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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 of EBASTINE

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

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
The non-cardiac systemic side-effects of antihistamines: ebastine.
1999 Jul
[The effect of second generation histamine antagonists on the heart].
2001
Safety of antihistamines in children.
2001
Problems of heart rate correction in assessment of drug-induced QT interval prolongation.
2001 Apr
Effects of supratherapeutic doses of ebastine and terfenadine on the QT interval.
2001 Aug
A novel cytochrome P450 enzyme responsible for the metabolism of ebastine in monkey small intestine.
2001 Jun
Effect of age and gender on the pharmacokinetics of ebastine after single and repeated dosing in healthy subjects.
2001 Mar
Azelastine tablets in the treatment of chronic idiopathic urticaria. Phase iii, randomised, double-blind, placebo and active controlled multicentric clinical trial.
2001 Mar-Apr
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
Urticaria to cetirizine.
2002
Anaphylactoid reaction caused by moxifloxacin.
2002
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].
2002
In vivo evidence for a lack of central effect of ebastine, an antihistaminic agent, in rats: a microdialysis study.
2002 Dec
Comparative pharmacology of H1 antihistamines: clinical relevance.
2002 Dec 16
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
Differential cognitive effects of ebastine and (+)-chlorpheniramine in healthy subjects: correlation between cognitive impairment and plasma drug concentration.
2002 Mar
Involvement of CYP2J2 on the intestinal first-pass metabolism of antihistamine drug, astemizole.
2002 Nov
Efficacy of ebastine, cetirizine, and loratadine in histamine cutaneous challenges.
2002 Sep
Chronic urticaria: a role for newer immunomodulatory drugs?
2003
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
Efficacy of ebastine in the control of nasal congestion associated with allergic rhinitis.
2003 Mar
Effects of second generation of histamine H1 antagonists, cetirizine and ebastine, on the antitussive and rewarding effects of dihydrocodeine in mice.
2003 Mar
[In seasonal and perennial rhinitis. Superiority to standard H1 blockers].
2003 May 29
[Antihistaminics. Side effects also after raising dosage at the placebo level].
2003 May 29
Fixed drug eruption due to loratadine.
2003 Sep-Oct
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
Cetirizine: a review of its use in allergic disorders.
2004
Expression of CYP4F12 in gastrointestinal and urogenital epithelia.
2004 Apr
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
A review of the second-generation antihistamine ebastine for the treatment of allergic disorders.
2004 Aug
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.
2004 Jul
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.
2004 Mar
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
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
[Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis].
2006 May
Acceptance survey of a fast dissolving tablet pharmaceutical formulation in allergic patients. Satisfaction and expectancies.
2006 May-Jun
Characterization of ebastine, hydroxyebastine, and carebastine metabolism by human liver microsomes and expressed cytochrome P450 enzymes: major roles for CYP2J2 and CYP3A.
2006 Nov
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
Rupatadine in allergic rhinitis and chronic urticaria.
2008 Apr
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 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
  • 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
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
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
WHO-VATC QR06AX22
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL305660
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
MERCK INDEX
M4801
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY Merck Index
CAS
90729-43-4
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
PUBCHEM
3191
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
DRUG CENTRAL
977
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
LACTMED
Ebastine
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
DRUG BANK
DB11742
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
RXCUI
23796
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY RxNorm
FDA UNII
TQD7Q784P1
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
INN
5633
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
EPA CompTox
90729-43-4
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
WIKIPEDIA
EBASTINE
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
MESH
C058249
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
NCI_THESAURUS
C77437
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
EVMPD
SUB06435MIG
Created by admin on Fri Jun 25 21:10:11 UTC 2021 , Edited by admin on Fri Jun 25 21:10:11 UTC 2021
PRIMARY
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