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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2D Structure
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Physico-chemical Properties
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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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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
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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
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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
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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]