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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 of EMEDASTINE MONOFUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CCOCCN1C2=CC=CC=C2N=C1N3CCCN(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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35367
Gene ID: 3269.0
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
1.3 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2 ng/mL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
16.9 ng × h/mL
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.4 h
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
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
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
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

Doses

DosePopulationAdverse 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:
healthy, 21 - 45 years
n = 19
Health Status: healthy
Condition: lower respiratory tract infections or sexually transmitted infections
Age Group: 21 - 45 years
Sex: M+F
Population Size: 19
Sources:
Other AEs: Impaired driving ability...
Other AEs:
Impaired driving ability (19 patients)
Sources:
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:
healthy, 43 years
n = 14
Health Status: healthy
Condition: conjunctival allergen challenge model
Age Group: 43 years
Sex: M+F
Population Size: 14
Sources:
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:
unhealthy, adult
n = 192
Health Status: unhealthy
Condition: idiopathic chronic urticaria
Age Group: adult
Sex: unknown
Population Size: 192
Sources:
Other AEs: Sleepiness...
Other AEs:
Sleepiness (7 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
healthy, 21 - 45 years
n = 19
Health Status: healthy
Condition: lower respiratory tract infections or sexually transmitted infections
Age Group: 21 - 45 years
Sex: M+F
Population Size: 19
Sources:
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:
unhealthy, adult
n = 192
Health Status: unhealthy
Condition: idiopathic chronic urticaria
Age Group: adult
Sex: unknown
Population Size: 192
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
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%
Page: 1.0
PubMed

PubMed

TitleDatePubMed
Pharmacologic analysis of LY188695 (KB-2413), 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)-benzimidazole difumarate, a potent histamine1 receptor antagonist.
1987 Feb
Effect of emedastine difumarate on CC chemokine-elicited eosinophil migration.
2001
Cost effectiveness of emedastine versus levocabastine in the treatment of allergic conjunctivitis in 7 European countries.
2001
Emedastine and allergic conjunctivitis: new preparation. Poor assessment.
2001 Apr
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 Jun
Emedastine-ketoconazole: pharmacokinetic and pharmacodynamic interactions in healthy volunteers.
2001 Mar
Pharmacokinetics of emedastine difumarate, a new anti-histaminic agent in patients with renal impairment.
2001 Mar
VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities.
2001 May
Histamine-induced IL-6 and IL-8 production are differentially modulated by IFN-gamma and IL-4 in human keratinocytes.
2002 Jan
Comparison of emedastine 0.05% or nedocromil sodium 2% eye drops and placebo in controlling local reactions in subjects with allergic conjunctivitis.
2002 Jul-Aug
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 Mar
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 Mar
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Histamine-induced cytokine production and ICAM-1 expression in human conjunctival fibroblasts.
2002 Sep
Pharmacokinetic and mass balance study of unlabelled and (14)C-labelled emedastine difumarate in healthy volunteers.
2002 Sep
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
Acute allergy reaction after posterior sub-Tenon's triamcinolone injection in the treatment of intermediate uveitis in the asthmatic patient.
2003
[In vitro effects of antiallergic eyedrops on complement activation induced by particulate matter].
2003 Apr
[Effects of emedastine eyedrops on acute seasonal allergic conjunctivitis in children].
2003 Apr 6
Evaluation of the efficacy of antihistamines using human monocyte-derived dendritic cells stimulated with histamine.
2003 Aug
Interactions of olopatadine and selected antihistamines with model and natural membranes.
2003 Dec
The effect of ketotifen on inflammatory markers in allergic conjunctivitis: an open, uncontrolled study.
2003 Jan 6
Development of a new dissolution test method for an oral controlled release preparation, the PVA swelling controlled release system (SCRS).
2003 Jun 5
Epinastine inhibits eosinophil chemotaxis and adhesion molecules in atopic dermatitis.
2003 Nov-Dec
Suplatast tosilate inhibits eosinophil production and recruitment into the skin in murine contact sensitivity.
2003 Sep
Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus cetirizine in the treatment of seasonal allergic rhinitis.
2004
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.
2004 Mar
Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis.
2005
Biopharmaceutical considerations on antihistamine effects of topically administered emedastine.
2005 Jan
Estimation of in vivo percutaneous absorption of emedastine from bile excretion data using a deconvolution method.
2005 Oct
Emedastine difumarate versus loratadine in chronic idiopathic urticaria: a randomized, double-blind, controlled European multicentre clinical trial.
2006 Nov-Dec
[The prompt effect of emedastine eye drop and the safety of its permanent use in children suffering from acute seasonal allergic conjunctivitis].
2007 Feb 11
High-performance liquid chromatography-electrospray ionization-mass spectrometric determination of emedastine difumarate in human plasma and its pharmacokinetics.
2007 Mar
Emedastine difumarate inhibits histamine-induced collagen synthesis in dermal fibroblasts.
2008
Comparative efficacy of topical antihistamines in an animal model of early phase allergic conjunctivitis.
2008 May
(E)-1,1'-Bis[(E)-but-2-en-yl]-3,3'-(propane-1,3-di-yl)bis-(1H-benzimidazol-3-ium) dibromide monohydrate.
2008 Oct 18
Emedastine difumarate: a review of its potential ameliorating effect for tissue remodeling in allergic diseases.
2009 Aug
[Antihistamines in the treatment of allergic rhinitis--update 2008/2009].
2009 Sep
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Chorea induced by antihistamine drugs.
2010 Mar 15
Contribution of mast cells to cerebral aneurysm formation.
2010 May
Patents

Sample Use Guides

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 Fri Dec 15 20:11:21 GMT 2023
Edited
by admin
on Fri Dec 15 20:11:21 GMT 2023
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)
Systematic Name English
Code System Code Type Description
PUBCHEM
21893787
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
EVMPD
SUB25472
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
CAS
690625-90-2
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
SMS_ID
100000089499
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
FDA UNII
1P089Y932J
Created by admin on Fri Dec 15 20:11:22 GMT 2023 , Edited by admin on Fri Dec 15 20:11:22 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE