verapamil   Click here for help

GtoPdb Ligand ID: 2406

Synonyms: Ansyr® | CP-165331 / CP-16533-1 | Securon®
Approved drug
verapamil is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: The approved drug verapamil is a racemic mixture of two enantiomers (PubChem CID 92305 and PubChem CID 65808). The structure shown here does not specify stereochemistry and represents the mixture. Marketed formulations may contain verapamil hydrochloride (PubChem CID 62969).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: verapamil

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 13
Topological polar surface area 63.95
Molecular weight 454.28
XLogP 4.97
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COc1ccc(cc1OC)CCN(CCCC(c1ccc(c(c1)OC)OC)(C(C)C)C#N)C
Isomeric SMILES COc1ccc(cc1OC)CCN(CCCC(c1ccc(c(c1)OC)OC)(C(C)C)C#N)C
InChI InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3
InChI Key SGTNSNPWRIOYBX-UHFFFAOYSA-N
Bioactivity Comments
Verapamil has been reported to improve the activity in vitro of bedaquiline against Mycobacterium tuberculosis and Mycobacterium abscessus clinical isolates and may have clinical potential as an adjunctive therapy [5,11].
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Organic cation/carnitine transporter 1
Organic cation/carnitine transporter 2
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Cav1.4 Mm Channel blocker - - - 1x10-4 2
⤷ Conc range: 1x10-4 M [2]
Voltage: -80.0 mV
Kv1.7 Hs Channel blocker - 4.8 pKd - 1
⤷ pKd 4.8 [1]
Kv3.2 Rn Channel blocker - 4.9 pEC50 - 9
⤷ pEC50 4.9 [9]
Cav1.2 Primary target of this compound Rn Channel blocker Antagonist 5.3 – 6.5 pIC50 - 6
⤷ pIC50 5.3 – 6.5 [6]
Cav1.2 Rn Gating inhibitor Antagonist 5.3 – 6.5 pIC50 - 6
⤷ pIC50 5.3 – 6.5 [6]
Voltage: -60.0 – 10.0 mV
TPC2 Hs Channel blocker Inhibition 5.0 pIC50 - 14
⤷ pIC50 5.0 (IC50 1x10-5 M) [14]
Cav1.1 Primary target of this compound Oc Channel blocker Antagonist ~5.0 pIC50 - 12
⤷ pIC50 ~5.0 (IC50 ~1x10-5 M) [12]
Voltage: 100.0 mV
TPC1 Hs Channel blocker Inhibition 4.6 pIC50 - 3
⤷ pIC50 4.6 (IC50 2.3x10-5 M) [3]
Kv1.8 Hs Channel blocker - 4.3 pIC50 - 8
⤷ pIC50 4.3 [8]
Kir3.2 Mm Gating inhibitor Antagonist 3.9 pIC50 - 7
⤷ pIC50 3.9 [7]
Voltage: -100.0 mV
Cav1.3 Mm Channel blocker Antagonist 3.7 pIC50 - 10
⤷ pIC50 3.7 [10]
Voltage: -70.0 mV
Navi2.1 Hs Channel blocker - 3.4 pIC50 -
⤷ pIC50 3.4 (IC50 3.8x10-4 M)
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CYP3A4 Hs Inhibitor Inhibition 6.2 pKi - 15
⤷ pKi 6.2 (Ki 6x10-7 M) [15]
Description: Inhibition of testosterone 6β-hydroxylation.
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Plasma membrane monoamine transporter Hs Inhibitor Inhibition 4.7 pKi - 4,13
⤷ pKi 4.7 (Ki 1.86x10-5 M) [4,13]