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 315 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 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340	Primary		Approved 8429	EBATROL Approved Use Unknown
Chronic idiopathic urticaria 11 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340	Primary		Approved 8429	EBATROL Approved Use Unknown

PubMed

Title	Date	PubMed
The non-cardiac systemic side-effects of antihistamines: ebastine.	1999 Jul	10444230
The effects of single and repeated administration of ebastine on cognition and psychomotor performance in comparison to triprolidine and placebo in healthy volunteers.	2001	11922401
cDNA cloning and expression of a novel cytochrome p450 (cyp4f12) from human small intestine.	2001 Feb 2	11162645
A novel cytochrome P450 enzyme responsible for the metabolism of ebastine in monkey small intestine.	2001 Jun	11353747
Simultaneous determination of the histamine H1-receptor antagonist ebastine and its two metabolites, carebastine and hydroxyebastine, in human plasma using high-performance liquid chromatography.	2001 Jun 5	11419742
Anaphylactoid reaction caused by moxifloxacin.	2002	12109537
Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests.	2002 Apr	11906367
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
Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes.	2002 Jan	11752129
Gateways to Clinical Trials. June 2002.	2002 Jun	12168506
Effects of second generation of histamine H1 antagonists, cetirizine and ebastine, on the antitussive and rewarding effects of dihydrocodeine in mice.	2003 Mar	12536265
[Antihistaminics. Side effects also after raising dosage at the placebo level].	2003 May 29	12866280
[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
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
Pharmacokinetics and safety of ebastine in patients with impaired hepatic function compared with healthy volunteers: a phase I open-label study.	2004	14748620
Expression of CYP4F12 in gastrointestinal and urogenital epithelia.	2004 Apr	15078342
Simultaneous determination of ebastine and its three metabolites in plasma using liquid chromatography-tandem mass spectrometry.	2004 Dec 25	15556518
Anti-inflammatory activity of H1-receptor antagonists: review of recent experimental research.	2004 Jan	14741075
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.	2004 Mar	15049392
Pharmacological management of allergic rhinitis in the elderly: safety issues with oral antihistamines.	2005	15839718
Safety of ebastine.	2005 Mar	15801255
Co-administration of ketoconazole with H1-antagonists ebastine and loratadine in healthy subjects: pharmacokinetic and pharmacodynamic effects.	2005 Mar	15752381
[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
Rupatadine: pharmacological profile and its use in the treatment of allergic disorders.	2006 Oct	17020424
Rupatadine: a review of its use in the management of allergic disorders.	2007	17335300
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

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 Dec 15 15:41:39 GMT 2023` Edited by `admin` on `Fri Dec 15 15:41:39 GMT 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