EBASTINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C32H39NO2
Molecular Weight	469.6576
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)C1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)OC(C3=CC=CC=C3)C4=CC=CC=C4

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	469.6576
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 313 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 2760

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340	Primary		Approved 8360	EBATROL Approved Use Unknown
Chronic idiopathic urticaria 11 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340	Primary		Approved 8360	EBATROL Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of the histamine wheal by ebastine compared with cetirizine, fexofenadine and loratadine at steady state.	2002	12776578
Chronic urticaria: a role for newer immunomodulatory drugs?	2003	12688835
Implementation of guidelines for seasonal allergic rhinitis: a randomized controlled trial.	2003 Aug	12859551
Rabbit aorta converts 15-HPETE to trihydroxyeicosatrienoic acids: potential role of cytochrome P450.	2003 Dec 1	14622984
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
[Effect of H1 histamine receptor antagonists on T cell functions].	2003 Nov	14685035
A study comparing the inhibitory effects of single and repeated oral doses of ebastine and fexofenadine against histamine-induced skin reactivity.	2003 Nov	14646388
Ebastine inhibits T cell migration, production of Th2-type cytokines and proinflammatory cytokines.	2003 Nov	14616867
Fixed drug eruption due to loratadine.	2003 Sep-Oct	14572420
Cetirizine: a review of its use in allergic disorders.	2004	14977391
Pharmacokinetics and safety of ebastine in patients with impaired hepatic function compared with healthy volunteers: a phase I open-label study.	2004	14748620
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
Human CYP4F12 genetic polymorphism: identification and functional characterization of seven variant allozymes.	2004 Dec 15	15548388
Anti-inflammatory activity of H1-receptor antagonists: review of recent experimental research.	2004 Jan	14741075
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
Microbial oxidation of terfenadine and ebastine into fexofenadine and carebastine.	2004 Nov 1	15454238
Management of persistent allergic rhinitis: evidence-based treatment with levocetirizine.	2005 Dec	18360569
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
Collection of medical drug information in pharmacies: Drug Event Monitoring (DEM) in Japan.	2005 Jul	15997212
[Cardiac arrest following treatment with non-cardiologic QT-interval-increasing medications].	2005 May 2	15929273
Stimulating effects of H1-antagonists.	2006	16842173
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
Long QT syndrome in a patient with allergic rhinoconjunctivitis and auto-immune diabetes: focus on the choice of anti-H1 drugs.	2006 Dec	17274518
Inter-individual variation of cytochrome P4502J2 expression and catalytic activities in liver microsomes from Japanese and Caucasian populations.	2006 Dec	17162467
CYP4F enzymes are the major enzymes in human liver microsomes that catalyze the O-demethylation of the antiparasitic prodrug DB289 [2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime].	2006 Dec	16997912
[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
Rupatadine: pharmacological profile and its use in the treatment of allergic disorders.	2006 Oct	17020424
Desloratadine for chronic idiopathic urticaria: a review of clinical efficacy.	2007	17902729
[Ebastine (kestine 20) in therapy of allergic rhinitis].	2007	17768822
A comparison of ebastine 10 mg fast-dissolving tablet with oral desloratadine and placebo in inhibiting the cutaneous reaction to histamine in healthy adults.	2007	17563125
Pharmacokinetics and safety of ebastine in healthy subjects and patients with renal impairment.	2007	17518511
Rupatadine: a review of its use in the management of allergic disorders.	2007	17335300
Selective, competitive and mechanism-based inhibitors of human cytochrome P450 2J2.	2007 Aug 15	17470359
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
Acquired cold urticaria symptoms can be safely prevented by ebastine.	2007 Dec	17900265
[New generation antihistamines as monotherapy or in combination. What is the relevance for daily clinical routine for allergic rhinoconjunctivitis].	2007 Jun	17566806
Palmoplantar pityriasis rosea: two case reports.	2007 Mar	17309476
[Peripheral anticholinergic syndrome].	2007 Mar-Apr	17542247
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 May	17697901
Human enteric microsomal CYP4F enzymes O-demethylate the antiparasitic prodrug pafuramidine.	2007 Nov	17709372
[Ebastine-induced hepatotoxicity].	2007 Oct	17949619
Ebastine improves nasal symptoms and airflow and affects response to decongestion test in patients with persistent allergic rhinitis: a pilot study.	2007 Sep-Oct	17883885
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 `Wed Jul 05 23:10:35 UTC 2023` Edited by `admin` on `Wed Jul 05 23:10:35 UTC 2023`
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

RP 64305

Code

English

LAS-W-090

Code

English

EBASTINE [EP IMPURITY]

Common Name

English

Ebastine [WHO-DD]

Common Name

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

Classification Tree Code System Code

WHO-ATC

R06AX22