Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H15N3 |
Molecular Weight | 249.3104 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NCC2N1C3=C(CC4=C2C=CC=C4)C=CC=C3
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)
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 | ( + / - ) |
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 |
7.6 null [pIC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ELESTAT Approved UseEpinastine 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 Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
35.8% |
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: |
unhealthy, 33.8 n = 50 Health Status: unhealthy Condition: Allergic Conjunctivitis Age Group: 33.8 Sex: M+F Population Size: 50 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Simultaneous multiresponse optimization applied to epinastine determination in human serum by using capillary electrophoresis. | 2007 Jul 9 |
|
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 |
|
Ocular anti-allergic compounds selectively inhibit human mast cell cytokines in vitro and conjunctival cell infiltration in vivo. | 2007 Nov |
|
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 |
|
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 |
|
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 |
|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19180992
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
Edited
Fri Dec 15 15:59:41 GMT 2023
by
admin
on
Fri Dec 15 15:59:41 GMT 2023
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Record UNII |
Q13WX941EF
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
R06AX24
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NDF-RT |
N0000000122
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N0000000190
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NCI_THESAURUS |
C29578
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N0000175883
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QR06AX24
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N0000175519
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N0000175628
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S01GX10
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WHO-VATC |
QS01GX10
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39684
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EPINASTINE
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DB00751
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Epinastine
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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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
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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
|
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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SALT/SOLVATE -> PARENT | |||
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TARGET->ANTAGONIST |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Tmax | PHARMACOKINETIC |
|
SINGLE DOSE |
|
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Biological Half-life | PHARMACOKINETIC |
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SINGLE DOSE |
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