Drug Details

General Information of the Drug (ID: DR5795)
Name
Verapamil
Synonyms
VERAPAMIL; 52-53-9; Iproveratril; Vasolan; Dilacoran; Isoptin; Falicard; Finoptin; Isoptine; Calan; Lekoptin; Verapamilo; Verapamilum; Isotopin; Securon; Verelan; Calcan; Tarka; D-365; Cardibeltin; Izoptin; CP-16533-1; Covera-HS; Verpamil; Verelan PM; 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; Cardiagutt; Berkatens; Dignover; Geangin; Veramex; Quasar; Univer; 5-((3,4-dimethoxyphenethyl)(methyl)amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile; Novo-Veramil; Apo-Verap; Isoptin SR; Nu-Verap; Calan SR; Isoptimo; Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-; (+/-)-Verapamil hydrochlorid; CHEBI:77733; Cardiabeltin; Cardioprotect; Durasoptin; Hexasoptin; Veratensin; Veroptinstada; Calaptin; Caveril; Civicor; Coraver; Corpamil; Harteze; Hormitol; Ikapress; Inselon; Isoptino; Jenapamil; Lodixal; Magotiron; Praecicor; Robatelan; Vasomil; Vasopten; Verabeta; Veracor; Verahexal; Veraloc; Veramil; Verapin; Verasal; Verasifar; Verdilac; Vetrimil; Akilen; Elthon; Flamon; Ikacor; Univex; Vortac; Anpec; Ormil; Rapam; Civicor Retard; Isoptin Retard; Manidon Retard; Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-; Vera-Sanorania; Verapamil Acis; Verapamil Atid; Verapamil Ebewe; Verapamil Riker; Verapamil Verla; (+/-)-Verapamil;CP-16533-1; Benzeneacetonitrile, .alpha.-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-.alpha.-(1-methylethyl)-; Verapamil Basics; Verapamil Nordic; Verapamil-AbZ; Novapamyl LP; Verapamil AL; Verapamil NM; Verapamil PB; Verapamil SR; Cordilox SR; Dilacoran HTA; Veracaps SR; Verapamil MSD; Verapamilum [INN-Latin]; Arpamyl LP; Hexasoptin Retard; Verapamil Henning; Verelan SR; NCGC00016083-09; Verapamilo [INN-Spanish]; 2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile; Verapamil Injection; CP-16,533-1; Verapamil NM Pharma; Calaptin 240 SR; Verapress 240 SR; 5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile; DSSTox_CID_21152; DSSTox_RID_79636; DSSTox_GSID_41152; (+/-)-VERAPAMIL; Verapamil [USAN:INN:BAN]; dl-Verapamil; r,s-verapamil; CAS-52-53-9; CCRIS 6749; NSC272366; Verapamil (USAN/INN); EINECS 200-145-1; Ansyr; NSC 272306NA; EINECS 260-462-6; Calan (Salt/Mix); Akilen (Salt/Mix); alpha-((N-Methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile; Isoptin (Salt/Mix); 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; Cordilox (Salt/Mix); delta-365; Covera-HS (Salt/Mix); Prestwick0_000141; Prestwick1_000141; Prestwick2_000141; Prestwick3_000141; Spectrum2_001740; Spectrum4_000906; Spectrum5_001786; CP 16533-1; D 365; CHEMBL6966; Lopac0_001237; SCHEMBL16742; BSPBio_000242; BSPBio_001513; BSPBio_002358; KBioGR_000233; KBioGR_001372; KBioGR_002343; KBioSS_000233; KBioSS_002346; 56949-77-0; Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino) propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-; MLS006011414; DivK1c_000399; SPBio_001820; SPBio_002181; BPBio1_000268; GTPL2406; CP 16533-1 (Verapamil); DTXSID9041152; SCHEMBL13287282; (A+/-)-Verapamil hydrochloride; BDBM81939; HSDB 3928; KBio1_000399; KBio2_000233; KBio2_002343; KBio2_002801; KBio2_004911; KBio2_005369; KBio2_007479; KBio3_000465; KBio3_000466; KBio3_002823; cMAP_000023; NINDS_000399; NSC-272306NA; Bio1_000425; Bio1_000914; Bio1_001403; Bio2_000233; Bio2_000713; HMS1791L15; HMS1989L15; HMS2089H17; HMS3402L15; Tox21_110300; NSC_62969; STK538085; AKOS005468962; Tox21_110300_1; CCG-205311; DB00661; MCULE-3016077278; SDCCGSBI-0051204.P005; CAS_52-53-9; IDI1_000399; IDI1_033983; NCGC00016083-04; NCGC00016083-05; NCGC00016083-06; NCGC00016083-07; NCGC00016083-08; NCGC00016083-10; NCGC00016083-11; NCGC00016083-13; NCGC00016083-14; NCGC00016083-15; NCGC00016083-16; NCGC00016083-17; NCGC00016083-18; NCGC00016083-20; NCGC00016083-25; NCGC00016083-34; NCGC00024710-04; NCGC00024710-05; NCGC00024710-06; NCGC00024710-07; NCGC00024710-08; NCGC00024710-09; NCGC00344584-01; 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-methyl-amino]-2-isopropyl-pentanenitrile; AC-16016; BP-21223; HY-14275; NCI60_020143; SMR001550201; SBI-0051204.P003; CP-165331; AB00053495; CS-0002967; FT-0603225; FT-0675801; ST50826367; 1394-EP2270011A1; 1394-EP2272841A1; 1394-EP2272972A1; 1394-EP2272973A1; 1394-EP2275420A1; 1394-EP2277865A1; 1394-EP2277872A1; 1394-EP2280008A2; 1394-EP2298742A1; 1394-EP2298764A1; 1394-EP2298765A1; 1394-EP2298776A1; 1394-EP2298779A1; 1394-EP2301923A1; 1394-EP2301931A1; 1394-EP2301936A1; 1394-EP2305648A1; 1394-EP2314585A1; 1394-EP2316832A1; 1394-EP2316833A1; 52V114; C07188; D02356; AB00053495-20; AB00053495_21; L001330; Q410291; BRD-A09533288-001-02-7; BRD-A09533288-003-05-6; CP-165331 / CP-16533-1; F2173-0851; VERAPAMIL, Dexverapamil, Verapamyl hydrochloride, VERAPAMIL HYDROCHLORIDE; .alpha.-((N-Methyl-N-homoveratryl)-.gamma.-aminopropyl)-3,4-dimethoxyphenylacetonitrile; (?)-alpha-[3-[[2-(3,4-Dimethoxyphenyl)ethyl](methyl)amino]propyl]-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile; 2-(3,4-Dimethoxyphenyl)-5-((2-(3,4-dimethoxyphenyl)ethyl)(methyl)amino)-2-isopropylpentanenitrile, (+/-)-; 2-(3,4-Dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]-2-isopropylpentanenitrile #; 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]methylamino}-2-(methy lethyl)pentanenitrile
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Molecular Type
Small molecule
Disease Hypertension [ICD-11: BA00] Approved [1]
Structure
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2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C27H38N2O4
PubChem CID
2520
Canonical SMILES
CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
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
ChEBI ID
CHEBI:77733
TTD Drug ID
D0R0FE
DrugBank ID
DB00661
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Trandolapril      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)		 A fixed-dose combination of trandolapril-verapamil seems to be an effective and safe option for the management of stage 2 hypertension in Mexican patients uncontrolled by monotherapy.
    β. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Reserpine      Rauvolfia serpentina     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CD80  Molecule Info 
Pathway MAP
Up-regulation Expression HLA-DRB5  Molecule Info 
Pathway MAP
Up-regulation Expression KLRK1  Molecule Info 
Pathway MAP
                    In-vitro Model YAC-1 CVCL_2244 Mouse lymphoma Mus musculus
B16-F10 CVCL_0159 Mouse melanoma Mus musculus
                    In-vivo Model For a xenograft model, Female C57BL/6 mice, 6-8 weeks of age, 18-20 g, were subcutaneously (s.c.) immunized in the abdominal region with 2x105, 5x105 or 1x106 B16F10 cells.
                    Experimental
                    Result(s)		 The B16F10 tumor cell vaccine treated with MIP in combination with RP and VP was safe and efficient.
Target and Pathway
Target(s) Calcium channel alpha-1G (CACNA1G)  Molecule Info  [4]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 Calcium signaling pathway
3 Circadian entrainment
4 Type II diabetes mellitus
Panther Pathway Endogenous cannabinoid signaling Click to Show/Hide
2 GABA-B receptor II signaling
3 Nicotine pharmacodynamics pathway
Pathwhiz Pathway Muscle/Heart Contraction Click to Show/Hide
Pathway Interaction Database Regulation of nuclear beta catenin signaling and target gene transcription Click to Show/Hide
Reactome NCAM1 interactions Click to Show/Hide
WikiPathways NCAM signaling for neurite out-growth Click to Show/Hide
2 Nicotine Activity on Chromaffin Cells
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2406).
Reference 2 Efficacy of a fixed-dose combination of trandolapril-verapamil in patients with stage 2 hypertension inadequately controlled by monotherapy. Clin Drug Investig. 2005;25(7):445-51.
Reference 3 Antitumor efficacy induced by a B16F10 tumor cell vaccine treated with mitoxantrone alone or in combination with reserpine and verapamil in mice. Exp Ther Med. 2011 Sep;2(5):911-916.
Reference 4 Mechanism of tissue-selective drug action in the cardiovascular system. Mol Interv. 2005 Apr;5(2):84-93.
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