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

Details

Stereochemistry RACEMIC
Molecular Formula C16H15N3
Molecular Weight 249.311
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPINASTINE

SMILES

c1ccc2c(c1)Cc3ccccc3N4C2CNC4=N

InChI

InChIKey=WHWZLSFABNNENI-UHFFFAOYSA-N
InChI=1S/C16H15N3/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)

HIDE SMILES / InChI
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
Effects of cetirizine and epinastine on the skin response to histamine iontophoresis.
2001 Jan
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats.
2001 Jul
Pharmacokinetics of epinastine and a possible mechanism for double peaks in oral plasma concentration profiles.
2001 Jul
The role of central histaminergic neuron system as an anticonvulsive mechanism in developing brain.
2001 Nov
Preclinical comparison of ebastine and other second generation H1-antihistamines.
2001 Oct
Participation of chemical mediators other than histamine in nasal allergy signs: a study using mice lacking histamine H(1) receptors.
2002 Aug 9
Antihistamines in late-phase clinical development for allergic disease.
2002 Feb
Histamine H1 receptors are involved in mouse nasal allergic responses: a demonstration with H1 receptor-deficient mice.
2002 May
[Efficacy of combined drug therapy using a macrolide antibiotic and an antihistamine for adult patients with chronic paranasal sinusitis].
2003 Apr
A case of type IV solar urticaria identified by reverse in vitro serum test.
2003 Jul
Hygienic behavior in the honey bee (Apis mellifera L.) and the modulatory role of octopamine.
2003 Jun
A new histamine measurement system employing a confocal laser microscope and cultured human dermal microvascular endothelial cells.
2003 Sep
Antitussive effects of the H1-receptor antagonist epinastine in patients with atopic cough (eosinophilic bronchitis).
2004
Epinastine hydrochloride for atopic disease.
2004 Aug
Efficacy and tolerability of ophthalmic epinastine: a randomized, double-masked, parallel-group, active- and vehicle-controlled environmental trial in patients with seasonal allergic conjunctivitis.
2004 Jan
Effects of second-generation histamine H1 receptor antagonists on the sleep-wakefulness cycle in rats.
2004 Jun 28
Exacerbation of palmoplantar pustulosis by granulocyte colony-stimulating factor.
2005 Jun
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
Octopamine boosts snail locomotion: behavioural and cellular analysis.
2006 Dec
Epinastine in the management of ocular allergic disease.
2006 Fall
Role of substance P in allergic nasal symptoms in rats.
2006 Feb 17
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
Octopamine partially restores walking in hypokinetic cockroaches stung by the parasitoid wasp Ampulex compressa.
2007 Dec
Influences of octopamine and juvenile hormone on locomotor behavior and period gene expression in the honeybee, Apis mellifera.
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
Development and validation of liquid chromatographic and ultraviolet derivative spectrophotometric methods for determination of epinastine hydrochloride in coated tablets.
2007 Sep-Oct
Inhibition of angiogenic factor production from murine mast cells by an antiallergic agent (epinastine hydrochloride) in vitro.
2008
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
Roles of octopaminergic and dopaminergic neurons in appetitive and aversive memory recall in an insect.
2009 Aug 4
Epinastine 0.05% ophthalmic solution in contact lens-wearing subjects with a history of allergic conjunctivitis.
2009 Jan
Contrasting role of octopamine in appetitive and aversive learning in the crab Chasmagnathus.
2009 Jul 15
Suppression of histamine- and allergen-induced skin reactions: comparison of first- and second-generation antihistamines.
2009 Jun
The role of dopamine in Drosophila larval classical olfactory conditioning.
2009 Jun 12
Multiple action agents and the eye: do they really stabilize mast cells?
2009 Oct
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
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.
Name Type Language
EPINASTINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
EPINASTINE [MI]
Common Name English
3-AMINO-9,13B-DIHYDRO-1H-DIBENZ(C,F)IMIDAZO(1,5-A)AZEPINE
Common Name English
9,13B-DIHYDRO-1H-DIBENZ(C,F)IMIDAZO(1,5-A)AZEPIN-3-AMINE
Common Name English
WAL-801
Code English
PURIVIST
Brand Name English
EPINASTINE [VANDF]
Common Name English
EPINASTINE [INN]
Common Name English
(+/-)-EPINASTINE
Common Name English
1H-DIBENZ(C,F)IMIDAZO(1,5-A)AZEPIN-3-AMINE, 9,13B-DIHYDRO-
Systematic Name English
EPINASTINE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC R06AX24
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
NDF-RT N0000000122
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
NDF-RT N0000000190
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
NDF-RT N0000175883
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
WHO-VATC QR06AX24
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
NDF-RT N0000175519
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
NDF-RT N0000175628
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
WHO-ATC S01GX10
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
WHO-VATC QS01GX10
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
Code System Code Type Description
RXCUI
39684
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY RxNorm
IUPHAR
7176
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
INN
5953
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
DRUG CENTRAL
1027
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
CAS
134507-59-8
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
SUPERSEDED
ChEMBL
CHEMBL1106
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
EVMPD
SUB06567MIG
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
PUBCHEM
3241
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
MESH
C053090
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
NCI_THESAURUS
C65515
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
MERCK INDEX
M4943
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY Merck Index
FDA UNII
Q13WX941EF
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
CAS
80012-43-7
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
WIKIPEDIA
EPINASTINE
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
EPA CompTox
80012-43-7
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
DRUG BANK
DB00751
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY
LACTMED
Epinastine
Created by admin on Sat Jun 26 00:54:12 UTC 2021 , Edited by admin on Sat Jun 26 00:54:12 UTC 2021
PRIMARY