EBASTINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C32H39NO2
Molecular Weight	469.6588
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)c1ccc(cc1)C(=O)CCCN2CCC(CC2)OC(c3ccccc3)c4ccccc4

InChI

InChIKey=MJJALKDDGIKVBE-UHFFFAOYSA-N

InChI=1S/C32H39NO2/c1-32(2,3)28-18-16-25(17-19-28)30(34)15-10-22-33-23-20-29(21-24-33)35-31(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-9,11-14,16-19,29,31H,10,15,20-24H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C32H39NO2
Molecular Weight	469.6588
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340

Ebastine is an antihistamine which blocks H1-receptors through its carboxylic acid metabolite. Ebastine is indicated for the treatment of allergic rhinitis and chronic idiopathic urticaria.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 304 Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340	Antagonist 2575

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 96 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340	Primary		Approved 8043	EBATROL Approved Use Unknown
Chronic idiopathic urticaria 10 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340	Primary		Approved 8043	EBATROL Approved Use Unknown

PubMed

Title	Date	PubMed
The non-cardiac systemic side-effects of antihistamines: ebastine.	1999 Jul	10444230
[The effect of second generation histamine antagonists on the heart].	2001	11575008
Safety of antihistamines in children.	2001	11235817
Problems of heart rate correction in assessment of drug-induced QT interval prolongation.	2001 Apr	11332559
Effects of supratherapeutic doses of ebastine and terfenadine on the QT interval.	2001 Aug	11488779
A novel cytochrome P450 enzyme responsible for the metabolism of ebastine in monkey small intestine.	2001 Jun	11353747
Effect of age and gender on the pharmacokinetics of ebastine after single and repeated dosing in healthy subjects.	2001 Mar	11396753
Azelastine tablets in the treatment of chronic idiopathic urticaria. Phase iii, randomised, double-blind, placebo and active controlled multicentric clinical trial.	2001 Mar-Apr	11316966
Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-chlorpheniramine, a classical antihistamine.	2001 Nov	11736858
Urticaria to cetirizine.	2002	12371532
Anaphylactoid reaction caused by moxifloxacin.	2002	12109537
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].	2002	11980129
In vivo evidence for a lack of central effect of ebastine, an antihistaminic agent, in rats: a microdialysis study.	2002 Dec	12501012
Comparative pharmacology of H1 antihistamines: clinical relevance.	2002 Dec 16	12517581
A double-blind, randomized, single-dose, crossover comparison of levocetirizine with ebastine, fexofenadine, loratadine, mizolastine, and placebo: suppression of histamine-induced wheal-and-flare response during 24 hours in healthy male subjects.	2002 Feb	11868924
Cardiotoxicity of new antihistamines and cisapride.	2002 Feb 28	12052668
Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes.	2002 Jan	11752129
Differential cognitive effects of ebastine and (+)-chlorpheniramine in healthy subjects: correlation between cognitive impairment and plasma drug concentration.	2002 Mar	11874393
Involvement of CYP2J2 on the intestinal first-pass metabolism of antihistamine drug, astemizole.	2002 Nov	12386130
Efficacy of ebastine, cetirizine, and loratadine in histamine cutaneous challenges.	2002 Sep	12269645
Chronic urticaria: a role for newer immunomodulatory drugs?	2003	12688835
In vitro inhibition of human small intestinal and liver microsomal astemizole O-demethylation: different contribution of CYP2J2 in the small intestine and liver.	2003 Jun	12851038
Efficacy of ebastine in the control of nasal congestion associated with allergic rhinitis.	2003 Mar	12731456
Effects of second generation of histamine H1 antagonists, cetirizine and ebastine, on the antitussive and rewarding effects of dihydrocodeine in mice.	2003 Mar	12536265
[In seasonal and perennial rhinitis. Superiority to standard H1 blockers].	2003 May 29	12866281
[Antihistaminics. Side effects also after raising dosage at the placebo level].	2003 May 29	12866280
Fixed drug eruption due to loratadine.	2003 Sep-Oct	14572420
A randomized, double-blind, placebo-controlled study comparing the efficacy and safety of ebastine (20 mg and 10 mg) to loratadine 10 mg once daily in the treatment of seasonal allergic rhinitis.	2004	15160443
Cetirizine: a review of its use in allergic disorders.	2004	14977391
Expression of CYP4F12 in gastrointestinal and urogenital epithelia.	2004 Apr	15078342
Efficacy and safety of ebastine 20 mg compared to loratadine 10 mg once daily in the treatment of seasonal allergic rhinitis: a randomized, double-blind, placebo-controlled study.	2004 Apr	15031611
A review of the second-generation antihistamine ebastine for the treatment of allergic disorders.	2004 Aug	15264995
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.	2004 Jul	15180765
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.	2004 Mar	15049392
Meta-analysis of the efficacy of ebastine 20 mg compared to loratadine 10 mg and placebo in the symptomatic treatment of seasonal allergic rhinitis.	2005 Dec	16224195
The effect of CYP2J2, CYP3A4, CYP3A5 and the MDR1 polymorphisms and gender on the urinary excretion of the metabolites of the H-receptor antihistamine ebastine: a pilot study.	2006 Aug	16842392
[Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis].	2006 May	16883093
Acceptance survey of a fast dissolving tablet pharmaceutical formulation in allergic patients. Satisfaction and expectancies.	2006 May-Jun	16750120
Characterization of ebastine, hydroxyebastine, and carebastine metabolism by human liver microsomes and expressed cytochrome P450 enzymes: major roles for CYP2J2 and CYP3A.	2006 Nov	16896065
Comparison of inhibition of cutaneous histamine reaction of ebastine fast-dissolving tablet [20 mg] versus desloratadine capsule [5 mg]: a randomized, double-blind, double-dummy, placebo-controlled, three-period crossover study in healthy, nonatopic adults.	2007 Dec	18201596
Rupatadine in allergic rhinitis and chronic urticaria.	2008 Apr	18339040
Granular parakeratosis presenting with facial keratotic papules.	2008 Jan-Feb	18187827
Probing ligand binding modes of human cytochrome P450 2J2 by homology modeling, molecular dynamics simulation, and flexible molecular docking.	2008 May 1	18004755
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS).	2008 Sep	18566547

Patents

Sample Use Guides

In Vivo Use Guide

Once-daily, 10 mg.

Route of Administration: Oral

In Vitro Use Guide

In vitro, ebastine and carebastine were shown to block the release of anti-IgE-induced eicosanoids LTC4/D4 and PGD2. Ebastine inhibited release of the two mediators by 30% at clinically relevant concentrations (IC30 = 2.57–9.6 umol/L).

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:10:11 UTC 2021` Edited by `admin` on `Fri Jun 25 21:10:11 UTC 2021`
Record UNII	TQD7Q784P1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EBASTINE

Official Name

English

RP-64305

Code

English

EBASTINE [EP MONOGRAPH]

Common Name

English

EBASTINE [WHO-DD]

Common Name

English

RP 64305

Code

English

LAS-W-090

Code

English

EBASTINE [MART.]

Common Name

English

EBASTINE [USAN]

Common Name

English

EBASTINE [JAN]

Common Name

English

EBASTINE [INN]

Common Name

English

EBASTINE [MI]

Common Name

English

EBASTINE [EP]

Common Name

English

Classification Tree Code System Code

WHO-ATC

R06AX22