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
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)
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 Date1.0662624E12 |
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 |
---|---|---|---|
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
R06AX24
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NDF-RT |
N0000000122
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NDF-RT |
N0000000190
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NCI_THESAURUS |
C29578
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NDF-RT |
N0000175883
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WHO-VATC |
QR06AX24
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NDF-RT |
N0000175519
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NDF-RT |
N0000175628
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WHO-ATC |
S01GX10
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WHO-VATC |
QS01GX10
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39684
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7176
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5953
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1027
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134507-59-8
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CHEMBL1106
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SUB06567MIG
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3241
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C053090
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C65515
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M4943
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Q13WX941EF
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80012-43-7
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EPINASTINE
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80012-43-7
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DB00751
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Epinastine
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PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)