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)
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 |
DescriptionSources: https://www.drugs.com/mtm/astemizole.html
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 The drug was withdrawn from U.S. market in 1999 due to the potential to cause arrhythmias at high doses.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
Sources: https://ichapps.com/Drug/view/astemizole
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6124876
Curator's Comment: # Janssen Pharmaceuticals
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21944853 |
8.68 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | HISMANAL Approved UseFor the relief of symptoms associated with seasonal allergic rhinitis and chronic idiopathic urticaria. Launch Date1984 |
|||
Primary | HISMANAL Approved UseFor the relief of symptoms associated with seasonal allergic rhinitis and chronic idiopathic urticaria. Launch Date1984 |
Cmax
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 |
T1/2
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 |
healthy, 1.5 years |
Other AEs: Ventricular tachycardia, Bundle branch block right... Other AEs: Ventricular tachycardia (serious) Sources: Bundle branch block right (serious) QT interval prolonged (serious) |
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... Other AEs: QT interval prolonged (serious) Sources: Arrhythmia ventricular (serious) Heart block atrioventricular (serious) |
AEs
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 |
Heart block atrioventricular | serious | 30 mg single, oral Overdose |
healthy, 4 years |
QT interval prolonged | serious | 30 mg single, oral Overdose |
healthy, 4 years |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 2.73 uM] | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://ichapps.com/Drug/view/astemizole
10 mg once daily, should be taken on an empty stomach
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21944853
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
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on
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Record UNII |
7HU6337315
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 216.24
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WHO-ATC |
R06AX11
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WHO-VATC |
QR06AX11
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NCI_THESAURUS |
C29578
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100000086629
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ASTEMIZOLE
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272-441-9
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CHEMBL296419
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m2116
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C28834
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329963
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DB00637
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7HU6337315
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2896
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D016589
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2603
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
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OFF-TARGET->INHIBITOR |
BINDING
IC50
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TARGET -> INHIBITOR |
control substance
BINDING
IC50
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TARGET -> INHIBITOR |
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BIOSIMILAR -> PARENT |
BINDING
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
MAJOR
PLASMA
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METABOLITE ACTIVE -> PARENT |
MINOR
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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