EPINASTINE HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H15N3.ClH
Molecular Weight	285.771
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NC1=NCC2N1C3=CC=CC=C3CC4=CC=CC=C24

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	36.461
Charge	0
Count

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

Molecular Formula	C16H15N3
Molecular Weight	249.3104
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021565s005lbl.pdf | https://www.drugbank.ca/drugs/DB00751

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021565s005lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/18446005	Antagonist 2849		7.6 null [pIC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic conjunctivitis 101 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021565s005lbl.pdf	Primary		Approved 8583	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 2003

C_max

Value	Dose	Analyte	Population
14.82 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31947890	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31947890	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 REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf	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
0.025 ng/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf	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
0.042 ng/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf	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

AUC

Value	Dose	Analyte	Population
144.88 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31947890	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31947890	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
0.465 ng × h/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf	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
0.347 ng × h/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf	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

T_1/2

Value	Dose	Analyte	Population
7.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31947890	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31947890	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
9.26 h REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf	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
11.9 h REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
35.8% REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf	single, oral		EPINASTINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://clinicaltrials.gov/ct2/show/results/NCT02251613	unhealthy, 33.8 Health Status: unhealthy Age Group: 33.8 Sex: M+F Sources: https://clinicaltrials.gov/ct2/show/results/NCT02251613	Sources: https://clinicaltrials.gov/ct2/show/results/NCT02251613

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946		substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 776 CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2C19 1119 CYP2E1 729 CYP4A11 137

Drug as victim

Target	Modality	Activity
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=6 Page: 6,24	major
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=6 Page: 6,24	major
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=6 Page: 6,24	minor
CYP1A1 389	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=24 Page: 24.0	no
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=24 Page: 24.0	no
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=24 Page: 24.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=24 Page: 24.0	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=24 Page: 24.0	no
CYP4A11 137	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-565_Elestat_BioPharmr.pdf#page=24 Page: 24.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0014299999003751?via%3Dihub

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51032	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51032
ChemicalBook	CB2230197	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2230197
eMolecules	901834	https://www.emolecules.com/cgi-bin/more?vid=901834
MolPort	MolPort-005-935-541	https://www.molport.com/shop/molecule-link/MolPort-005-935-541

PubMed

Title	Date	PubMed
Effects of sedative and nonsedative antihistamines on prefrontal activity during verbal fluency task in young children: a near-infrared spectroscopy (NIRS) study.	2009-11	19705105
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009-10-02	19798416
Multiple action agents and the eye: do they really stabilize mast cells?	2009-10	19652595
Epinastine: topical ophthalmic second generation antihistamine without significant systemic side effects.	2009-09	19630694
Roles of octopaminergic and dopaminergic neurons in appetitive and aversive memory recall in an insect.	2009-08-04	19653886
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
Contrasting role of octopamine in appetitive and aversive learning in the crab Chasmagnathus.	2009-07-15	19603069
The role of dopamine in Drosophila larval classical olfactory conditioning.	2009-06-12	19521527
Suppression of histamine- and allergen-induced skin reactions: comparison of first- and second-generation antihistamines.	2009-06	19558008
Octopamine and tyramine modulate pheromone-sensitive olfactory sensilla of the hawkmoth Manduca sexta in a time-dependent manner.	2009-06	19301013
Differential effects of octopamine and tyramine on the central pattern generator for Manduca flight.	2009-03	19137318
Modulation of eosinophil survival by epinastine hydrochloride, an H1 receptor antagonist, in vitro.	2009-02-03	19180992
Epinastine 0.05% ophthalmic solution in contact lens-wearing subjects with a history of allergic conjunctivitis.	2009-01	19125045
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	19668586
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	19381339
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.	2008-12	19075512
Regulatory effects of antihistamines on the responses to staphylococcal enterotoxin B of human monocyte-derived dendritic cells and CD4+ T cells.	2008-10	18524543
Treatment of allergic conjunctivitis with olopatadine hydrochloride eye drops.	2008-09	19668750
Arousal facilitates collision avoidance mediated by a looming sensitive visual neuron in a flying locust.	2008-08	18509080
Development and characterisation of a novel and rapid lung eosinophil influx model in the rat.	2008-08	18490184
Ocular comfort and drying effects of three topical antihistamine/mast cell stabilizers in adults with allergic conjunctivitis: a randomized, double-masked crossover study.	2008-07	18691985
Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization.	2008-05	18446005
Suppressive activity of epinastine hydrochloride on eosinophil activation in vitro.	2008-04-10	18396776
Analysis of disease-dependent sedative profiles of H(1)-antihistamines by large-scale surveillance using the visual analog scale.	2008-04	18597008
Inhibition of angiogenic factor production from murine mast cells by an antiallergic agent (epinastine hydrochloride) in vitro.	2008	18725994
Octopamine partially restores walking in hypokinetic cockroaches stung by the parasitoid wasp Ampulex compressa.	2007-12	18055629
Ocular anti-allergic compounds selectively inhibit human mast cell cytokines in vitro and conjunctival cell infiltration in vivo.	2007-11	17877767
Development and validation of liquid chromatographic and ultraviolet derivative spectrophotometric methods for determination of epinastine hydrochloride in coated tablets.	2007-10-25	17955971
Effects of sedative and non-sedative H1 antagonists on cognitive tasks: behavioral and near-infrared spectroscopy (NIRS) examinations.	2007-09	17534605
Duration of action of topical antiallergy drugs in a Guinea pig model of histamine-induced conjunctival vascular permeability.	2007-08	17803429
Simultaneous multiresponse optimization applied to epinastine determination in human serum by using capillary electrophoresis.	2007-07-09	17606014
Inhibition of IgE-mediated phosphorylation of FcepsilonRIgamma protein by antiallergic drugs in rat basophilic leukemia (RBL-2H3) cells: a novel action of antiallergic drugs.	2007-07	17499203
Development of new atopic dermatitis models characterized by not only itching but also inflammatory skin in mice.	2007-06-22	17459367
Efficacy and comfort of olopatadine 0.2% versus epinastine 0.05% ophthalmic solution for treating itching and redness induced by conjunctival allergen challenge.	2007-06	17559743
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.	2007-04	17617284
Expanding the neuron's calcium signaling repertoire: intracellular calcium release via voltage-induced PLC and IP3R activation.	2007-04	17341135
Aversive learning in honeybees revealed by the olfactory conditioning of the sting extension reflex.	2007-03-14	17372627
Influences of histamine H1 receptor antagonists on maximal electroshock seizure in infant rats.	2007-03	17329841
Effect of topical olopatadine and epinastine in the botulinum toxin B-induced mouse model of dry eye.	2007-02	17341156
Influences of octopamine and juvenile hormone on locomotor behavior and period gene expression in the honeybee, Apis mellifera.	2007-02	17082965
Inhibitory effects of epinastine on chemokine production and MHC class II/CD54 expression in keratinocytes.	2007-02	17070018
Effect of topical ophthalmic epinastine and olopatadine on tear volume in mice.	2006-12	17099387
Octopamine boosts snail locomotion: behavioural and cellular analysis.	2006-12	17072577
Octopamine mediates thermal preconditioning of the locust ventilatory central pattern generator via a cAMP/protein kinase A signaling pathway.	2006-11-22	17122036
Distribution to the skin of epinastine hydrochloride in atopic dermatitis patients.	2006-10-14	17324825
Efficacy and response with olopatadine versus epinastine in ocular allergic symptoms: a post hoc analysis of data from a conjunctival allergen challenge study.	2006-10	17157118
Roles of octopaminergic and dopaminergic neurons in mediating reward and punishment signals in insect visual learning.	2006-10	17067299
Inhibition of the antigen provoked nasal reaction by second-generation antihistamines in patients with Japanese cedar pollinosis.	2006-09	17075266
Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers.	1990-12	1982280
New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine.	1990-04	1972625

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 18:22:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:46 GMT 2025`
Record UNII	GFM415S5XL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALESION

Preferred Name

English

EPINASTINE HYDROCHLORIDE

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 [JAN]

Common Name

English

EPINASTINE HYDROCHLORIDE [MI]

Common Name

English

WAL 801 CL

Code

English

Epinastine hydrochloride [WHO-DD]

Common Name

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