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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

Description

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

CNS Non-penetrant
977
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.

Originator

Approval Year

Unknown
116683
Targets

Targets

Primary TargetPharmacologyConditionPotency
Histamine H1 receptor
300
Target ID: P35367
Gene ID: 3269
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
Antagonist
2577
Chronic idiopathic urticaria
Allergic rhinitis
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Histamine H1 receptor
Approved
7997
EBATROL
Primary
Histamine H1 receptor
Approved
7997
EBATROL
PubMed

PubMed

TitleDatePubMed
[Effect of H1 histamine receptor antagonists on T cell functions].
2003 Nov
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
Pharmacokinetics and safety of ebastine in patients with impaired hepatic function compared with healthy volunteers: a phase I open-label study.
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
Human CYP4F12 genetic polymorphism: identification and functional characterization of seven variant allozymes.
2004 Dec 15
Simultaneous determination of ebastine and its three metabolites in plasma using liquid chromatography-tandem mass spectrometry.
2004 Dec 25
Anti-inflammatory activity of H1-receptor antagonists: review of recent experimental research.
2004 Jan
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
Microbial oxidation of terfenadine and ebastine into fexofenadine and carebastine.
2004 Nov 1
Pharmacological management of allergic rhinitis in the elderly: safety issues with oral antihistamines.
2005
Management of persistent allergic rhinitis: evidence-based treatment with levocetirizine.
2005 Dec
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
Identification and functional characterization of novel CYP2J2 variants: G312R variant causes loss of enzyme catalytic activity.
2005 Feb
Collection of medical drug information in pharmacies: Drug Event Monitoring (DEM) in Japan.
2005 Jul
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.
2005 Mar
Safety of ebastine.
2005 Mar
Co-administration of ketoconazole with H1-antagonists ebastine and loratadine in healthy subjects: pharmacokinetic and pharmacodynamic effects.
2005 Mar
[Cardiac arrest following treatment with non-cardiologic QT-interval-increasing medications].
2005 May 2
Stimulating effects of H1-antagonists.
2006
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
Long QT syndrome in a patient with allergic rhinoconjunctivitis and auto-immune diabetes: focus on the choice of anti-H1 drugs.
2006 Dec
Inter-individual variation of cytochrome P4502J2 expression and catalytic activities in liver microsomes from Japanese and Caucasian populations.
2006 Dec
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
[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
Rupatadine: pharmacological profile and its use in the treatment of allergic disorders.
2006 Oct
Desloratadine for chronic idiopathic urticaria: a review of clinical efficacy.
2007
[Ebastine (kestine 20) in therapy of allergic rhinitis].
2007
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
Pharmacokinetics and safety of ebastine in healthy subjects and patients with renal impairment.
2007
Rupatadine: a review of its use in the management of allergic disorders.
2007
Selective, competitive and mechanism-based inhibitors of human cytochrome P450 2J2.
2007 Aug 15
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
Acquired cold urticaria symptoms can be safely prevented by ebastine.
2007 Dec
[New generation antihistamines as monotherapy or in combination. What is the relevance for daily clinical routine for allergic rhinoconjunctivitis].
2007 Jun
Palmoplantar pityriasis rosea: two case reports.
2007 Mar
[Peripheral anticholinergic syndrome].
2007 Mar-Apr
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
Human enteric microsomal CYP4F enzymes O-demethylate the antiparasitic prodrug pafuramidine.
2007 Nov
[Ebastine-induced hepatotoxicity].
2007 Oct
Ebastine improves nasal symptoms and airflow and affects response to decongestion test in patients with persistent allergic rhinitis: a pilot study.
2007 Sep-Oct
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

Patents

20010022978
1
JP2006117535A
1

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
  • 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
Related Record Type Details
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
HISTAMINE H1 RECEPTOR
TARGET -> INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
CYTOCHROME P450 2J2
METABOLIC ENZYME -> SUBSTRATE
ACTIVATOR
Related Record Type Details
Structure of CAREBASTINE
METABOLITE -> PARENT
Structure of HYDROXYEBASTINE
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
Structure of 1-(4-(1,1-DIMETHYLETHYL)PHENYL)-4-(CIS-4-(DIPHENYLMETHOXY)-1-OXIDOPIPERIDIN-1-YL)-BUTAN-1-ONE
IMPURITY -> PARENT
Structure of 1-(4-(1,1-DIMETHYLETHYL)PHENYL)-4-(4-HYDROXYPIPERIDIN-1-YL)BUTAN-1-ONE
IMPURITY -> PARENT
Related Record Type Details
Structure of EBASTINE
ACTIVE MOIETY
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