U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H15N3.ClH
Molecular Weight 285.7719
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPINASTINE HYDROCHLORIDE

SMILES

c1ccc2c(c1)Cc3ccccc3N4C2CNC4=N.Cl

InChI

InChIKey=VKXSGUIOOQPGAF-UHFFFAOYSA-N
InChI=1S/C16H15N3.ClH/c17-16-18-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)19(15)16;/h1-8,15H,9-10H2,(H2,17,18);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H15N3
Molecular Weight 249.311
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Epinastine (brand names Alesion, Elestat, Purivist, Relestat) is a second-generation antihistamine and mast cell stabilizer. Epinastine is a topically active, direct H1-receptor antagonist and an inhibitor of the release of histamine from the mast cell. Epinastine is selective for the histamine H1-receptor and has affinity for the histamine H2 receptor. Epinastine also possesses affinity for the α1-, α2-, and 5-HT2 –receptors. Epinastine does not penetrate the blood/brain barrier and, therefore, is not expected to induce side effects of the central nervous system. Elestat ophthalmic solution is indicated for the prevention of itching associated with allergic conjunctivitis.

CNS Activity

Curator's Comment:: Epinastine does not penetrate the blood/brain barrier and, therefore, is not expected to induce side effects of the central nervous system.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ELESTAT

Approved Use

Epinastine HCl ophthalmic solution is indicated for the prevention of itching associated with allergic conjunctivitis. Epinastine HCl ophthalmic solution is an H1 histamine receptor antagonist indicated for the prevention of itching associated with allergic conjunctivitis. (1)

Launch Date

1.0662624E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.042 ng/mL
0.05 % 2 times / day multiple, ocular
dose: 0.05 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.025 ng/mL
0.05 % single, ocular
dose: 0.05 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
14.82 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
15.69 ng/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EPINASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
15.5 ng/mL
20.6 mg single, oral
dose: 20.6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.347 ng × h/mL
0.05 % 2 times / day multiple, ocular
dose: 0.05 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.465 ng × h/mL
0.05 % single, ocular
dose: 0.05 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
144.88 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
157.38 ng × h/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EPINASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.9 h
0.05 % 2 times / day multiple, ocular
dose: 0.05 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9.26 h
0.05 % single, ocular
dose: 0.05 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7.08 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPINASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.35 h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EPINASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
35.8%
single, oral
EPINASTINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
unhealthy, 33.8
n = 50
Health Status: unhealthy
Condition: Allergic Conjunctivitis
Age Group: 33.8
Sex: M+F
Population Size: 50
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as victimTox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine.
1990 Apr
Suppressive activity of epinastine hydrochloride on TARC production from human peripheral blood CD4+ T cells in-vitro.
2005 Aug
Effects of first- and second-generation histamine-H1-receptor antagonists on the pentobarbital-induced loss of the righting reflex in streptozotocin-induced diabetic mice.
2005 Feb
Octopamine and experience-dependent modulation of aggression in crickets.
2005 Feb 9
Exacerbation of palmoplantar pustulosis by granulocyte colony-stimulating factor.
2005 Jun
The various effects of four H1-antagonists on serum substance P levels in patients with atopic dermatitis.
2005 Oct
Histamine receptors and the conjunctiva.
2005 Oct
Participation of octopaminergic reward system and dopaminergic punishment system in insect olfactory learning revealed by pharmacological study.
2005 Sep
Epinastine hydrochloride antagonism against interleukin-4-mediated T cell cytokine imbalance in vitro.
2006
Effect of topical ophthalmic epinastine and olopatadine on tear volume in mice.
2006 Dec
Octopamine boosts snail locomotion: behavioural and cellular analysis.
2006 Dec
Elestat (epinastine HCl ophthalmic solution 0.05%) as a therapeutic for allergic conjunctivitis.
2006 Fall
Epinastine in the management of ocular allergic disease.
2006 Fall
Effects of histamine H(1) receptor antagonists on depressive-like behavior in diabetic mice.
2006 Feb
Role of substance P in allergic nasal symptoms in rats.
2006 Feb 17
[Pharmacological and clinical profile of epinastine hydrochloride (Alesion Dry Syrup 1%)].
2006 Jan
Parental use of the term "Hot Qi" to describe symptoms in their children in Hong Kong: a cross sectional survey "Hot Qi" in children.
2006 Jan 5
[Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis].
2006 May
Nasal congestion model in Brown Norway rats and the effects of some H1-antagonists.
2006 May
Octopamine mediates thermal preconditioning of the locust ventilatory central pattern generator via a cAMP/protein kinase A signaling pathway.
2006 Nov 22
Efficacy and response with olopatadine versus epinastine in ocular allergic symptoms: a post hoc analysis of data from a conjunctival allergen challenge study.
2006 Oct
Roles of octopaminergic and dopaminergic neurons in mediating reward and punishment signals in insect visual learning.
2006 Oct
Antiallergic drugs, azelastine hydrochloride and epinastine hydrochloride, inhibit ongoing IgE secretion of rat IgE-producing hybridoma FE-3 cells.
2006 Oct 10
Inhibition of the antigen provoked nasal reaction by second-generation antihistamines in patients with Japanese cedar pollinosis.
2006 Sep
An open-label, investigator-masked, crossover study of the ocular drying effects of two antihistamines, topical epinastine and systemic loratadine, in adult volunteers with seasonal allergic conjunctivitis.
2007 Apr
Expanding the neuron's calcium signaling repertoire: intracellular calcium release via voltage-induced PLC and IP3R activation.
2007 Apr
Effect of topical olopatadine and epinastine in the botulinum toxin B-induced mouse model of dry eye.
2007 Feb
Influences of octopamine and juvenile hormone on locomotor behavior and period gene expression in the honeybee, Apis mellifera.
2007 Feb
Inhibitory effects of epinastine on chemokine production and MHC class II/CD54 expression in keratinocytes.
2007 Feb
Distribution to the skin of epinastine hydrochloride in atopic dermatitis patients.
2007 Jan-Feb
Inhibition of IgE-mediated phosphorylation of FcepsilonRIgamma protein by antiallergic drugs in rat basophilic leukemia (RBL-2H3) cells: a novel action of antiallergic drugs.
2007 Jul
Efficacy and comfort of olopatadine 0.2% versus epinastine 0.05% ophthalmic solution for treating itching and redness induced by conjunctival allergen challenge.
2007 Jun
Development of new atopic dermatitis models characterized by not only itching but also inflammatory skin in mice.
2007 Jun 22
Influences of histamine H1 receptor antagonists on maximal electroshock seizure in infant rats.
2007 Mar
Aversive learning in honeybees revealed by the olfactory conditioning of the sting extension reflex.
2007 Mar 14
Ocular anti-allergic compounds selectively inhibit human mast cell cytokines in vitro and conjunctival cell infiltration in vivo.
2007 Nov
Inhibition of angiogenic factor production from murine mast cells by an antiallergic agent (epinastine hydrochloride) in vitro.
2008
Analysis of disease-dependent sedative profiles of H(1)-antihistamines by large-scale surveillance using the visual analog scale.
2008 Apr
Arousal facilitates collision avoidance mediated by a looming sensitive visual neuron in a flying locust.
2008 Aug
Repeated pre-treatment with antihistamines suppresses [corrected] transcriptional up-regulations of histamine H(1) receptor and interleukin-4 genes in toluene-2,4-diisocyanate-sensitized rats.
2008 Dec
Suppressive activity of epinastine hydrochloride on eosinophil activation in vitro.
2008 Jan-Feb
Ocular comfort and drying effects of three topical antihistamine/mast cell stabilizers in adults with allergic conjunctivitis: a randomized, double-masked crossover study.
2008 Jul
Modulation of eosinophil survival by epinastine hydrochloride, an H1 receptor antagonist, in vitro.
2008 Nov-Dec
Regulatory effects of antihistamines on the responses to staphylococcal enterotoxin B of human monocyte-derived dendritic cells and CD4+ T cells.
2008 Oct
Treatment of allergic conjunctivitis with olopatadine hydrochloride eye drops.
2008 Sep
Management of allergic conjunctivitis: an evaluation of the perceived comfort and therapeutic efficacy of olopatadine 0.2% and azelastine 0.05% from two prospective studies.
2009
Influence of epinastine hydrochloride, an H1-receptor antagonist, on the function of mite allergen-pulsed murine bone marrow-derived dendritic cells in vitro and in vivo.
2009
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 Aug
Suppression of histamine- and allergen-induced skin reactions: comparison of first- and second-generation antihistamines.
2009 Jun
Effects of sedative and nonsedative antihistamines on prefrontal activity during verbal fluency task in young children: a near-infrared spectroscopy (NIRS) study.
2009 Nov
Patents

Sample Use Guides

The recommended dosage is one drop in each eye twice a day. Treatment should be continued throughout the period of exposure (i.e., until the pollen season is over or until exposure to the offending allergen is terminated), even when symptoms are absent.
Route of Administration: Topical
Nasal epithelial cells (NECs) were stimulated with 25 ng/ml TNF-alpha in the presence of Epinastine (10 to 30 ng/ml). The minimum concentration of Epinastine (EP) that caused a significant decrease in eosinophil survival was 25 ng/ml. The addition of EP into eosinophil cultures did not cause inhibition of eosinophil survival, which was prolonged by stimulation with granulocyte-macrophage colony-stimulating factor (GM-CSF), even when 40 ng/ml EP was added to cell cultures.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:09:47 UTC 2021
Edited
by admin
on Fri Jun 25 21:09:47 UTC 2021
Record UNII
GFM415S5XL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPINASTINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   WHO-DD  
Common Name English
DE-114
Code English
EPINASTINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
1H-DIBENZ(C,F)IMIDAZO(1,5-A)AZEPIN-3-AMINE, 9,13B-DIHYDRO-, HYDROCHLORIDE (1:1)
Systematic Name English
WAL-802-CL
Code English
3-AMINO-9,13B-DIHYDRO-1H-DIBENZ(C,F)IMIDAZO(1,5-A)AZEPINE HYDROCHLORIDE, DL-
Common Name English
EPINASTINE HYDROCHLORIDE [WHO-DD]
Common Name English
ALESION
Brand Name English
EPINASTINE HYDROCHLORIDE [JAN]
Common Name English
EPINASTINE HYDROCHLORIDE [MI]
Common Name English
WAL 801 CL
Code English
ELESTAT
Brand Name English
EPINASTINE HYDROCHLORIDE [USP-RS]
Common Name English
WAL-801CL
Code English
EPINASTINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
EPINASTINE HCL
Common Name English
EPINASTINE HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
Code System Code Type Description
FDA UNII
GFM415S5XL
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
DRUG BANK
DBSALT000961
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
RXCUI
236961
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY RxNorm
EVMPD
SUB01910MIG
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
CAS
956316-28-2
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
NON-SPECIFIC STOICHIOMETRY
MERCK INDEX
M4943
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1236889
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY USP-RS
PUBCHEM
157313
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
MESH
C053090
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL1106
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
CAS
80012-44-8
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
SUPERSEDED
CAS
108929-04-0
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
EPA CompTox
108929-04-0
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
NCI_THESAURUS
C47512
Created by admin on Fri Jun 25 21:09:47 UTC 2021 , Edited by admin on Fri Jun 25 21:09:47 UTC 2021
PRIMARY
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BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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IMPURITY -> PARENT
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ACTIVE MOIETY