EMEDASTINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H26N4O
Molecular Weight	302.4145
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCOCCN1C(=NC2=C1C=CC=C2)N3CCCN(C)CC3

InChI

InChIKey=KBUZBQVCBVDWKX-UHFFFAOYSA-N

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

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

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 316	Antagonist 2,849		1.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic conjunctivitis 101	Primary		Approved 8,583	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

Show entries

Dose	Population	Adverse events
4 mg 2 times / day steady, oral Studied dose	healthy, 21 - 45 years	Other AEs: Impaired driving ability...
0.05 % 1 times / day steady, ophthalmic Recommended	healthy, 43 years
2 mg 2 times / day steady, oral Recommended	unhealthy, adult	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
Sleepiness	7 patients	2 mg 2 times / day steady, oral Recommended	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1,197 CYP2E1 729

Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP1A2 1,197	substrate 4,014	yes
CYP2E1 729	substrate 4,014	yes
CYP3A4 1,946	substrate 4,014	yes	weak (co-administration study)

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Sourcing

Sourcing

Show entries

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
Effect of emedastine difumarate on CC chemokine-elicited eosinophil migration.	2001	11408768
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	11384563
Emedastine-ketoconazole: pharmacokinetic and pharmacodynamic interactions in healthy volunteers.	2001 Mar	11396749

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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%.