Molecule Details
| InChIKey | IYIKLHRQXLHMJQ-UHFFFAOYSA-N |
|---|---|
| Compound Name | Amiodarone |
| Canonical SMILES | CCCCc1oc2ccccc2c1C(=O)c1cc(I)c(OCCN(CC)CC)c(I)c1 |
| Clinical Status | Data-mined Candidate |
| Targets (Human+Pathogen) | 18 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 6.61 |
| Source | ChEMBL;BindingDB |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB01118 |
|---|---|
| Drug Name | Amiodarone |
| CAS Number | 1951-25-3 |
| Groups | approved investigational |
| ATC Codes | C01BD01 |
| Description | Amiodarone is a benzofuran derivative, anti-arrhythmic drug used commonly in a variety of settings.[A36817] Most known for its approved indication in life-threatening ventricular arrhythmias, it is also used off-label in the outpatient and inpatient setting for atrial fibrillation. Because of its ab... |
Categories: Agents Causing Muscle Toxicity Agents causing hyperkalemia Antiarrhythmic agents Antiarrhythmics, Class III BSEP/ABCB11 Inhibitors BSEP/ABCB11 Substrates BSEP/ABCB11 Substrates with a Narrow Therapeutic Index Benzofurans Bradycardia-Causing Agents Calcium Channel Blockers Cardiac Therapy Cardiovascular Agents Cytochrome P-450 CYP1A1 Substrates Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (strong) Cytochrome P-450 CYP2A6 Inhibitors Cytochrome P-450 CYP2A6 Inhibitors (moderate) Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 Inhibitors (weak) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C19 inhibitors (strength unknown) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Inhibitors (strong) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates (strength unknown) Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Enzyme Inhibitors Heterocyclic Compounds, Fused-Ring Highest Risk QTc-Prolonging Agents Hypotensive Agents Membrane Transport Modulators Narrow Therapeutic Index Drugs OCT2 Inhibitors P-glycoprotein inducers P-glycoprotein inhibitors Photosensitizing Agents Potassium Channel Blockers QTc Prolonging Agents Sodium Channel Blockers Vasodilating Agents alpha-Galactosidase, antagonists & inhibitors
Cross-references: BindingDB: 18957 ChEBI: 2663 CHEMBL633 ChemSpider: 2072 Drugs Product Database (DPD): 1400 Guide to Pharmacology: 2566 IUPHAR: 2566 C06823 D02910 PDB: BBI PharmGKB: PA448383 PubChem:2157 PubChem:46507387 RxCUI: 703 Therapeutic Targets Database: DAP000496 Wikipedia: Amiodarone ZINC: ZINC000003830212
Target Activities (18)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| Q99720 | SIGMAR1 | Homo sapiens | Human | PF04622 | 8.2 | Ki | ChEMBL;BindingDB |
| Q15125 | EBP | Homo sapiens | Human | PF05241 | 7.6 | Ki | ChEMBL;BindingDB |
| Q12809 | KCNH2 | Homo sapiens | Human | PF00027 PF00520 PF13426 | 6.8 | IC50 | ChEMBL;BindingDB |
| P08913 | ADRA2A | Homo sapiens | Human | PF00001 | 6.7 | IC50 | ChEMBL |
| O60840 | CACNA1F | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.6 | IC50 | ChEMBL |
| Q01668 | CACNA1D | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.6 | IC50 | ChEMBL |
| Q13698 | CACNA1S | Homo sapiens | Human | PF08763 PF16905 PF00520 | 6.6 | IC50 | ChEMBL |
| Q13936 | CACNA1C | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.6 | IC50 | ChEMBL;BindingDB |
| P28335 | HTR2C | Homo sapiens | Human | PF00001 | 6.5 | IC50 | ChEMBL |
| P35462 | DRD3 | Homo sapiens | Human | PF00001 | 6.4 | Ki | ChEMBL |
| P08173 | CHRM4 | Homo sapiens | Human | PF00001 | 6.3 | Ki | ChEMBL |
| P10828 | THRB | Homo sapiens | Human | PF00104 PF00105 | 6.2 | IC50 | ChEMBL;BindingDB |
| P11229 | CHRM1 | Homo sapiens | Human | PF00001 | 6.2 | Ki | ChEMBL |
| P10827 | THRA | Homo sapiens | Human | PF00104 PF00105 | 6.2 | IC50 | ChEMBL;BindingDB |
| P20309 | CHRM3 | Homo sapiens | Human | PF00001 | 6.2 | Ki | ChEMBL |
| P41595 | HTR2B | Homo sapiens | Human | PF00001 | 6.1 | IC50 | ChEMBL |
| P06241 | FYN | Homo sapiens | Human | PF07714 PF00017 PF00018 | 6.1 | IC50 | ChEMBL |
| P32352 | ERG2 | Saccharomyces cerevisiae (strain ATCC 204508 / S288c) | Pathogen | PF04622 | 7.2 | Ki | ChEMBL;BindingDB |
DrugBank Target Actions (27)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P02768 | ALB | Albumin | binder | carriers |
| P05177 | CYP1A2 | Cytochrome P450 1A2 | inhibitor | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | inhibitor | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | inhibitor | enzymes |
| P11509 | CYP2A6 | Cytochrome P450 2A6 | inhibitor | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | inhibitor | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | inhibitor | enzymes |
| P51589 | CYP2J2 | Cytochrome P450 2J2 | inhibitor | enzymes |
| P04798 | CYP1A1 | Cytochrome P450 1A1 | substrate | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10632 | CYP2C8 | Cytochrome P450 2C8 | substrate | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | substrate | enzymes |
| P37231 | PPARG | Peroxisome proliferator-activated receptor gamma | agonist | targets |
| Q07869 | PPARA | Peroxisome proliferator-activated receptor alpha | agonist | targets |
| Q86YN6 | Q86YN6 | Peroxisome proliferator-activated receptor gamma coactivator 1-beta | agonist | targets |
| P10827 | THRA | Thyroid hormone receptor | antagonist | targets |
| P10827 | THRA | Thyroid hormone receptor | binder | targets |
| P08588 | ADRB1 | Beta adrenergic receptor | downregulator | targets |
| P08588 | ADRB1 | Beta adrenergic receptor | inhibitor | targets |
| Q12809 | KCNH2 | HERG human cardiac K+ channel | inhibitor | targets |
| Q13936 | CACNA1C | Voltage gated L-type calcium channel | inhibitor | targets |
| Q9P0X4 | CACNA1I | Voltage-dependent T-type calcium channel subunit alpha-1I | inhibitor | targets |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | inducer | transporters |
| O15244 | SLC22A2 | Solute carrier family 22 member 2 | inhibitor | transporters |
| O95342 | ABCB11 | Bile salt export pump | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | inhibitor | transporters |
| O95342 | ABCB11 | Bile salt export pump | substrate | transporters |