Epinastine

Identification

Summary

Epinastine is an H1 receptor antagonist used to prevent itching in allergic conjunctivitis.

Brand Names
Elestat
Generic Name
Epinastine
DrugBank Accession Number
DB00751
Background

Epinastine is used for the prevention of itching associated with allergic conjunctivitis. It has a multi-action effect that inhibits the allergic response in 3 ways: 1. stabilizes mast cells by preventing mast cell degranulation to control the allergic response, 2. prevents histamine binding to both the H1- and H2-receptors to stop itching and provide lasting protection, and 3. prevents the release of proinflammatory chemical mediators from the blood vessel to halt progression of the allergic response.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 249.3104
Monoisotopic: 249.126597495
Chemical Formula
C16H15N3
Synonyms
  • (±)-epinastine
  • 3-amino-9,13b-dihydro-1H-dibenz(c,f)imidazo(1,5-a)azepine
  • Epinastin
  • Epinastina
  • Epinastine
  • épinastine
  • Epinastinum
External IDs
  • WAL 801 Cl

Pharmacology

Indication

For the prevention of itching associated with allergic conjunctivitis.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Epinastine is an antihistamine and an inhibitor of histamine release from the mast cell for topical administration to the eyes. Epinastine is indicated for the prevention of itching associated with allergic conjunctivitis. 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 a1-, a2-, 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.

Mechanism of action

Epinastine has a multiaction effect that inhibits the allergic response in 3 ways: 1. stabilizes mast cells by preventing mast cell degranulation to control the allergic response, 2. prevents histamine binding to both the H1- and H2-receptors to stop itching and provide lasting protection, and 3. prevents the release of proinflammatory chemical mediators from the blood vessel to halt progression of the allergic response.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
AHistamine H2 receptor
antagonist
Humans
UAlpha-1A adrenergic receptor
unknown
Humans
UAlpha-2A adrenergic receptor
unknown
Humans
U5-hydroxytryptamine receptor 2A
antagonist
Humans
U5-hydroxytryptamine receptor 7
antagonist
Humans
Absorption

The absolute bioavailability of epinastine is about 40%.

Volume of distribution

Not Available

Protein binding

64%

Metabolism

Mainly excreted unchanged, less than 10% metabolized.

Route of elimination

Epinastine is mainly excreted unchanged. The renal elimination is mainly via active tubular secretion.

Half-life

12 hours

Clearance
  • 56 L/hr [patients with allergic conjunctivitis receiving one drop of ELESTAT® ophthalmic solution in each eye twice daily for seven days]
Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
PathwayCategory
Epinastine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Epinastine is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Epinastine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Epinastine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Epinastine can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Epinastine can be decreased when combined with Acebutolol.
AcenocoumarolThe risk or severity of adverse effects can be increased when Epinastine is combined with Acenocoumarol.
AcetaminophenThe metabolism of Epinastine can be decreased when combined with Acetaminophen.
AcetazolamideThe risk or severity of adverse effects can be increased when Epinastine is combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Epinastine is combined with Acetophenazine.
AclidiniumEpinastine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Epinastine hydrochlorideGFM415S5XL108929-04-0VKXSGUIOOQPGAF-UHFFFAOYSA-N
International/Other Brands
Alegain (Kyorin Rimedio) / Alenapion (Choseido Pharmaceutical) / Alesion (Boehringer Ingelheim) / Alesiotec (Nihon Yakuhin Kogyo) / Alket (Poen) / Allernothin (Morishita Jintan) / Allerstin (Dong Koo) / Alpeed (Daito) / Aplatin (Taiyo Pharmaceutical) / Aresten (Il Sung) / Asmot (Tatsumi Kagaku) / Atergit (Roemmers) / Azusaleon (Shiono Kemikaru) / Elpinan (Towa Yakuhin) / Epinazion (Medisa Shinyaku) / Epioftal (Farmindustria) / Flurinol (Boehringer Ingelheim) / Helvottz (Yoshindo) / Kai lai Zhi (Carelife Pharmaceutical Co Ltd) / Pinasion (Taisho Yakuhin) / Purivist (Allergan) / Relenastine (Lansier) / Relestat (Allergan) / Talerc (Aché) / Timkent (Nisshin Seiyaku) / Yupitel (Iwaki Seiyaku)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ElestatSolution / drops0.5 mg/1mLOphthalmicAllergan, Inc.2004-01-19Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EpinastineSolution / drops0.5 mg/1mLOphthalmicAkorn, Inc.2017-05-05Not applicableUS flag
Epinastine HClSolution0.5 mg/1mLOphthalmicAv Kare, Inc.2011-11-152015-02-20US flag
Epinastine HClSolution0.5 mg/1mLOphthalmicCypress Pharmaceuticals, Inc.2011-05-022013-09-11US flag
Epinastine HydrochlorideSolution / drops0.5 mg/1mLOphthalmicA-S Medication Solutions2013-11-052018-03-31US flag
Epinastine HydrochlorideSolution0.5 mg/1mLOphthalmicApotex Corp.2011-10-312021-03-01US flag
Epinastine HydrochlorideSolution / drops0.5 mg/1mLOphthalmicPaddock Laboratories, Inc.2011-11-012014-12-31US flag
Epinastine HydrochlorideSolution / drops0.5 mg/1mLOphthalmicBreckenridge Pharmaceutical, Inc.2013-11-05Not applicableUS flag
Epinastine HydrochlorideSolution0.5 mg/1mLOphthalmicSun Pharmaceutical Industries, Inc.2011-11-01Not applicableUS flag
Epinastine HydrochlorideSolution / drops0.5 mg/1mLOphthalmicSomerset Therapeutics, Llc2016-09-14Not applicableUS flag

Categories

ATC Codes
S01GX10 — EpinastineR06AX24 — Epinastine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Dibenzazepines
Direct Parent
Dibenzazepines
Alternative Parents
Azepines / Benzenoids / Imidazolines / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
2-imidazoline / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzenoid / Carboximidamide / Dibenzazepine / Guanidine / Hydrocarbon derivative / Organic 1,3-dipolar compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
guanidines, benzazepine (CHEBI:51032)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Q13WX941EF
CAS number
80012-43-7
InChI Key
WHWZLSFABNNENI-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2,4-diazatetracyclo[12.4.0.0²,⁶.0⁷,¹²]octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine
SMILES
NC1=NCC2N1C1=CC=CC=C1CC1=CC=CC=C21

References

Synthesis Reference

Akiharu Isowaki, Tomoko Nakajima, Akira Ohtori, "Percutaneously Absorptive Ophthalmic Preparation Comprising Epinastine." U.S. Patent US20090143359, issued June 04, 2009.

US20090143359
General References
  1. Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. [Article]
  2. Schilling JC, Adamus WS, Kuthan H: Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers. Int J Clin Pharmacol Ther Toxicol. 1990 Dec;28(12):493-7. [Article]
Human Metabolome Database
HMDB0014889
KEGG Drug
D01713
PubChem Compound
3241
PubChem Substance
46509056
ChemSpider
3128
BindingDB
50131441
RxNav
39684
ChEBI
51032
ChEMBL
CHEMBL1106
Therapeutic Targets Database
DAP001074
PharmGKB
PA164764489
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Epinastine
FDA label
Download (113 KB)
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHypersensitivity1
4CompletedTreatmentSeasonal Allergic Conjunctivitis2
4WithdrawnTreatmentSeasonal Allergic Conjunctivitis1
3CompletedNot AvailableSeasonal Allergic Conjunctivitis1
3CompletedTreatmentAtopic Dermatitis (AD)2
3CompletedTreatmentRhinitis, Allergic, Perennial2
3CompletedTreatmentSeasonal Allergic Rhinitis1
2CompletedTreatmentAllergic Rhinitis (AR)1
2CompletedTreatmentSeasonal Allergic Rhinitis1
1CompletedTreatmentHealthy Volunteers4

Pharmacoeconomics

Manufacturers
  • Allergan inc
Packagers
  • Allergan Inc.
Dosage Forms
FormRouteStrength
SolutionIntraocular; Ophthalmic0.5 mg
SolutionOphthalmic0.5 mg/1mL
Solution / dropsOphthalmic0.5 mg/1mL
SolutionOphthalmic0.5 mg
SyrupOral0.2 g
TabletOral10 mg
Tablet, extended releaseOral
Tablet, coatedOral20 mg
Solution / dropsConjunctival
LiquidOphthalmic0.5 mg/1ml
Solution / dropsOphthalmic
Prices
Unit descriptionCostUnit
Elestat 0.05% Solution 5ml Bottle116.58USD bottle
Elestat 0.05% eye drops22.94USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7429602No2008-09-302020-11-29US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)205-208 °CNot Available
logP3.51BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.163 mg/mLALOGPS
logP2.53ALOGPS
logP3.07ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.62 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity76.9 m3·mol-1ChemAxon
Polarizability27.33 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9923
Blood Brain Barrier+0.9787
Caco-2 permeable+0.5766
P-glycoprotein substrateSubstrate0.5665
P-glycoprotein inhibitor INon-inhibitor0.8193
P-glycoprotein inhibitor IINon-inhibitor0.5736
Renal organic cation transporterInhibitor0.7994
CYP450 2C9 substrateNon-substrate0.8676
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.5422
CYP450 1A2 substrateNon-inhibitor0.5686
CYP450 2C9 inhibitorNon-inhibitor0.9243
CYP450 2D6 inhibitorNon-inhibitor0.5228
CYP450 2C19 inhibitorNon-inhibitor0.8702
CYP450 3A4 inhibitorNon-inhibitor0.6566
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.726
Ames testAMES toxic0.5689
CarcinogenicityNon-carcinogens0.9144
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7509 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9353
hERG inhibition (predictor II)Non-inhibitor0.8419
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Tsujii T, Yamamoto E, Ohira T, Saito N, Watanabe S: Effects of sedative and non-sedative H1 antagonists on cognitive tasks: behavioral and near-infrared spectroscopy (NIRS) examinations. Psychopharmacology (Berl). 2007 Sep;194(1):83-91. Epub 2007 May 30. [Article]
  2. Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
Gene Name
HRH2
Uniprot ID
P25021
Uniprot Name
Histamine H2 receptor
Molecular Weight
40097.65 Da
References
  1. Bielory L, Ghafoor S: Histamine receptors and the conjunctiva. Curr Opin Allergy Clin Immunol. 2005 Oct;5(5):437-40. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Unknown
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Unknown
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Dupont LJ, Pype JL, Meade CJ, DeLeyn P, Deneffe G, Demedts MG, Verleden GM: Epinastine (WAL 801CL) inhibits the electrical field stimulation-induced cholinergic contraction in guinea pig and human airways in vitro. Eur Respir J. 1999 Nov;14(5):1068-75. [Article]
  2. Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR7
Uniprot ID
P34969
Uniprot Name
5-hydroxytryptamine receptor 7
Molecular Weight
53554.43 Da
References
  1. Dupont LJ, Pype JL, Meade CJ, DeLeyn P, Deneffe G, Demedts MG, Verleden GM: Epinastine (WAL 801CL) inhibits the electrical field stimulation-induced cholinergic contraction in guinea pig and human airways in vitro. Eur Respir J. 1999 Nov;14(5):1068-75. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Ishiguro N, Nozawa T, Tsujihata A, Saito A, Kishimoto W, Yokoyama K, Yotsumoto T, Sakai K, Igarashi T, Tamai I: Influx and efflux transport of H1-antagonist epinastine across the blood-brain barrier. Drug Metab Dispos. 2004 May;32(5):519-24. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 06, 2021 01:40