorNon-inhibitor0.7292
CYP450 2D6 inhibitorNon-inhibitor0.7128
CYP450 2C19 inhibitorNon-inhibitor0.5594
CYP450 3A4 inhibitorNon-inhibitor0.8535
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5815
Ames testNon AMES toxic0.7054
CarcinogenicityNon-carcinogens0.9076
BiodegradationNot ready biodegradable0.9931
Rat acute toxicity2.6743 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Inhibitor0.5805
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-004i-7290000000-403c6f7ea26245b8aa3d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0029000000-7e682087c893f1ec1211
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0029000000-7f436d47ab18bdfffd55
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfr-0196000000-6d0d05b18e8d3ee33177
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0159000000-c9fcf44572c77ecd89b2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0036-0590000000-0da531aed4c46d34dcb6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05mk-0950000000-fe28e09c834763b800f9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.5612162
predicted
DarkChem Lite v0.1.0
[M-H]-169.21933
predicted
DeepCCS 1.0 (2019)
[M+H]+180.2777162
predicted
DarkChem Lite v0.1.0
[M+H]+171.57732
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.2175162
predicted
DarkChem Lite v0.1.0
[M+Na]+177.67047
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
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 catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:22