EMEDASTINE DIFUMARATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H26N4O.2C4H4O4
Molecular Weight	534.5589
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.CCOCCN1C2=CC=CC=C2N=C1N3CCCN(C)CC3

InChI

InChIKey=FWLKKPKZQYVAFR-LVEZLNDCSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H26N4O
Molecular Weight	302.4145
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

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

Description

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 315	Antagonist 2,778		1.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic conjunctivitis 100	Primary		Approved 8,429	EMADINE

C_max

Value	Dose	Analyte	Population
2 ng/mL	2 mg single, oral	EMEDASTINE plasma	Homo sapiens
2.9 ng/mL	2 mg single, oral	EMEDASTINE plasma	Homo sapiens
4 ng/mL	2 mg 2 times / day steady-state, oral	EMEDASTINE plasma	Homo sapiens
6 ng/mL	2 mg 2 times / day steady-state, oral	EMEDASTINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
16.9 ng × h/mL	2 mg single, oral	EMEDASTINE plasma	Homo sapiens
29.7 ng × h/mL	2 mg single, oral	EMEDASTINE plasma	Homo sapiens
24.4 ng × h/mL	2 mg 2 times / day steady-state, oral	EMEDASTINE plasma	Homo sapiens
46.4 ng × h/mL	2 mg 2 times / day steady-state, oral	EMEDASTINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
6.4 h	2 mg single, oral	EMEDASTINE plasma	Homo sapiens
10.1 h	2 mg single, oral	EMEDASTINE plasma	Homo sapiens
6.6 h	2 mg 2 times / day steady-state, oral	EMEDASTINE plasma	Homo sapiens
9.1 h	2 mg 2 times / day steady-state, oral	EMEDASTINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
4 mg 2 times / day steady, oral Studied dose	healthy, 21 - 45 years n = 19	Other AEs: Impaired driving ability...
0.05 % 1 times / day steady, ophthalmic Recommended	healthy, 43 years n = 14
2 mg 2 times / day steady, oral Recommended	unhealthy, adult n = 192	Other AEs: Sleepiness...

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AEs

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AE	Significance	Dose	Population
Impaired driving ability	19 patients	4 mg 2 times / day steady, oral Studied dose	healthy, 21 - 45 years n = 19
Sleepiness	7 patients	2 mg 2 times / day steady, oral Recommended	unhealthy, adult n = 192

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1,054 CYP2E1 667

Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP1A2 1,054	substrate 3,367	yes
CYP2E1 667	substrate 3,367	yes
CYP3A4 1,737	substrate 3,367	yes	weak (co-administration study)

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Pharmacologic analysis of LY188695 (KB-2413), 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)-benzimidazole difumarate, a potent histamine1 receptor antagonist.	1987 Feb	2883850
General pharmacology of 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarate. 1st communication: effects on the central nervous system.	1988 Jan	2896509
Emedastine and allergic conjunctivitis: new preparation. Poor assessment.	2001 Apr	11718155
VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities.	2001 May	11430473
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	11952024

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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%.