U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
53.4 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CAREBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
97.7 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CAREBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3.71 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.98 ng/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.31 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.49 ng/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.91 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.58 ng/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.15 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age:
sex: MALE
food status: UNKNOWN
5.97 ng/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1417 ng × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CAREBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2630 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CAREBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
16.8 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
30.3 ng × h/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
14.9 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
28.8 ng × h/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.5 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.5 ng × h/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.5 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age:
sex: MALE
food status: UNKNOWN
25.9 ng × h/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18.1 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CAREBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
17.6 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CAREBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.3 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
24.8 h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.8 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
24.3 h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.4 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
23.6 h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.2 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age:
sex: MALE
food status: UNKNOWN
37.3 h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
EBASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
EBASTINE serum
Homo sapiens
2.3%
CAREBASTINE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
40 mg 1 times / day single, oral
Highest studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: single
Dose: 40 mg, 1 times / day
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
Other AEs: Headache, Drowsiness...
Other AEs:
Headache (7.9%)
Drowsiness (3%)
dry mouth (2.1%)
Sources:
60 mg single, oral
Overdose
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
AEs

AEs

AESignificanceDosePopulation
dry mouth 2.1%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
Drowsiness 3%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
Headache 7.9%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 10.964 uM]
inconclusive [IC50 15.4871 uM]
no [EC50 3.0901 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no
no
no
yes [IC50 13.8029 uM]
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
major
no
no
no
no
no
no
no
no
yes [Km 0.75 uM]
yes [Km 1.3 uM]
yes [Km 21.9 uM]
yes [Km 3 uM]
yes [Km 3.85 uM]
yes [Km 5.56 uM]
yes [Km 7.63 uM]
yes [Km 7.67 uM]
yes
Tox targets
PubMed

PubMed

TitleDatePubMed
Mechanism responsible for epileptogenic activity by first-generation H1-antagonists in rats.
2000 Dec 22
Safety of antihistamines in children.
2001
Problems of heart rate correction in assessment of drug-induced QT interval prolongation.
2001 Apr
Transport characteristics of ebastine and its metabolites across human intestinal epithelial Caco-2 cell monolayers.
2001 Aug
Blockade of eosinophil migration and airway hyperresponsiveness by cPLA2-inhibition.
2001 Feb
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
Urticaria to cetirizine.
2002
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].
2002
Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes.
2002 Jan
[Effect of H1 histamine receptor antagonists on T cell functions].
2003 Nov
A study comparing the inhibitory effects of single and repeated oral doses of ebastine and fexofenadine against histamine-induced skin reactivity.
2003 Nov
Fixed drug eruption due to loratadine.
2003 Sep-Oct
Pharmacokinetics and safety of ebastine in patients with impaired hepatic function compared with healthy volunteers: a phase I open-label study.
2004
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
Anti-inflammatory activity of H1-receptor antagonists: review of recent experimental research.
2004 Jan
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
Identification and functional characterization of novel CYP2J2 variants: G312R variant causes loss of enzyme catalytic activity.
2005 Feb
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.
2005 Mar
Safety of ebastine.
2005 Mar
[Cardiac arrest following treatment with non-cardiologic QT-interval-increasing medications].
2005 May 2
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
[Ebastine-induced hepatotoxicity].
2007 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

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 Mon Mar 31 18:05:44 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:44 GMT 2025
Record UNII
TQD7Q784P1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAS-W-090
Preferred Name English
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
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 Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
WHO-VATC QR06AX22
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL305660
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
MERCK INDEX
m4801
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY Merck Index
CAS
90729-43-4
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
PUBCHEM
3191
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
DRUG CENTRAL
977
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
LACTMED
Ebastine
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
DRUG BANK
DB11742
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
RXCUI
23796
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY RxNorm
SMS_ID
100000092562
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
FDA UNII
TQD7Q784P1
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
INN
5633
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID6046472
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
WIKIPEDIA
EBASTINE
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
USAN
Y-98
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
MESH
C058249
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
NCI_THESAURUS
C77437
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
EVMPD
SUB06435MIG
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
ACTIVATOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY