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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 of EBASTINE

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

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

Curator's Comment: Ebastine BBB transport was studied on rats, mice and bovine brain. Ebastine has shown limmited transport, while its active metabolite, carebastine, was effectively transported by P-gp.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35367
Gene ID: 3269.0
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EBATROL

Approved Use

Unknown
Primary
EBATROL

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Mechanism responsible for epileptogenic activity by first-generation H1-antagonists in rats.
2000 Dec 22
Treatment of urticaria. An evidence-based evaluation of antihistamines.
2001
Transport characteristics of ebastine and its metabolites across human intestinal epithelial Caco-2 cell monolayers.
2001 Aug
Effects of supratherapeutic doses of ebastine and terfenadine on the QT interval.
2001 Aug
cDNA cloning and expression of a novel cytochrome p450 (cyp4f12) from human small intestine.
2001 Feb 2
[Co-administration of histamine H1 antagonist and oral anticoagulants].
2001 Jun-Jul
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
[Clinical efficacy of Ebastine under placebo-controlled outdoors clinical study on cedar pollinosis].
2002 Apr
Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests.
2002 Apr
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
Cardiotoxicity of new antihistamines and cisapride.
2002 Feb 28
Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes.
2002 Jan
Gateways to Clinical Trials. June 2002.
2002 Jun
Comparative antiallergic effects of second-generation H1-antihistamines ebastine, cetirizine and loratadine in preclinical models.
2003
Effects of second generation of histamine H1 antagonists, cetirizine and ebastine, on the antitussive and rewarding effects of dihydrocodeine in mice.
2003 Mar
Fixed drug eruption due to loratadine.
2003 Sep-Oct
A review of the second-generation antihistamine ebastine for the treatment of allergic disorders.
2004 Aug
Simultaneous determination of ebastine and its three metabolites in plasma using liquid chromatography-tandem mass spectrometry.
2004 Dec 25
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.
2004 Jul
Management of persistent allergic rhinitis: evidence-based treatment with levocetirizine.
2005 Dec
Collection of medical drug information in pharmacies: Drug Event Monitoring (DEM) in Japan.
2005 Jul
[Cardiac arrest following treatment with non-cardiologic QT-interval-increasing medications].
2005 May 2
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
Characterization of ebastine, hydroxyebastine, and carebastine metabolism by human liver microsomes and expressed cytochrome P450 enzymes: major roles for CYP2J2 and CYP3A.
2006 Nov
[Ebastine-induced hepatotoxicity].
2007 Oct
Granular parakeratosis presenting with facial keratotic papules.
2008 Jan-Feb
Probing ligand binding modes of human cytochrome P450 2J2 by homology modeling, molecular dynamics simulation, and flexible molecular docking.
2008 May 1
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS).
2008 Sep
Patents

Sample Use Guides

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 16 17:52:51 UTC 2022
Edited
by admin
on Fri Dec 16 17:52:51 UTC 2022
Record UNII
TQD7Q784P1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EBASTINE
EP   INN   JAN   MART.   MI   USAN   USP-RS   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
WHO-VATC QR06AX22
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
NCI_THESAURUS C29578
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
Code System Code Type Description
ChEMBL
CHEMBL305660
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
MERCK INDEX
M4801
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY Merck Index
CAS
90729-43-4
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
PUBCHEM
3191
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
DRUG CENTRAL
977
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
LACTMED
Ebastine
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
DRUG BANK
DB11742
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
RXCUI
23796
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY RxNorm
FDA UNII
TQD7Q784P1
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
INN
5633
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
EPA CompTox
DTXSID6046472
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
WIKIPEDIA
EBASTINE
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
USAN
Y-98
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
MESH
C058249
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
NCI_THESAURUS
C77437
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
EVMPD
SUB06435MIG
Created by admin on Fri Dec 16 17:52:51 UTC 2022 , Edited by admin on Fri Dec 16 17:52:51 UTC 2022
PRIMARY
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