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

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
Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers.
1990 Dec
Antihistamines in late-phase clinical development for allergic disease.
2002 Feb
The effects of certain H(1)-antagonists on visual evoked potential in rats.
2003 Aug 30
Effects of second-generation histamine H1 receptor antagonists on the active avoidance response in rats.
2003 Jan-Feb
On the mechanisms underlying histamine induction of gastric mucosal lesions in rats with partial gastric vascular occlusion.
2003 Jun
Characteristics of the antihistamine effect of TAK-427, a novel imidazopyridazine derivative.
2003 May
A new histamine measurement system employing a confocal laser microscope and cultured human dermal microvascular endothelial cells.
2003 Sep
Efficacy and tolerability of ophthalmic epinastine assessed using the conjunctival antigen challenge model in patients with a history of allergic conjunctivitis.
2004 Jan
Influx and efflux transport of H1-antagonist epinastine across the blood-brain barrier.
2004 May
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
Population pharmacokinetics of epinastine, a histamine H1 receptor antagonist, in adults and children.
2005 Jan
Histamine receptors and the conjunctiva.
2005 Oct
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
[Pharmacological and clinical profile of epinastine hydrochloride (Alesion Dry Syrup 1%)].
2006 Jan
[Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis].
2006 May
Roles of octopaminergic and dopaminergic neurons in mediating reward and punishment signals in insect visual learning.
2006 Oct
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
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
Inhibitory effects of epinastine on chemokine production and MHC class II/CD54 expression in keratinocytes.
2007 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
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
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
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
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
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
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
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
Epinastine: topical ophthalmic second generation antihistamine without significant systemic side effects.
2009 Sep
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 00:54:11 UTC 2021
Edited
by admin
on Sat Jun 26 00:54:11 UTC 2021
Record UNII
Q13WX941EF
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
Epinastine is mainly excreted unchanged. About 55% of an intravenous dose is recovered unchanged in the urine with about 30% in feces.
FECAL
EXCRETED UNCHANGED
Epinastine is mainly excreted unchanged. About 55% of an intravenous dose is recovered unchanged in the urine with about 30% in feces.
URINE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MINOR
SALT/SOLVATE -> PARENT
TARGET->ANTAGONIST
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC SINGLE DOSE

Biological Half-life PHARMACOKINETIC SINGLE DOSE