ASTEMIZOLE

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

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

Description

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 The drug was withdrawn from U.S. market in 1999 due to the potential to cause arrhythmias at high doses.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	Antagonist 2,849		8.68 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seasonal allergic rhinitis 64	Primary		Withdrawn	HISMANAL
Chronic idiopathic urticaria 11	Primary		Withdrawn	HISMANAL

C_max

Value	Dose	Co-administered	Analyte	Population
1.9 mg/L	30 mg single, oral		ASTEMIZOLE blood	Homo sapiens
2.1 mg/L	30 mg single, oral		DESMETHYLASTEMIZOLE blood	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
28.4 mg × h/L	30 mg single, oral		ASTEMIZOLE blood	Homo sapiens
260 mg × h/L	30 mg single, oral		DESMETHYLASTEMIZOLE blood	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
25 h	30 mg single, oral		ASTEMIZOLE blood	Homo sapiens
223 h	30 mg single, oral		DESMETHYLASTEMIZOLE blood	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
6 mg/kg single, oral Overdose	healthy, 1.5 years	Other AEs: Ventricular tachycardia, Bundle branch block right...
740 mg single, oral Overdose	healthy, 22 years	Other AEs: Arrhythmia ventricular...
30 mg single, oral Overdose	healthy, 4 years	Other AEs: QT interval prolonged, Arrhythmia ventricular...

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AEs

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AE	Significance	Dose	Population
Bundle branch block right	serious	6 mg/kg single, oral Overdose	healthy, 1.5 years
QT interval prolonged	serious	6 mg/kg single, oral Overdose	healthy, 1.5 years
Ventricular tachycardia	serious	6 mg/kg single, oral Overdose	healthy, 1.5 years
Arrhythmia ventricular	serious	740 mg single, oral Overdose	healthy, 22 years
Arrhythmia ventricular	serious	30 mg single, oral Overdose	healthy, 4 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946	substrate 1,193	substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,741 BCRP 910	CYP1A1 389 CYP1A2 1,197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C18 149 CYP2C19 1,119 CYP2E1 729 CYP4A11 137 UGT 219 CYP2J2 71

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1,932	inhibitor 4,027	yes [IC50 2.73 uM]
BCRP 985	inhibitor 4,027	yes

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Drug as victim

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Target	Modality	Activity
CYP1A1 389	substrate 4,014	no
CYP1A2 1,197	substrate 4,014	no
CYP2A6 626	substrate 4,014	no
CYP2B6 776	substrate 4,014	no
CYP2C18 149	substrate 4,014	no

Showing 1 to 5 of 14 entries

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
A new model of allergic rhinitis in rats by topical sensitization and evaluation of H(1)-receptor antagonists.	2000 Jun	10822083
[Effect of olopatadine hydrochloride, a novel antiallergic agent, on the QT interval in dogs].	2001 Jun	11436518
Determination of astemizole in pharmaceutical preparations using spectrophotometric methods.	2001 Jun	11377031
Antihistamines in late-phase clinical development for allergic disease.	2002 Feb	11829715
Assessment of the relationship between hyperalgesia and peripheral inflammation in magnesium-deficient rats.	2002 Jan 18	11860153

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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.

Show entries

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

Showing 1 to 5 of 15 entries

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Classification Tree

Code System

Code

Subpart B--Compounded Drug Products

CFR

21 CFR 216.24

Other antihistamines for systemic use

WHO-ATC

R06AX11

Other antihistamines for systemic use

WHO-VATC

QR06AX11

Immunotherapeutic Agent

NCI_THESAURUS

C29578

Showing 1 to 4 of 4 entries

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Code System

Code

Type

Description

SMS_ID

100000086629

PRIMARY

EPA CompTox

DTXSID9020110

PRIMARY

CAS

68844-77-9

PRIMARY

DRUG CENTRAL

249

PRIMARY

WIKIPEDIA

ASTEMIZOLE

PRIMARY

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ACTIVE MOIETY


					7HU6337315

ASTEMIZOLE

METABOLITE ACTIVE (PARENT)


					L460QHM1YN

DESMETHYLASTEMIZOLE

METABOLITE ACTIVE (PARENT)


					W5DCO14M05

TECASTEMIZOLE

SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="https://www.drugs.com/mtm/astemizole.html">https://www.drugs.com/mtm/astemizole.html</a></span></span></div></div>

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description

C_max

T_1/2

Drug as perpetrator