ASTEMIZOLE

US Previously Marketed

First approved in 1988

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 Search

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

Description
Sources: https://www.drugs.com/mtm/astemizole.html

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 The drug was withdrawn from U.S. market in 1999 due to the potential to cause arrhythmias at high doses.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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21944853	Antagonist 2849		8.68 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seasonal allergic rhinitis 64 Sources: http://www.druglib.com/activeingredient/astemizole/	Primary		Withdrawn	HISMANAL Approved Use For the relief of symptoms associated with seasonal allergic rhinitis and chronic idiopathic urticaria. Launch Date 1984
Chronic idiopathic urticaria 11 Sources: http://www.druglib.com/activeingredient/astemizole/	Primary		Withdrawn	HISMANAL Approved Use For the relief of symptoms associated with seasonal allergic rhinitis and chronic idiopathic urticaria. Launch Date 1984

C_max

Value	Dose	Co-administered	Analyte	Population
1.9 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10423595	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10423595	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

Value	Dose	Co-administered	Analyte	Population
28.4 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10423595	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10423595	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10423595	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10423595	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

Dose	Population	Adverse events
6 mg/kg single, oral Overdose Dose: 6 mg/kg Route: oral Route: single Dose: 6 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	healthy, 1.5 years Health Status: healthy Age Group: 1.5 years Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	Other AEs: Ventricular tachycardia, Bundle branch block right... Other AEs: Ventricular tachycardia (serious) Bundle branch block right (serious) QT interval prolonged (serious) Sources: https://pubmed.ncbi.nlm.nih.gov/1578320
740 mg single, oral Overdose Dose: 740 mg Route: oral Route: single Dose: 740 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8189766	healthy, 22 years Health Status: healthy Age Group: 22 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8189766	Other AEs: Arrhythmia ventricular... Other AEs: Arrhythmia ventricular (serious) Sources: https://pubmed.ncbi.nlm.nih.gov/8189766
30 mg single, oral Overdose Dose: 30 mg Route: oral Route: single Dose: 30 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	healthy, 4 years Health Status: healthy Age Group: 4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	Other AEs: QT interval prolonged, Arrhythmia ventricular... Other AEs: QT interval prolonged (serious) Arrhythmia ventricular (serious) Heart block atrioventricular (serious) Sources: https://pubmed.ncbi.nlm.nih.gov/1578320

AEs

AE	Significance	Dose	Population
Bundle branch block right	serious	6 mg/kg single, oral Overdose Dose: 6 mg/kg Route: oral Route: single Dose: 6 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	healthy, 1.5 years Health Status: healthy Age Group: 1.5 years Sources: https://pubmed.ncbi.nlm.nih.gov/1578320
QT interval prolonged	serious	6 mg/kg single, oral Overdose Dose: 6 mg/kg Route: oral Route: single Dose: 6 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	healthy, 1.5 years Health Status: healthy Age Group: 1.5 years Sources: https://pubmed.ncbi.nlm.nih.gov/1578320
Ventricular tachycardia	serious	6 mg/kg single, oral Overdose Dose: 6 mg/kg Route: oral Route: single Dose: 6 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	healthy, 1.5 years Health Status: healthy Age Group: 1.5 years Sources: https://pubmed.ncbi.nlm.nih.gov/1578320
Arrhythmia ventricular	serious	740 mg single, oral Overdose Dose: 740 mg Route: oral Route: single Dose: 740 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8189766	healthy, 22 years Health Status: healthy Age Group: 22 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8189766
Arrhythmia ventricular	serious	30 mg single, oral Overdose Dose: 30 mg Route: oral Route: single Dose: 30 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	healthy, 4 years Health Status: healthy Age Group: 4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/1578320
Heart block atrioventricular	serious	30 mg single, oral Overdose Dose: 30 mg Route: oral Route: single Dose: 30 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	healthy, 4 years Health Status: healthy Age Group: 4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/1578320
QT interval prolonged	serious	30 mg single, oral Overdose Dose: 30 mg Route: oral Route: single Dose: 30 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1578320	healthy, 4 years Health Status: healthy Age Group: 4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/1578320

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 BCRP 910	CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C18 149 CYP2C19 1119 CYP2E1 729 CYP4A11 137 UGT 219 CYP2J2 71

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16406207/	yes [IC50 2.73 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17616561/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	yes
CYP2J2 71	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/26899760/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	yes
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259984/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2896	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2896
ChemicalBook	CB6741448	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6741448
eMolecules	534476	https://www.emolecules.com/cgi-bin/more?vid=534476
MolPort	MolPort-003-666-765	https://www.molport.com/shop/molecule-link/MolPort-003-666-765
ZINC	ZINC000000601274	http://zinc15.docking.org/substances/ZINC000000601274

PubMed

Title	Date	PubMed
A new model of allergic rhinitis in rats by topical sensitization and evaluation of H(1)-receptor antagonists.	2000 Jun	10822083
Redox state dependency of HERGS631C channel pharmacology: relation to C-type inactivation.	2000 May 26	10828461
Saquinavir soft gelatin capsule: a comparative safety review.	2001	11347724
A case series of drug-induced long QT syndrome and Torsade de Pointes.	2001 Dec	11989578
Triamcinolone: new and old indications.	2001 Jul	11583068
Antihistamines and the torsade de point in children with allergic rhinitis.	2001 Jul-Aug	12067082
Potential cardiac toxicity of H1-antihistamines.	2002	12113224
Cardiotoxicity of new antihistamines and cisapride.	2002 Feb 28	12052668
Next generation antihistamines: therapeutic rationale, accomplishments and advances.	2002 Jun	12036424
Development of telemetry system in the common marmoset--cardiovascular effects of astemizole and nicardipine.	2002 May	12058448
[Risk of drug interactions. Combinations of drugs associated with ventricular arrhythmias].	2002 May-Jun	12183887
[Effects of clinically available drugs on the repolarization process of the heart assessed by the in vivo canine models].	2003 Jun	12835533
Automated tight seal electrophysiology for assessing the potential hERG liability of pharmaceutical compounds.	2004 Oct	15671647
Mechanism of block of hEag1 K+ channels by imipramine and astemizole.	2004 Oct	15365094
Molecular cloning and kinetic characterization of an aldehyde dehydrogenase gene in Klebsiella pneumoniae.	2005 Apr	15909058
In vivo antimuscarinic actions of the third generation antihistaminergic agent, desloratadine.	2005 Aug 18	16109168
Identification of human P450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its kinetic parameters and inhibition constants.	2005 Feb	15684493
Evaluation of pharmacokinetic interaction between cetirizine and ritonavir, an HIV-1 protease inhibitor, in healthy male volunteers.	2005 Jun	15889300
Identifying modulators of hERG channel activity using the PatchXpress planar patch clamp.	2005 Mar	15799960

Patents

Sample Use Guides

In Vivo Use Guide

10 mg once daily, should be taken on an empty stomach

Route of Administration: Oral

In Vitro Use Guide

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

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Name

Type

Language

ASTEMIZOLE

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