Compound Detail
CHEMBL296419
ASTEMIZOLE 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL296419 |
| Name | ASTEMIZOLE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | GXDALQBWZGODGZ-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
76
Targets
204
Activities
4
Assay Types
16
PK Parameters
20
Publications
8
Known Names
1
Indications
1
Mechanisms
Molecular Properties
458.6
MW (Da)
5.35
ALogP
5
HBA
1
HBD
42.3
PSA (Ų)
0.39
QED
1
Ro5 Violations
8
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1988 |
| Availability | Withdrawn |
| Chirality | Achiral |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Histamine H1 receptor antagonist | ANTAGONIST | Histamine H1 receptor | ✓ | ✓ |
Indications
Hypersensitivity
ATC Classification
R06AX11
astemizole
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE
Drug Warnings
Withdrawn
General Warning
Increased risk of QT prolongation with concomitant administration of oral or parenteral formulations of azole antifungals, macrolide antibiotics except azithromycin, selective serotonin reuptake inhib...
Withdrawn
cardiotoxicity
Fatal arrhythmia; Drug Interaction
Withdrawn
cardiotoxicity
Cardiotoxic effects
Withdrawn
General Warning
Fatal arrhythmia; Drug Interaction
Withdrawn
cardiotoxicity
Rare but serious side-effects on heart, primary changes in heart rhythm
Withdrawn
cardiotoxicity
Associated with adverse drug reactions including irregular heart rhythms and severe allergic reactions if taken at higher than recommended doses or in conjunction with some other drugs including antih...
Withdrawn
cardiotoxicity
Serious adverse cardiovascular reactions
Withdrawn
General Warning
Several adverse reactions
Withdrawn
cardiotoxicity
Prolongation of the QT-interval and ventricular arrhythmias; Increased risk of QT prolongation with concomitant administration of oral or parenteral formulations of azole antifungals, macrolide antibi...
Withdrawn
immune system toxicity
Associated with adverse drug reactions including irregular heart rhythms and severe allergic reactions if taken at higher than recommended doses or in conjunction with some other drugs including antih...
Activity Summary
IC50 124 meas. best 9.05
Ki 62 meas. best 8.79
EC50 14 meas. best 8.72
Kd 4 meas. best 8.42
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240 | IC50 | 9.05 | 7.9479 | 0.9 | 24 |
| Histamine H1 receptor CHEMBL231 | Ki | 8.79 | 8.6633 | 1.6 | 3 |
| Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240 | EC50 | 8.72 | 8.72 | 1.9 | 1 |
| Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240 | Ki | 8.68 | 8.154 | 2.1 | 5 |
| Histamine H1 receptor CHEMBL3943 | Kd | 8.42 | 8.42 | 3.8 | 1 |
| ADMET CHEMBL612558 | Kd | 8.3 | 8.3 | 5.0 | 1 |
| No relevant target CHEMBL2362975 | Kd | 8.26 | 8.26 | 5.5 | 1 |
| 5-hydroxytryptamine receptor 2A CHEMBL224 | Ki | 8.25 | 8.25 | 5.6 | 1 |
| 5-hydroxytryptamine receptor 2B CHEMBL1833 | Ki | 8.13 | 8.13 | 7.5 | 1 |
| Alpha-1A adrenergic receptor CHEMBL319 | Ki | 8.0 | 8.0 | 9.9 | 1 |
| 5-hydroxytryptamine receptor 2B CHEMBL1833 | IC50 | 7.92 | 7.92 | 12.0 | 1 |
| Histamine H1 receptor CHEMBL231 | IC50 | 7.85 | 7.85 | 14.0 | 1 |
| 5-hydroxytryptamine receptor 2A CHEMBL224 | IC50 | 7.7 | 7.7 | 20.0 | 1 |
| Alpha-1A adrenergic receptor CHEMBL319 | IC50 | 7.62 | 7.62 | 24.0 | 1 |
| Unchecked CHEMBL612545 | Ki | 7.52 | 6.0944 | 30.0 | 9 |
| Unchecked CHEMBL612545 | IC50 | 7.48 | 5.4575 | 33.0 | 12 |
| RBL-2H3 CHEMBL614632 | IC50 | 7.27 | 7.0567 | 53.3 | 3 |
| Plasmodium falciparum CHEMBL364 | IC50 | 7.07 | 6.656 | 86.0 | 10 |
| 5-hydroxytryptamine receptor 2C CHEMBL225 | Ki | 7.03 | 7.03 | 94.0 | 1 |
| Alpha-1B adrenergic receptor CHEMBL315 | Ki | 7.02 | 7.02 | 95.0 | 1 |
| Sigma intracellular receptor 2 CHEMBL4105907 | Ki | 7.02 | 7.02 | 95.0 | 2 |
| Plasmodium berghei CHEMBL612653 | IC50 | 6.94 | 6.7033 | 114.0 | 3 |
| D(3) dopamine receptor CHEMBL234 | Ki | 6.83 | 6.83 | 148.0 | 1 |
| Alpha-1B adrenergic receptor CHEMBL315 | IC50 | 6.76 | 6.76 | 172.0 | 1 |
| 5-hydroxytryptamine receptor 2C CHEMBL225 | IC50 | 6.75 | 6.75 | 179.0 | 1 |
| Muscarinic acetylcholine receptor M3 CHEMBL245 | Ki | 6.75 | 6.75 | 178.0 | 1 |
| Muscarinic acetylcholine receptor M4 CHEMBL1821 | Ki | 6.59 | 6.59 | 259.0 | 1 |
| Muscarinic acetylcholine receptor M1 CHEMBL216 | Ki | 6.59 | 6.59 | 257.0 | 1 |
| Alpha-2C adrenergic receptor CHEMBL1916 | Ki | 6.54 | 6.54 | 285.0 | 1 |
| ATP-dependent translocase ABCB1 CHEMBL4302 | IC50 | 6.52 | 6.1 | 300.0 | 3 |
| Alpha-1D adrenergic receptor CHEMBL223 | Ki | 6.42 | 6.42 | 378.0 | 1 |
| D(3) dopamine receptor CHEMBL234 | IC50 | 6.36 | 6.36 | 436.0 | 1 |
| 5-hydroxytryptamine receptor 1A CHEMBL273 | Ki | 6.36 | 6.36 | 438.0 | 1 |
| Plasmodium falciparum CHEMBL364 | EC50 | 6.35 | 6.25 | 447.0 | 2 |
| Muscarinic acetylcholine receptor M5 CHEMBL2035 | Ki | 6.3 | 6.3 | 505.0 | 1 |
| Muscarinic acetylcholine receptor M2 CHEMBL211 | Ki | 6.3 | 6.3 | 501.0 | 1 |
| Mu-type opioid receptor CHEMBL233 | Ki | 6.22 | 6.22 | 606.0 | 1 |
| 5-hydroxytryptamine receptor 1B CHEMBL3459 | Ki | 6.2 | 6.2 | 630.0 | 1 |
| Sodium-dependent serotonin transporter CHEMBL228 | Ki | 6.16 | 6.16 | 700.0 | 1 |
| Muscarinic acetylcholine receptor M5 CHEMBL2035 | IC50 | 6.15 | 6.15 | 703.0 | 1 |
| 5-hydroxytryptamine receptor 1A CHEMBL273 | IC50 | 6.12 | 6.12 | 767.0 | 1 |
| Alpha-1D adrenergic receptor CHEMBL223 | IC50 | 6.11 | 6.11 | 769.0 | 1 |
| Sodium-dependent dopamine transporter CHEMBL238 | Ki | 6.1 | 6.1 | 793.0 | 1 |
| Muscarinic acetylcholine receptor M3 CHEMBL245 | IC50 | 6.08 | 6.08 | 840.0 | 1 |
| Sigma non-opioid intracellular receptor 1 CHEMBL287 | Ki | 6.03 | 5.9433 | 944.0 | 3 |
| Substance-K receptor CHEMBL2327 | Ki | 6.0 | 6.0 | 995.0 | 1 |
| Sodium-dependent dopamine transporter CHEMBL238 | IC50 | 6.0 | 6.0 | 998.0 | 1 |
| Muscarinic acetylcholine receptor M1 CHEMBL216 | IC50 | 5.97 | 5.97 | 1066.0 | 1 |
| Voltage-gated L-type calcium channel CHEMBL2095229 | IC50 | 5.96 | 5.96 | 1100.0 | 1 |
| SARS-CoV-2 CHEMBL4303835 | EC50 | 5.96 | 5.96 | 1100.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 11.01 | ng.hr.mL-1 | Homo sapiens |
| CL | 136.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 66.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 3.05 | uL/min | Homo sapiens |
| Fu | 0.011 | - | Rattus norvegicus |
| Fu | 0.004 | - | Rattus norvegicus |
| T1/2 | 26.0 | hr | Homo sapiens |
| T1/2 | 0.025 | hr | Homo sapiens |
| T1/2 | 0.06667 | hr | Homo sapiens |
| T1/2 | 1.0 | hr | Homo sapiens |
| T1/2 | 1.0 | hr | Homo sapiens |
| T1/2 | 1.0 | hr | Homo sapiens |
| T1/2 | 1.0 | hr | Homo sapiens |
| T1/2 | 1.0 | hr | Homo sapiens |
| T1/2 | 1.0 | hr | Rattus norvegicus |
| Vd | 48.0 | L.kg-1 | - |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine