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Details

Stereochemistry RACEMIC
Molecular Formula C16H15N3.BrH
Molecular Weight 330.2225
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPINASTINE HYDROBROMIDE

SMILES

c1ccc2c(c1)Cc3ccccc3N4C2CNC4=N.Br

InChI

InChIKey=ADPMHRDERZTFIN-UHFFFAOYSA-N
InChI=1S/C16H15N3.BrH/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 C16H15N3
Molecular Weight 249.311
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers.
1990 Dec
Epinastine ophthalmic solution (Elestat).
2004 Apr 26
Epinastine hydrochloride for atopic disease.
2004 Aug
Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis.
2005
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
Population pharmacokinetics of epinastine, a histamine H1 receptor antagonist, in adults and children.
2005 Jan
Histamine receptors and the conjunctiva.
2005 Oct
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
Epinastine in the management of ocular allergic disease.
2006 Fall
[Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis].
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
Expanding the neuron's calcium signaling repertoire: intracellular calcium release via voltage-induced PLC and IP3R activation.
2007 Apr
Duration of action of topical antiallergy drugs in a Guinea pig model of histamine-induced conjunctival vascular permeability.
2007 Aug
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
Simultaneous multiresponse optimization applied to epinastine determination in human serum by using capillary electrophoresis.
2007 Jul 9
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
Effects of sedative and non-sedative H1 antagonists on cognitive tasks: behavioral and near-infrared spectroscopy (NIRS) examinations.
2007 Sep
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
Development and characterisation of a novel and rapid lung eosinophil influx model in the rat.
2008 Aug
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
Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization.
2008 May
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
Epinastine 0.05% ophthalmic solution in contact lens-wearing subjects with a history of allergic conjunctivitis.
2009 Jan
Octopamine and tyramine modulate pheromone-sensitive olfactory sensilla of the hawkmoth Manduca sexta in a time-dependent manner.
2009 Jun
The role of dopamine in Drosophila larval classical olfactory conditioning.
2009 Jun 12
Differential effects of octopamine and tyramine on the central pattern generator for Manduca flight.
2009 Mar
Effects of sedative and nonsedative antihistamines on prefrontal activity during verbal fluency task in young children: a near-infrared spectroscopy (NIRS) study.
2009 Nov
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:36:24 UTC 2021
Edited
by admin
on Sat Jun 26 16:36:24 UTC 2021
Record UNII
4O6LIW7G3N
Record Status Validated (UNII)
Record Version
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Name Type Language
EPINASTINE HYDROBROMIDE
MI  
Common Name English
1H-DIBENZ(C,F)IMIDAZO(1,5-A)AZEPIN-3-AMINE, 9,13B-DIHYDRO-, HYDROBROMIDE (1:1)
Systematic Name English
EPINASTINE MONOHYDROBROMIDE
Common Name English
1H-DIBENZ(C,F)IMIDAZO(1,5-A)AZEPIN-3-AMINE, 9,13B-DIHYDRO-, MONOHYDROBROMIDE
Common Name English
EPINASTINE HYDROBROMIDE [MI]
Common Name English
Code System Code Type Description
CAS
80012-42-6
Created by admin on Sat Jun 26 16:36:24 UTC 2021 , Edited by admin on Sat Jun 26 16:36:24 UTC 2021
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
3061907
Created by admin on Sat Jun 26 16:36:24 UTC 2021 , Edited by admin on Sat Jun 26 16:36:24 UTC 2021
PRIMARY
CAS
127786-29-2
Created by admin on Sat Jun 26 16:36:24 UTC 2021 , Edited by admin on Sat Jun 26 16:36:24 UTC 2021
PRIMARY
MERCK INDEX
M4943
Created by admin on Sat Jun 26 16:36:24 UTC 2021 , Edited by admin on Sat Jun 26 16:36:24 UTC 2021
PRIMARY Merck Index
FDA UNII
4O6LIW7G3N
Created by admin on Sat Jun 26 16:36:24 UTC 2021 , Edited by admin on Sat Jun 26 16:36:24 UTC 2021
PRIMARY
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