Molecule Details
| InChIKey | SGTNSNPWRIOYBX-UHFFFAOYSA-N |
|---|---|
| Compound Name | Verapamil |
| Canonical SMILES | COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC |
| Clinical Status | Data-mined Candidate |
| Targets (Human+Pathogen) | 19 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 6.64 |
| Source | ChEMBL;BindingDB |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00661 |
|---|---|
| Drug Name | Verapamil |
| CAS Number | 52-53-9 |
| Groups | approved investigational |
| ATC Codes | C09BB10 C08DA51 C08DA01 |
| Description | Verapamil is a phenylalkylamine calcium channel blocker used in the treatment of high blood pressure, heart arrhythmias, and angina,[L8791] and was the first calcium channel antagonist to be introduced into therapy in the early 1960s.[A188514] It is a member of the non-dihydropyridine class of calci... |
Categories: ACE Inhibitors and Calcium Channel Blockers Adrenergic Antagonists Adrenergic alpha-1 Receptor Antagonists Adrenergic alpha-Antagonists Amines Antiarrhythmic agents Antihypertensive Agents Antihypertensive Agents Indicated for Hypertension Bradycardia-Causing Agents Calcium Channel Blockers Calcium Channel Blockers (Nondihydropyridine) Cardiovascular Agents Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2B6 Substrates Cytochrome P-450 CYP2C18 Substrates Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (weak) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2E1 Substrates Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (moderate) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (moderate) Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs that are Mainly Renally Excreted Hypotensive Agents MATE 1 Inhibitors MATE 2 Inhibitors MATE inhibitors Membrane Transport Modulators Miscellaneous Calcium-channel Blocking Agents Negative Inotrope OATP1B1/SLCO1B1 Inhibitors OCT1 inhibitors OCT1 substrates P-glycoprotein inhibitors P-glycoprotein substrates Phenylalkylamine Derivatives Selective Calcium Channel Blockers With Direct Cardiac Effects Vasodilating Agents Verapamil and analogues
Cross-references: BindingDB: 81939 ChEBI: 77733 CHEMBL6966 ChemSpider: 2425 Drugs Product Database (DPD): 10110 Guide to Pharmacology: 2406 IUPHAR: 2406 C07188 D02356 PharmGKB: PA451868 PubChem:2520 PubChem:46508158 RxCUI: 11170 Therapeutic Targets Database: DAP000040 Wikipedia: Verapamil
Target Activities (19)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P08684 | CYP3A4 | Homo sapiens | Human | PF00067 | 8.0 | IC50 | ChEMBL;BindingDB |
| P08183 | ABCB1 | Homo sapiens | Human | PF00664 PF00005 | 7.4 | IC50 | ChEMBL;BindingDB |
| P33527 | ABCC1 | Homo sapiens | Human | PF00664 PF00005 PF24357 | 7.1 | IC50 | ChEMBL |
| P35462 | DRD3 | Homo sapiens | Human | PF00001 | 7.0 | IC50 | ChEMBL |
| P41595 | HTR2B | Homo sapiens | Human | PF00001 | 6.9 | IC50 | ChEMBL |
| P31645 | SLC6A4 | Homo sapiens | Human | PF03491 PF00209 | 6.8 | IC50 | ChEMBL |
| Q13936 | CACNA1C | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.8 | IC50 | ChEMBL;BindingDB |
| O60840 | CACNA1F | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.7 | IC50 | ChEMBL |
| Q01668 | CACNA1D | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.7 | IC50 | ChEMBL |
| Q12809 | KCNH2 | Homo sapiens | Human | PF00027 PF00520 PF13426 | 6.7 | IC50 | ChEMBL;BindingDB |
| Q13698 | CACNA1S | Homo sapiens | Human | PF08763 PF16905 PF00520 | 6.7 | IC50 | ChEMBL |
| P28335 | HTR2C | Homo sapiens | Human | PF00001 | 6.7 | IC50 | ChEMBL |
| P28223 | HTR2A | Homo sapiens | Human | PF00001 | 6.6 | IC50 | ChEMBL |
| P08913 | ADRA2A | Homo sapiens | Human | PF00001 | 6.2 | IC50 | ChEMBL |
| P18089 | ADRA2B | Homo sapiens | Human | PF00001 | 6.0 | Kd | ChEMBL |
| P18825 | ADRA2C | Homo sapiens | Human | PF00001 | 6.0 | Kd | ChEMBL |
| P25100 | ADRA1D | Homo sapiens | Human | PF00001 | 6.0 | Kd | ChEMBL |
| P35348 | ADRA1A | Homo sapiens | Human | PF00001 | 6.0 | Kd | ChEMBL |
| P35368 | ADRA1B | Homo sapiens | Human | PF00001 | 6.0 | Kd | ChEMBL |
DrugBank Target Actions (44)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P02763 | P02763 | Alpha-1-acid glycoprotein 1 | substrate | carriers |
| P02768 | ALB | Albumin | substrate | carriers |
| P20813 | CYP2B6 | Cytochrome P450 2B6 | activator | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | inhibitor | enzymes |
| P10632 | CYP2C8 | Cytochrome P450 2C8 | inhibitor | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | inhibitor | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | inhibitor | enzymes |
| P20815 | CYP3A5 | Cytochrome P450 3A5 | inhibitor | enzymes |
| P05177 | CYP1A2 | Cytochrome P450 1A2 | substrate | enzymes |
| P05181 | CYP2E1 | Cytochrome P450 2E1 | substrate | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10632 | CYP2C8 | Cytochrome P450 2C8 | substrate | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | substrate | enzymes |
| P20813 | CYP2B6 | Cytochrome P450 2B6 | substrate | enzymes |
| P20815 | CYP3A5 | Cytochrome P450 3A5 | substrate | enzymes |
| P33260 | CYP2C18 | Cytochrome P450 2C18 | substrate | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | substrate | enzymes |
| P25100 | ADRA1D | Alpha-1D adrenergic receptor | antagonist | targets |
| P35348 | ADRA1A | Alpha-1A adrenergic receptor | antagonist | targets |
| P35368 | ADRA1B | Alpha-1B adrenergic receptor | antagonist | targets |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | blocker | targets |
| O00555 | CACNA1A | Voltage-dependent P/Q-type calcium channel subunit alpha-1A | inhibitor | targets |
| O43497 | CACNA1G | Voltage-dependent T-type calcium channel subunit alpha-1G | inhibitor | targets |
| O95180 | CACNA1H | Voltage-dependent T-type calcium channel subunit alpha-1H | inhibitor | targets |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | inhibitor | targets |
| Q00975 | CACNA1B | Voltage-dependent N-type calcium channel subunit alpha-1B | inhibitor | targets |
| Q06432 | CACNG1 | Voltage-dependent calcium channel | inhibitor | targets |
| Q12809 | KCNH2 | Voltage-gated inwardly rectifying potassium channel KCNH2 | inhibitor | targets |
| Q13936 | CACNA1C | Voltage-dependent L-type calcium channel subunit alpha-1C | inhibitor | targets |
| Q14654 | KCNJ11 | ATP-sensitive inward rectifier potassium channel 11 | inhibitor | targets |
| P31645 | SLC6A4 | Sodium-dependent serotonin transporter | unknown | targets |
| O15245 | SLC22A1 | Solute carrier family 22 member 1 | inhibitor | transporters |
| O15438 | ABCC3 | ATP-binding cassette sub-family C member 3 | inhibitor | transporters |
| O15439 | O15439 | ATP-binding cassette sub-family C member 4 | inhibitor | transporters |
| O76082 | O76082 | Organic cation/carnitine transporter 2 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | inhibitor | transporters |
| P33527 | ABCC1 | Multidrug resistance-associated protein 1 | inhibitor | transporters |
| P46721 | P46721 | Solute carrier organic anion transporter family member 1A2 | inhibitor | transporters |
| Q5T3U5 | Q5T3U5 | ATP-binding cassette sub-family C member 10 | inhibitor | transporters |
| Q86VL8 | SLC47A2 | Multidrug and toxin extrusion protein 2 | inhibitor | transporters |
| Q96FL8 | SLC47A1 | Multidrug and toxin extrusion protein 1 | inhibitor | transporters |
| Q9H015 | Q9H015 | Solute carrier family 22 member 4 | inhibitor | transporters |
| Q9Y6L6 | SLCO1B1 | Solute carrier organic anion transporter family member 1B1 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |