Drug Information

General Information
Drug ID
DR00264
Drug Name
Verapamil
Synonyms
(+-)-Verapamil; (+/-)-VERAPAMIL; (1)-3-(3,4-Dimethoxyphenyl)-6-((5,6-dimethoxyphenethyl)methylamino)hexane-3-carbonitrile; 2-(3,4-Dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methyl-amino]-2-(1-methylethyl) pentanenitrile; 2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile; 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile; 5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile; 5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile; Alpha-((N-Methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile; Alpha-(3-((2-(3,4-Dimethoxyphenyl)ethyl)-methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile; Alpha-Isopropyl-alpha-((N-methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile; Arpamyl; Bosoptin (TN); CP-16533-1; Calan; Calan (TN); Calcan; Cordilox; Covera-HS (TN); D-365; Dexverapamil; Dilacoran; Drosteakard; Iproveratril; Isoptimo; Isoptin; Isoptin (TN); Isotopin; Vasolan; Veracim; Verapamil (Na-Ca chanel blocker); Verapamil (USAN/INN); Verapamil [USAN:BAN:INN]; Verapamil [USAN:INN:BAN]; Verapamilo; Verapamilo [INN-Spanish]; Verapamilum; Verapamilum [INN-Latin]; Veraptin; Verelan (TN); Verexamil
Drug Type
Small molecular drug
Indication Angina [ICD11:BA40] Approved [1]
High blood pressure [ICD11:BA00] Approved [1]
Therapeutic Class
Analgesics
Structure
3D MOL 2D MOL
Formula
C27H38N2O4
Canonical SMILES
CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
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
InChIKey
SGTNSNPWRIOYBX-UHFFFAOYSA-N
CAS Number
CAS 52-53-9
Pharmaceutical Properties Molecular Weight 454.6 Topological Polar Surface Area 64
Heavy Atom Count 33 Rotatable Bond Count 13
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
XLogP
3.8
PubChem CID
2520
PubChem SID
10525256 ,11120305 ,11120793 ,11121281 ,11121578 ,11122058 ,11335574 ,11360813 ,11362647 ,11364755 ,11365209 ,11367317 ,11367771 ,11369879 ,11370565 ,11370566 ,11372920 ,11373372 ,11374511 ,11375479 ,11375933 ,11378044 ,11424501 ,11461785 ,11466169 ,11467289 ,11485556 ,11485917 ,11489556 ,11492721 ,14784349 ,26751824 ,26751825 ,29221683 ,3153219 ,46508158 ,47217025 ,47291346 ,47291347 ,47440510 ,47515567 ,47589211 ,47885631 ,48035377 ,5635244 ,598709 ,7849415 ,7980877 ,8151673 ,9397
ChEBI ID
ChEBI:9948
TTD Drug ID
D0R0FE
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
MDR3 Transporter Info Multidrug resistance protein 3 Substrate [3]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [4]
OCTN1 Transporter Info Organic cation/carnitine transporter 1 Substrate [5]
OCTN2 Transporter Info Organic cation/carnitine transporter 2 Substrate [6]
P-GP Transporter Info P-glycoprotein 1 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data P-GP Transporter Info Km =4.06 microM High five cells-MDR1 [8]
P-GP Transporter Info Km =24 microM Madin-Darby canine kidney cells (MDCKII)-MDR1 [9]
P-GP Transporter Info Km =2 microM Spodoptera frugiperda (Sf9) cells-MDR1 [10]
P-GP Transporter Info Km =4.1 microM Spodoptera frugiperda (Sf9) cells-MDR1 [11]
References
1 Verapamil was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Implications of genetic polymorphisms in drug transporters for pharmacotherapy. Cancer Lett. 2006 Mar 8;234(1):4-33.
3 MDR3 P-glycoprotein, a phosphatidylcholine translocase, transports several cytotoxic drugs and directly interacts with drugs as judged by interference with nucleotide trapping. J Biol Chem. 2000 Aug 4;275(31):23530-9.
4 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
5 Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73.
6 Genetic variations of the SLC22A5 gene in the Chinese and Indian populations of Singapore. Drug Metab Pharmacokinet. 2010;25(1):112-9.
7 Improved expression and purification of human multidrug resistance protein MDR1 from baculovirus-infected insect cells. Protein Expr Purif. 2009 Jul;66(1):7-14.
8 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
9 Chalcogenopyrylium compounds as modulators of the ATP-binding cassette transporters P-glycoprotein (P-gp/ABCB1) and multidrug resistance protein 1 (MRP1/ABCC1). J Med Chem. 2012 May 24;55(10):4683-99.
10 Synthesis and evaluation of 3D templates based on a taxane skeleton to circumvent P-glycoprotein-associated multidrug resistance of cancer. Bioorg Med Chem Lett. 2005 May 16;15(10):2601-5.
11 Modulation of drug-stimulated ATPase activity of human MDR1/P-glycoprotein by cholesterol. Biochem J. 2007 Jan 15;401(2):597-605.

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