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Details

Stereochemistry ACHIRAL
Molecular Formula C28H31FN4O
Molecular Weight 458.5703
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASTEMIZOLE

SMILES

COC1=CC=C(CCN2CCC(CC2)NC3=NC4=C(C=CC=C4)N3CC5=CC=C(F)C=C5)C=C1

InChI

InChIKey=GXDALQBWZGODGZ-UHFFFAOYSA-N
InChI=1S/C28H31FN4O/c1-34-25-12-8-21(9-13-25)14-17-32-18-15-24(16-19-32)30-28-31-26-4-2-3-5-27(26)33(28)20-22-6-10-23(29)11-7-22/h2-13,24H,14-20H2,1H3,(H,30,31)

HIDE SMILES / InChI

Molecular Formula C28H31FN4O
Molecular Weight 458.5703
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Astemizole is antihistamine drug, discovered by Janssen Pharmaceutical and used to prevent sneezing, runny nose, itching and watering of the eyes, and other allergic symptoms. The drug was withdrawn from U.S. market in 1999 due to the potential to cause arrhythmias at high doses.

CNS Activity

Curator's Comment: Astemizole is a second generation H1-receptor antagonist. It does not cross the BBB significantly due to this reason do not cause CNS depression or drowsiness at normal doses.

Originator

Curator's Comment: # Janssen Pharmaceuticals

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.68 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HISMANAL

Approved Use

For the relief of symptoms associated with seasonal allergic rhinitis and chronic idiopathic urticaria.

Launch Date

1984
Primary
HISMANAL

Approved Use

For the relief of symptoms associated with seasonal allergic rhinitis and chronic idiopathic urticaria.

Launch Date

1984
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.9 mg/L
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ASTEMIZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.1 mg/L
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESMETHYLASTEMIZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
28.4 mg × h/L
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ASTEMIZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
260 mg × h/L
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESMETHYLASTEMIZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
25 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ASTEMIZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
223 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESMETHYLASTEMIZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
6 mg/kg single, oral
Overdose
Dose: 6 mg/kg
Route: oral
Route: single
Dose: 6 mg/kg
Sources:
healthy, 1.5 years
Health Status: healthy
Age Group: 1.5 years
Sources:
Other AEs: Ventricular tachycardia, Bundle branch block right...
Other AEs:
Ventricular tachycardia (serious)
Bundle branch block right (serious)
QT interval prolonged (serious)
Sources:
740 mg single, oral
Overdose
Dose: 740 mg
Route: oral
Route: single
Dose: 740 mg
Sources:
healthy, 22 years
Health Status: healthy
Age Group: 22 years
Sex: M
Sources:
Other AEs: Arrhythmia ventricular...
Other AEs:
Arrhythmia ventricular (serious)
Sources:
30 mg single, oral
Overdose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
healthy, 4 years
Health Status: healthy
Age Group: 4 years
Sex: M
Sources:
Other AEs: QT interval prolonged, Arrhythmia ventricular...
Other AEs:
QT interval prolonged (serious)
Arrhythmia ventricular (serious)
Heart block atrioventricular (serious)
Sources:
AEs

AEs

AESignificanceDosePopulation
Bundle branch block right serious
6 mg/kg single, oral
Overdose
Dose: 6 mg/kg
Route: oral
Route: single
Dose: 6 mg/kg
Sources:
healthy, 1.5 years
Health Status: healthy
Age Group: 1.5 years
Sources:
QT interval prolonged serious
6 mg/kg single, oral
Overdose
Dose: 6 mg/kg
Route: oral
Route: single
Dose: 6 mg/kg
Sources:
healthy, 1.5 years
Health Status: healthy
Age Group: 1.5 years
Sources:
Ventricular tachycardia serious
6 mg/kg single, oral
Overdose
Dose: 6 mg/kg
Route: oral
Route: single
Dose: 6 mg/kg
Sources:
healthy, 1.5 years
Health Status: healthy
Age Group: 1.5 years
Sources:
Arrhythmia ventricular serious
740 mg single, oral
Overdose
Dose: 740 mg
Route: oral
Route: single
Dose: 740 mg
Sources:
healthy, 22 years
Health Status: healthy
Age Group: 22 years
Sex: M
Sources:
Arrhythmia ventricular serious
30 mg single, oral
Overdose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
healthy, 4 years
Health Status: healthy
Age Group: 4 years
Sex: M
Sources:
Heart block atrioventricular serious
30 mg single, oral
Overdose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
healthy, 4 years
Health Status: healthy
Age Group: 4 years
Sex: M
Sources:
QT interval prolonged serious
30 mg single, oral
Overdose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
healthy, 4 years
Health Status: healthy
Age Group: 4 years
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 2.73 uM]
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
A new model of allergic rhinitis in rats by topical sensitization and evaluation of H(1)-receptor antagonists.
2000 Jun
Redox state dependency of HERGS631C channel pharmacology: relation to C-type inactivation.
2000 May 26
Saquinavir soft gelatin capsule: a comparative safety review.
2001
A case series of drug-induced long QT syndrome and Torsade de Pointes.
2001 Dec
Triamcinolone: new and old indications.
2001 Jul
Antihistamines and the torsade de point in children with allergic rhinitis.
2001 Jul-Aug
Potential cardiac toxicity of H1-antihistamines.
2002
Cardiotoxicity of new antihistamines and cisapride.
2002 Feb 28
Next generation antihistamines: therapeutic rationale, accomplishments and advances.
2002 Jun
Development of telemetry system in the common marmoset--cardiovascular effects of astemizole and nicardipine.
2002 May
[Risk of drug interactions. Combinations of drugs associated with ventricular arrhythmias].
2002 May-Jun
[Effects of clinically available drugs on the repolarization process of the heart assessed by the in vivo canine models].
2003 Jun
Automated tight seal electrophysiology for assessing the potential hERG liability of pharmaceutical compounds.
2004 Oct
Mechanism of block of hEag1 K+ channels by imipramine and astemizole.
2004 Oct
Molecular cloning and kinetic characterization of an aldehyde dehydrogenase gene in Klebsiella pneumoniae.
2005 Apr
In vivo antimuscarinic actions of the third generation antihistaminergic agent, desloratadine.
2005 Aug 18
Identification of human P450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its kinetic parameters and inhibition constants.
2005 Feb
Evaluation of pharmacokinetic interaction between cetirizine and ritonavir, an HIV-1 protease inhibitor, in healthy male volunteers.
2005 Jun
Identifying modulators of hERG channel activity using the PatchXpress planar patch clamp.
2005 Mar
Patents

Patents

Sample Use Guides

In Vivo Use Guide
10 mg once daily, should be taken on an empty stomach
Route of Administration: Oral
Affinity at histamine H1 receptor was measured in Sf9 cells transfected with H1 and coexpressing Regulator Of G-Protein Signaling 4 (RGS4). [3H]Mepyramine was used a radiolabel in a competition binding assay. pKi of astemizole was 8.68.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:13:23 GMT 2025
Edited
by admin
on Mon Mar 31 18:13:23 GMT 2025
Record UNII
7HU6337315
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASTEMIZOLE
HSDB   INN   JAN   MART.   MI   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NSC-329963
Preferred Name English
Astemizole [WHO-DD]
Common Name English
ASTEMIZOLE [USAN]
Common Name English
ASTEMIZOLE [MI]
Common Name English
astemizole [INN]
Common Name English
ASTEMIZOLE [USP IMPURITY]
Common Name English
1-(P-FLUOROBENZYL)-2-((1-(P-METHOXYPHENETHYL)-4-PIPERIDYL)AMINO)BENZIMIDAZOLE
Common Name English
ASTEMIZOLE [JAN]
Common Name English
ASTEMIZOLE [VANDF]
Common Name English
R 43,512
Code English
ASTEMIZOLE [HSDB]
Common Name English
1H-BENZIMIDAZOL-2-AMINE, 1-((4-FLUOROPHENYL)METHYL)-N-(1-(2-(4-METHOXYPHENYL)ETHYL)-4-PIPERIDINYL)-
Systematic Name English
ASTEMIZOLE [MART.]
Common Name English
NSC-759570
Code English
Classification Tree Code System Code
CFR 21 CFR 216.24
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
WHO-ATC R06AX11
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
WHO-VATC QR06AX11
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
Code System Code Type Description
SMS_ID
100000086629
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID9020110
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
CAS
68844-77-9
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
DRUG CENTRAL
249
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
WIKIPEDIA
ASTEMIZOLE
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
ECHA (EC/EINECS)
272-441-9
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
ChEMBL
CHEMBL296419
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
HSDB
6799
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
INN
4755
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
NSC
759570
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
MERCK INDEX
m2116
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C28834
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
NSC
329963
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
EVMPD
SUB05586MIG
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
PUBCHEM
2247
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
RXCUI
42328
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB00637
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
FDA UNII
7HU6337315
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
CHEBI
2896
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
MESH
D016589
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
IUPHAR
2603
Created by admin on Mon Mar 31 18:13:23 GMT 2025 , Edited by admin on Mon Mar 31 18:13:23 GMT 2025
PRIMARY
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TARGET -> INHIBITOR
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Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC