verapamil   

GtoPdb Ligand ID: 2406

Synonyms: Ansyr® | CP-165331 / CP-16533-1 | Securon®
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
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1981))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
International Nonproprietary Names
INN number INN
2122 verapamil
Synonyms
Ansyr® | CP-165331 / CP-16533-1 | Securon®
Database Links
BindingDB Ligand 50279753
CAS Registry No. 52-53-9
ChEBI CHEBI:9948
ChEMBL Ligand CHEMBL6966
DrugBank Ligand DB00661
DrugCentral Ligand 2815
GtoPdb PubChem SID 135651305
PubChem CID 2520
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Wikipedia Verapamil