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
Structure for Emedastine (DB01084)
- 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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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - 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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Somnolence and malaise have been reported following daily oral administration.
- Pathways
Pathway Category Emedastine H1-Antihistamine Action Drug 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Emedastine. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Emedastine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Emedastine. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Emedastine. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Emedastine. Amantadine The risk or severity of QTc prolongation can be increased when Amantadine is combined with Emedastine. Amifampridine The risk or severity of QTc prolongation can be increased when Emedastine is combined with Amifampridine. Amiodarone The risk or severity of QTc prolongation can be increased when Emedastine is combined with Amiodarone. Amisulpride The risk or severity of QTc prolongation can be increased when Emedastine is combined with Amisulpride. Amitriptyline The risk or severity of QTc prolongation can be increased when Amitriptyline is combined with Emedastine. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Emedastine difumarate 42MB94QOSM 87233-62-3 FWLKKPKZQYVAFR-LVEZLNDCSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Emadine Solution / drops 0.05 % Ophthalmic Novartis Europharm Limited 2016-09-08 Not applicable EU 
Emadine Solution / drops 0.05 % Ophthalmic Novartis Europharm Limited 2016-09-08 Not applicable EU Emadine Solution / drops 0.05 % Ophthalmic Novartis Europharm Limited 2016-09-08 Not applicable EU Emadine Solution / drops 0.05 % Ophthalmic Novartis Europharm Limited 2016-09-08 Not applicable EU Emadine Solution / drops 0.5 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1998-02-15 Not applicable US 
Emadine Liquid 0.05 % Ophthalmic Alcon, Inc. 1998-08-24 2013-04-01 Canada 
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 show 1 more
- 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
- External Links
- Human Metabolome Database
- HMDB0015216
- KEGG Drug
- D07890
- KEGG Compound
- C07785
- PubChem Compound
- 3219
- PubChem Substance
- 46505109
- ChemSpider
- 3106
- BindingDB
- 50019624
- 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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Alcon Laboratories
- Dosage Forms
Form Route Strength Liquid Ophthalmic 0.05 % Solution / drops Intraocular 0.5 mg/ml Solution / drops Ophthalmic 0.05 % Solution / drops Ophthalmic 0.5 mg/1mL Solution / drops Ophthalmic Solution Ophthalmic Capsule, extended release Ophthalmic Patch Transdermal 4 mg Patch Transdermal 8 mg - Prices
Unit description Cost Unit Emadine 0.05% Solution 5ml Bottle 78.75USD bottle Emadine 0.05% eye drops 15.58USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5441958 No 1995-08-15 2013-12-08 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble (difumarate formulation) Not Available logP 2.6 Not Available - Predicted Properties
Property Value Source Water Solubility 1.44 mg/mL ALOGPS logP 2.91 ALOGPS logP 2.49 ChemAxon logS -2.3 ALOGPS pKa (Strongest Basic) 8.68 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 33.53 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 90.47 m3·mol-1 ChemAxon Polarizability 35.49 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.959 Caco-2 permeable + 0.5351 P-glycoprotein substrate Substrate 0.7487 P-glycoprotein inhibitor I Inhibitor 0.7448 P-glycoprotein inhibitor II Inhibitor 0.6697 Renal organic cation transporter Inhibitor 0.5644 CYP450 2C9 substrate Non-substrate 0.8578 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6537 CYP450 1A2 substrate Inhibitor 0.6261 CYP450 2C9 inhibitor Non-inhibitor 0.7292 CYP450 2D6 inhibitor Non-inhibitor 0.7128 CYP450 2C19 inhibitor Non-inhibitor 0.5594 CYP450 3A4 inhibitor Non-inhibitor 0.8535 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5815 Ames test Non AMES toxic 0.7054 Carcinogenicity Non-carcinogens 0.9076 Biodegradation Not ready biodegradable 0.9931 Rat acute toxicity 2.6743 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5 hERG inhibition (predictor II) Inhibitor 0.5805
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created on June 13, 2005 13:24 / Updated on May 07, 2021 21:22