EMEDASTINE MONOFUMARATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H26N4O.C4H4O4
Molecular Weight	418.4867
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CCOCCN1C(=NC2=C1C=CC=C2)N3CCCN(C)CC3

InChI

InChIKey=FGFODSDYSQTNOS-WLHGVMLRSA-N

InChI=1S/C17H26N4O.C4H4O4/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;5-3(6)1-2-4(7)8/h4-5,7-8H,3,6,9-14H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C17H26N4O
Molecular Weight	302.4145
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/20706slr011_emadine_lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19558341

Emedastine is an antihistaminic agent, which was approved by FDA for the treatment of allergic conjunctivitis (Emadine brand name). The drug acts selectively on H1 receptors with lower affinity to H2 and H3 subtypes. Emedastine has a relatively unfavorable CNS effect profile. A small percentage of patients reported somnolence as an adverse effect after administration.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/20706slr011_emadine_lbl.pdf	Antagonist 2849		1.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic conjunctivitis 101 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/20706slr011_emadine_lbl.pdf	Primary		Approved 8583	EMADINE Approved Use EMADINE (emedastine difumarate ophthalmic solution) 0.05% is indicated for the temporary relief of the signs and symptoms of allergic conjunctivitis. Launch Date 1997

C_max

Value	Dose	Analyte	Population
2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	EMEDASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	EMEDASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	EMEDASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	EMEDASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
16.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	EMEDASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
29.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	EMEDASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
24.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	EMEDASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
46.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	EMEDASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
6.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	EMEDASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	EMEDASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	EMEDASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11317479	2 mg 2 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	EMEDASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
4 mg 2 times / day steady, oral Studied dose Dose: 4 mg, 2 times / day Route: oral Route: steady Dose: 4 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11949773/	healthy, 21 - 45 years Health Status: healthy Age Group: 21 - 45 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11949773/	Other AEs: Impaired driving ability... Other AEs: Impaired driving ability (19 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/11949773/
0.05 % 1 times / day steady, ophthalmic Recommended Dose: 0.05 %, 1 times / day Route: ophthalmic Route: steady Dose: 0.05 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11952024/	healthy, 43 years Health Status: healthy Age Group: 43 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11952024/	Sources: https://pubmed.ncbi.nlm.nih.gov/11952024/
2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17229605/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/17229605/	Other AEs: Sleepiness... Other AEs: Sleepiness (7 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17229605/

AEs

AE	Significance	Dose	Population
Impaired driving ability	19 patients	4 mg 2 times / day steady, oral Studied dose Dose: 4 mg, 2 times / day Route: oral Route: steady Dose: 4 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11949773/	healthy, 21 - 45 years Health Status: healthy Age Group: 21 - 45 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11949773/
Sleepiness	7 patients	2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17229605/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/17229605/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197 CYP2E1 729

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://journals.sagepub.com/doi/abs/10.1177/026988110201600104?journalCode=jopa Page: 1.0	yes
CYP2E1 729	substrate 4014 Sources: https://journals.sagepub.com/doi/abs/10.1177/026988110201600104?journalCode=jopa Page: 1.0	yes
CYP3A4 1946	substrate 4014 Sources: https://journals.sagepub.com/doi/abs/10.1177/026988110201600104?journalCode=jopa Page: 1.0	yes	weak (co-administration study) Comment: Emedastine steady state pharmacokinetics were slightly altered as a result of the ketoconazole co-treatment. AUCss rose by about 33% and total clearance decreased by about 30% Sources: https://journals.sagepub.com/doi/abs/10.1177/026988110201600104?journalCode=jopa Page: 1.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4779	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4779
ChemicalBook	CB8728076	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8728076
MolPort	MolPort-006-167-701	https://www.molport.com/shop/molecule-link/MolPort-006-167-701
ZINC	ZINC000001530912	http://zinc15.docking.org/substances/ZINC000001530912

PubMed

Title	Date	PubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Contribution of mast cells to cerebral aneurysm formation.	2010-05	20334612
Chorea induced by antihistamine drugs.	2010-03-15	20108362
[Antihistamines in the treatment of allergic rhinitis--update 2008/2009].	2009-09	20564892
Emedastine difumarate: a review of its potential ameliorating effect for tissue remodeling in allergic diseases.	2009-08	19558341
Efficacy of olopatadine HCI 0.1%, ketotifen fumarate 0.025%, epinastine HCI 0.05%, emedastine 0.05% and fluorometholone acetate 0.1% ophthalmic solutions for seasonal allergic conjunctivitis: a placebo-controlled environmental trial.	2009-08	18631332
Psychoactive medication and traffic safety.	2009-03	19440432
(E)-1,1'-Bis[(E)-but-2-en-yl]-3,3'-(propane-1,3-di-yl)bis-(1H-benzimidazol-3-ium) dibromide monohydrate.	2008-10-18	21580997
Comparative efficacy of topical antihistamines in an animal model of early phase allergic conjunctivitis.	2008-05	18378229
Emedastine difumarate inhibits histamine-induced collagen synthesis in dermal fibroblasts.	2008	18714531
High-performance liquid chromatography-electrospray ionization-mass spectrometric determination of emedastine difumarate in human plasma and its pharmacokinetics.	2007-03	17462131
[The prompt effect of emedastine eye drop and the safety of its permanent use in children suffering from acute seasonal allergic conjunctivitis].	2007-02-11	17344175
Emedastine difumarate versus loratadine in chronic idiopathic urticaria: a randomized, double-blind, controlled European multicentre clinical trial.	2006-06-27	17229605
Estimation of in vivo percutaneous absorption of emedastine from bile excretion data using a deconvolution method.	2005-10	16272750
Biopharmaceutical considerations on antihistamine effects of topically administered emedastine.	2005-01	15761926
Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis.	2005	15631542
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.	2004-03	15049392
[Topical H1 antihistaminics in the therapy of acute conjunctival allergic reactions].	2004-01	15011308
Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus cetirizine in the treatment of seasonal allergic rhinitis.	2004	15553106
Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus terfenadine in the treatment of seasonal allergic rhinitis.	2004	15553105
Interactions of olopatadine and selected antihistamines with model and natural membranes.	2003-12	14704897
Suplatast tosilate inhibits eosinophil production and recruitment into the skin in murine contact sensitivity.	2003-09	14499249
Evaluation of the efficacy of antihistamines using human monocyte-derived dendritic cells stimulated with histamine.	2003-08	12894071
Development of a new dissolution test method for an oral controlled release preparation, the PVA swelling controlled release system (SCRS).	2003-06-05	12767711
[Effects of emedastine eyedrops on acute seasonal allergic conjunctivitis in children].	2003-04-06	12795028
Search of antimicrobial activity of selected non-antibiotic drugs.	2003-04-03	12669766
[In vitro effects of antiallergic eyedrops on complement activation induced by particulate matter].	2003-04	12843888
The effect of ketotifen on inflammatory markers in allergic conjunctivitis: an open, uncontrolled study.	2003-01-06	12515585
Onset and duration of action of ketotifen 0.025% and emedastine 0.05% in seasonal allergic conjunctivitis : efficacy after repeated pollen challenges in the vienna challenge chamber.	2003	17535045
Acute allergy reaction after posterior sub-Tenon's triamcinolone injection in the treatment of intermediate uveitis in the asthmatic patient.	2003	15314977
Comparison of emedastine 0.05% or nedocromil sodium 2% eye drops and placebo in controlling local reactions in subjects with allergic conjunctivitis.	2002-09-11	12219994
Histamine-induced cytokine production and ICAM-1 expression in human conjunctival fibroblasts.	2002-09	12607189
Pharmacokinetic and mass balance study of unlabelled and (14)C-labelled emedastine difumarate in healthy volunteers.	2002-09	12396273
A randomized, double-blind, placebo-controlled comparison of emedastine 0.05% ophthalmic solution with loratadine 10 mg and their combination in the human conjunctival allergen challenge model.	2002-03	11952027
Randomized, double-masked, placebo-controlled comparison of the efficacy of emedastine difumarate 0.05% ophthalmic solution and ketotifen fumarate 0.025% ophthalmic solution in the human conjunctival allergen challenge model.	2002-03	11952024
Effects of emedastine and cetirizine, alone and with alcohol, on actual driving of males and females.	2002-03	11949773
Effect of antiallergic drugs on interleukin 5-induced eosinophil infiltration of rat airways.	2002-03	11913525
Histamine-induced IL-6 and IL-8 production are differentially modulated by IFN-gamma and IL-4 in human keratinocytes.	2002-01	11916128
Clinical evaluation of twice-daily emedastine 0.05% eye drops (Emadine eye drops) versus levocabastine 0.05% eye drops in patients with allergic conjunctivitis.	2001-06	11384563
VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities.	2001-05	11430473
Emedastine and allergic conjunctivitis: new preparation. Poor assessment.	2001-04	11718155
Epinastine inhibits eosinophil chemotaxis and adhesion molecules in atopic dermatitis.	2001-03-19	14528065
Emedastine-ketoconazole: pharmacokinetic and pharmacodynamic interactions in healthy volunteers.	2001-03	11396749
Pharmacokinetics of emedastine difumarate, a new anti-histaminic agent in patients with renal impairment.	2001-03	11317479
Effect of emedastine difumarate on CC chemokine-elicited eosinophil migration.	2001	11408768
Cost effectiveness of emedastine versus levocabastine in the treatment of allergic conjunctivitis in 7 European countries.	2001	11303414
General pharmacology of 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarate. 1st communication: effects on the central nervous system.	1988-01	2896509
Pharmacologic analysis of LY188695 (KB-2413), 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)-benzimidazole difumarate, a potent histamine1 receptor antagonist.	1987-02	2883850

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose is one drop (0.05% solution) in the effected eye up to four times daily.

Route of Administration: Other

In Vitro Use Guide

Human trabecular meshwork cells were treated with emedastine and at concentration of 1.44 nM the drug antagonized histamine-induced phosphoinositide turnover by 50%.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:04:24 GMT 2025` Edited by `admin` on `Mon Mar 31 20:04:24 GMT 2025`
Record UNII	1P089Y932J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EMEDASTINE MONOFUMARATE

Common Name

English

1H-BENZIMIDAZOLE, 1-(2-ETHOXYETHYL)-2-(HEXAHYDRO-4-METHYL-1H-1,4-DIAZEPIN-1-YL)-, (2E)-2-BUTENEDIOATE (1:1)

Preferred Name

English

Code System Code Type Description

PUBCHEM

21893787