| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| September 27th, 2005 | 33 | Yes |
Popular Name: Verapamil Hydrochloride Verapamil Hydrochloride
Find On: PubMed — Wikipedia — Google
CAS Numbers: 152-11-4 , 152-11-4, 52-53-9 , 152-11-4, 52-53-9 [verapamil] , 152-11-4; 23313-68-0; 52-53-9 , 23313-68-0 , 23313-68-0;152-11-4 , 38321-02-7 , 52-53-9 , [152-11-4]
(1)-3-(3,4-Dimethoxyphenyl)-6-((5,6-dimethoxyphenethyl)methylamino)hexane-3-carbonitrile
(±)-Verapamil hydrochloride, 99+%
152-11-4; Prestwick_440; Verapamyl hydrochloride
2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
5-((3,4-dimethoxyphenethyl)(methyl)amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile
5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
52-53-9; D02356; Verapamil (USAN/INN)
alpha-((N-Methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
alpha-Isopropyl-alpha-((N-methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
C27H38N2O4.C24H34N2O5.Cl; LS-178657; TARKA; TRANDOLAPRIL; VERAPAMIL HYDROCHLORIDE
DIMETHOXYPHENYLDIMETHOXYPHENYLETHYLMETHYLAMINOISOPROPYLPENTANENITRIL
DIMETHOXYPHENYLDIMETHOXYPHENYLETHYLMETHYLAMINOISOPROPYLPENTANENITRILEHYDROCHLORID
Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-
Verapamil Hydrochloride (Isoptin, Iproveratril, Calan)
Verapamil Hydrochloride [23313-68-0]
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | 4.55 | 12.51 | -58.32 | 1 | 6 | 1 | 65 | 455.619 | 13 | ↓ |
| Hi High (pH 8-9.5) | 4.55 | 10.19 | -15.26 | 0 | 6 | 0 | 64 | 454.611 | 13 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| biological_use | Antiarrhythmic (class IV) agent | ZereneX Building Blocks |
| SOLUBILITY | .; methanol: 50 mg/mL, clear, colorless | Indofine |
| Mp [°C] | 140 - 144 | Acros Organics |
| MP | 142 - 144 | Enamine Building Blocks |
| M.P | 142 °C | Indofine |
| MP | 142...144 | Enamine Building Blocks |
| ALOGPS_SOLUBILITY | 3.94e-03 g/l | DrugBank-approved |
| purity | 9.500000000000000e+001 | Enamine Building Blocks Enamine Building Blocks |
| Purity | 95% | Fluorochem |
| Purity | 98% | Fluorochem |
| therap | adrenegic blocker, Ca channel blocker, coronary vasodilator, antiarrhythmic | MicroSource Spectrum |
| biological_use | Antiarrhythmic (class IV) agent | IBScreen Bioactives IBScreen Bioactives |
| mechanism | Calcium antagonist | IBScreen Bioactives IBScreen Bioactives |
| Target | Calcium Channel | Selleck Chemicals |
| Notes | Calcium channel blocker | Apollo Scientific Bioactives |
| biological_use | Coronary vasodilator | IBScreen Bioactives |
| H phrase | H301: Toxic if swallowed | Acros Organics |
| H phrase | H301: Toxic if swallowed; H331: Toxic if inhaled; H311: Toxic in contact with skin | Acros Organics |
| mechanism | Inhibits movement of calcium ions across the cell membrane | IBScreen Bioactives |
| Warnings | IRRITANT | Matrix Scientific |
| Therapy | L-type Ca2+ channel modulator; adrenoceptor antagonist; antiarryhthmic; cardiac depressant; coronary vasodilator | SMDC Iconix |
| PUBCHEM_SUBSTANCE_COMMENT | NCC_SAMPLE_SUPPLIER : Tocris Cookson Ltd.; NCC_SUPPLIER_STRUCTURE_ID : 101617; .5 water; 1 hydrogen chloride | NIH Clinical Collection via PubChem |
| Target | Others | Selleck Chemicals |
| P phrase | P301 + P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician | Acros Organics |
| P phrase | P301 + P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician; P280: Wear protective gloves/protective clothing/eye protection/face protection; P312: Call a POISON CENTER or doctor/physician if you feel unwell; P302 + P350: IF ON SKIN: G | Acros Organics |
| mechanism | Protein kinase C inhibitor | IBScreen Bioactives |
| R phrase | R23/24/25: Toxic by inhalation, in contact with skin and if swallowed. | Acros Organics |
| S phrase | S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. | Acros Organics |
| S phrase | S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.; S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). | Acros Organics |
| PUBCHEM_SUBSTANCE_COMMENT | SAMPLE_SUPPLIER: Tocris Bioscience; SUPPLIER_STRUCTURE_ID: 101617; SALT: .5 water; 1 hydrogen chloride | NIH Clinical Collection via PubChem |
| biological_use | Smooth muscle relaxant. | IBScreen Bioactives |
| Hazard | T: Toxic | Acros Organics |
| biological_use | Used in the treatment of hypertension, angina pectoris, cardiac arrhythmia, and cluster headaches. | IBScreen Bioactives |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| CAC1C-1-E | Voltage-gated L-type Calcium Channel Alpha-1C Subunit (cluster #1 Of 1), Eukaryotic | Eukaryotes | 38 | 0.31 | Binding ≤ 10μM |
| CAC1D-2-E | Voltage-gated L-type Calcium Channel Alpha-1D Subunit (cluster #2 Of 2), Eukaryotic | Eukaryotes | 38 | 0.31 | Binding ≤ 10μM |
| CAC1S-1-E | Voltage-gated L-type Calcium Channel Alpha-1S Subunit (cluster #1 Of 1), Eukaryotic | Eukaryotes | 58 | 0.31 | Binding ≤ 10μM |
| KCNH2-5-E | HERG (cluster #5 Of 5), Eukaryotic | Eukaryotes | 6850 | 0.22 | Binding ≤ 10μM |
| MDR1-1-E | P-glycoprotein 1 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 9800 | 0.21 | Binding ≤ 10μM |
| MRP1-1-E | Multidrug Resistance-associated Protein 1 (cluster #1 Of 1), Eukaryotic | Eukaryotes | 9660 | 0.21 | Binding ≤ 10μM |
| P97706-1-E | Sodium Channel Protein Type VI Alpha Subunit (cluster #1 Of 1), Eukaryotic | Eukaryotes | 2500 | 0.24 | Binding ≤ 10μM |
| S22A1-1-E | Solute Carrier Family 22 Member 1 (cluster #1 Of 1), Eukaryotic | Eukaryotes | 6800 | 0.22 | Binding ≤ 10μM |
| SCN1A-1-E | Sodium Channel Protein Type I Alpha Subunit (cluster #1 Of 2), Eukaryotic | Eukaryotes | 3300 | 0.23 | Binding ≤ 10μM |
| SCN2A-1-E | Sodium Channel Protein Type II Alpha Subunit (cluster #1 Of 2), Eukaryotic | Eukaryotes | 3300 | 0.23 | Binding ≤ 10μM |
| SCN3A-1-E | Sodium Channel Protein Type III Alpha Subunit (cluster #1 Of 2), Eukaryotic | Eukaryotes | 3300 | 0.23 | Binding ≤ 10μM |
| SCN5A-1-E | Sodium Channel Protein Type V Alpha Subunit (cluster #1 Of 1), Eukaryotic | Eukaryotes | 2500 | 0.24 | Binding ≤ 10μM |
| SCN8A-1-E | Sodium Channel Protein Type VIII Alpha Subunit (cluster #1 Of 2), Eukaryotic | Eukaryotes | 3300 | 0.23 | Binding ≤ 10μM |
| TSPO-1-E | Peripheral-type Benzodiazepine Receptor (cluster #1 Of 1), Eukaryotic | Eukaryotes | 1 | 0.38 | Binding ≤ 10μM |
| CAC1C-1-E | Voltage-gated L-type Calcium Channel Alpha-1C Subunit (cluster #1 Of 1), Eukaryotic | Eukaryotes | 38 | 0.31 | Functional ≤ 10μM |
| CAC1D-1-E | Voltage-gated L-type Calcium Channel Alpha-1D Subunit (cluster #1 Of 1), Eukaryotic | Eukaryotes | 38 | 0.31 | Functional ≤ 10μM |
| KCNH2-1-E | HERG (cluster #1 Of 2), Eukaryotic | Eukaryotes | 143 | 0.29 | Functional ≤ 10μM |
| MDR1-1-E | P-glycoprotein 1 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 6300 | 0.22 | Functional ≤ 10μM |
| MDR3-1-E | P-glycoprotein 3 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 10000 | 0.21 | Functional ≤ 10μM |
| P97706-1-E | Sodium Channel Protein Type VI Alpha Subunit (cluster #1 Of 1), Eukaryotic | Eukaryotes | 2500 | 0.24 | Functional ≤ 10μM |
| SCN5A-1-E | Sodium Channel Protein Type V Alpha Subunit (cluster #1 Of 1), Eukaryotic | Eukaryotes | 2500 | 0.24 | Functional ≤ 10μM |
| CP3A4-2-E | Cytochrome P450 3A4 (cluster #2 Of 4), Eukaryotic | Eukaryotes | 6460 | 0.22 | ADME/T ≤ 10μM |
| Z50425-11-O | Plasmodium Falciparum (cluster #11 Of 22), Other | Other | 800 | 0.26 | Functional ≤ 10μM |
| Z50425-11-O | Plasmodium Falciparum (cluster #11 Of 22), Other | Other | 3162 | 0.23 | Functional ≤ 10μM |
| Z50512-1-O | Cavia Porcellus (cluster #1 Of 7), Other | Other | 800 | 0.26 | Functional ≤ 10μM |
| Z50592-3-O | Oryctolagus Cuniculus (cluster #3 Of 8), Other | Other | 300 | 0.28 | Functional ≤ 10μM |
| Z50597-1-O | Rattus Norvegicus (cluster #1 Of 12), Other | Other | 47 | 0.31 | Functional ≤ 10μM |
| Z80133-1-O | EMT6 (Mammary Carcinoma Cells) (cluster #1 Of 3), Other | Other | 5800 | 0.22 | Functional ≤ 10μM |
| Z80224-1-O | MCF7 (Breast Carcinoma Cells) (cluster #1 Of 14), Other | Other | 53 | 0.31 | Functional ≤ 10μM |
| Z80232-1-O | MCF7-VP (cluster #1 Of 1), Other | Other | 12 | 0.34 | Functional ≤ 10μM |
| Z80362-1-O | P388 (Lymphoma Cells) (cluster #1 Of 8), Other | Other | 3100 | 0.23 | Functional ≤ 10μM |
| Z80364-1-O | P388/ADR (Lymphoma Cells) (cluster #1 Of 1), Other | Other | 5 | 0.35 | Functional ≤ 10μM |
| Z80532-1-O | T-24 (Bladder Carcinoma Cells) (cluster #1 Of 6), Other | Other | 7 | 0.35 | Functional ≤ 10μM |
| Z80711-1-O | NCI/ADR-RES (Breast Carcinoma Cells) (cluster #1 Of 2), Other | Other | 6 | 0.35 | Functional ≤ 10μM |
| Z80773-1-O | CHRC/5 Cell Line (cluster #1 Of 1), Other | Other | 3000 | 0.23 | Functional ≤ 10μM |
| Z80774-1-O | CHRC5 Cell Line (cluster #1 Of 1), Other | Other | 1200 | 0.25 | Functional ≤ 10μM |
| Z80928-6-O | HCT-116 (Colon Carcinoma Cells) (cluster #6 Of 9), Other | Other | 500 | 0.27 | Functional ≤ 10μM |
| Z81008-1-O | Human Breast Cancer Cell Lines (cluster #1 Of 1), Other | Other | 2400 | 0.24 | Functional ≤ 10μM |
| Z81245-1-O | MDA-MB-435 (Breast Carcinoma Cells) (cluster #1 Of 6), Other | Other | 700 | 0.26 | Functional ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| KCNH2_HUMAN | Q12809 | HERG, Human | 141.253754 | 0.29 | Binding ≤ 1μM |
| MRP1_HUMAN | P33527 | Multidrug Resistance-associated Protein 1, Human | 35 | 0.32 | Binding ≤ 1μM |
| MDR1_HUMAN | P08183 | P-glycoprotein 1, Human | 300 | 0.28 | Binding ≤ 1μM |
| TSPO_RAT | P16257 | Peripheral-type Benzodiazepine Receptor, Rat | 1.4 | 0.38 | Binding ≤ 1μM |
| CAC1C_RABIT | P15381 | Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Rabit | 1000 | 0.25 | Binding ≤ 1μM |
| CAC1C_HUMAN | Q13936 | Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Human | 150 | 0.29 | Binding ≤ 1μM |
| CAC1C_RAT | P22002 | Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Rat | 3.7 | 0.36 | Binding ≤ 1μM |
| CAC1D_HUMAN | Q01668 | Voltage-gated L-type Calcium Channel Alpha-1D Subunit, Human | 38 | 0.31 | Binding ≤ 1μM |
| CAC1D_RAT | P27732 | Voltage-gated L-type Calcium Channel Alpha-1D Subunit, Rat | 3.7 | 0.36 | Binding ≤ 1μM |
| CAC1S_RAT | Q02485 | Voltage-gated L-type Calcium Channel Alpha-1S Subunit, Rat | 58 | 0.31 | Binding ≤ 1μM |
| KCNH2_HUMAN | Q12809 | HERG, Human | 141.253754 | 0.29 | Binding ≤ 10μM |
| MRP1_HUMAN | P33527 | Multidrug Resistance-associated Protein 1, Human | 35 | 0.32 | Binding ≤ 10μM |
| MDR1_HUMAN | P08183 | P-glycoprotein 1, Human | 1041 | 0.25 | Binding ≤ 10μM |
| TSPO_RAT | P16257 | Peripheral-type Benzodiazepine Receptor, Rat | 1.4 | 0.38 | Binding ≤ 10μM |
| SCN1A_HUMAN | P35498 | Sodium Channel Protein Type I Alpha Subunit, Human | 3300 | 0.23 | Binding ≤ 10μM |
| SCN2A_HUMAN | Q99250 | Sodium Channel Protein Type II Alpha Subunit, Human | 3300 | 0.23 | Binding ≤ 10μM |
| SCN3A_HUMAN | Q9NY46 | Sodium Channel Protein Type III Alpha Subunit, Human | 3300 | 0.23 | Binding ≤ 10μM |
| SCN5A_RAT | P15389 | Sodium Channel Protein Type V Alpha Subunit, Rat | 2500 | 0.24 | Binding ≤ 10μM |
| P97706_RAT | P97706 | Sodium Channel Protein Type VI Alpha Subunit, Rat | 2500 | 0.24 | Binding ≤ 10μM |
| SCN8A_HUMAN | Q9UQD0 | Sodium Channel Protein Type VIII Alpha Subunit, Human | 3300 | 0.23 | Binding ≤ 10μM |
| S22A1_HUMAN | O15245 | Solute Carrier Family 22 Member 1, Human | 6800 | 0.22 | Binding ≤ 10μM |
| CAC1C_RAT | P22002 | Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Rat | 3.7 | 0.36 | Binding ≤ 10μM |
| CAC1C_HUMAN | Q13936 | Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Human | 150 | 0.29 | Binding ≤ 10μM |
| CAC1C_RABIT | P15381 | Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Rabit | 1000 | 0.25 | Binding ≤ 10μM |
| CAC1D_RAT | P27732 | Voltage-gated L-type Calcium Channel Alpha-1D Subunit, Rat | 3.7 | 0.36 | Binding ≤ 10μM |
| CAC1D_HUMAN | Q01668 | Voltage-gated L-type Calcium Channel Alpha-1D Subunit, Human | 38 | 0.31 | Binding ≤ 10μM |
| CAC1S_RAT | Q02485 | Voltage-gated L-type Calcium Channel Alpha-1S Subunit, Rat | 58 | 0.31 | Binding ≤ 10μM |
| Z50512 | Z50512 | Cavia Porcellus | 100 | 0.30 | Functional ≤ 10μM |
| Z80773 | Z80773 | CHRC/5 Cell Line | 3000 | 0.23 | Functional ≤ 10μM |
| Z80774 | Z80774 | CHRC5 Cell Line | 1200 | 0.25 | Functional ≤ 10μM |
| Z80133 | Z80133 | EMT6 (Mammary Carcinoma Cells) | 5800 | 0.22 | Functional ≤ 10μM |
| Z80928 | Z80928 | HCT-116 (Colon Carcinoma Cells) | 130 | 0.29 | Functional ≤ 10μM |
| KCNH2_HUMAN | Q12809 | HERG, Human | 143 | 0.29 | Functional ≤ 10μM |
| Z81008 | Z81008 | Human Breast Cancer Cell Lines | 1200 | 0.25 | Functional ≤ 10μM |
| Z80224 | Z80224 | MCF7 (Breast Carcinoma Cells) | 0.1 | 0.42 | Functional ≤ 10μM |
| Z80232 | Z80232 | MCF7-VP | 0.2 | 0.41 | Functional ≤ 10μM |
| Z81245 | Z81245 | MDA-MB-435 (Breast Carcinoma Cells) | 0.25 | 0.41 | Functional ≤ 10μM |
| Z80711 | Z80711 | NCI/ADR-RES (Breast Carcinoma Cells) | 0.6 | 0.39 | Functional ≤ 10μM |
| Z50592 | Z50592 | Oryctolagus Cuniculus | 300 | 0.28 | Functional ≤ 10μM |
| MDR1_HUMAN | P08183 | P-glycoprotein 1, Human | 120 | 0.29 | Functional ≤ 10μM |
| MDR1_MOUSE | P06795 | P-glycoprotein 1, Mouse | 2000 | 0.24 | Functional ≤ 10μM |
| MDR3_MOUSE | P21447 | P-glycoprotein 3, Mouse | 10000 | 0.21 | Functional ≤ 10μM |
| Z80362 | Z80362 | P388 (Lymphoma Cells) | 3100 | 0.23 | Functional ≤ 10μM |
| Z80364 | Z80364 | P388/ADR (Lymphoma Cells) | 0.1 | 0.42 | Functional ≤ 10μM |
| Z50425 | Z50425 | Plasmodium Falciparum | 1000 | 0.25 | Functional ≤ 10μM |
| Z50597 | Z50597 | Rattus Norvegicus | 10 | 0.34 | Functional ≤ 10μM |
| SCN5A_RAT | P15389 | Sodium Channel Protein Type V Alpha Subunit, Rat | 2500 | 0.24 | Functional ≤ 10μM |
| P97706_RAT | P97706 | Sodium Channel Protein Type VI Alpha Subunit, Rat | 2500 | 0.24 | Functional ≤ 10μM |
| Z80532 | Z80532 | T-24 (Bladder Carcinoma Cells) | 0.5 | 0.39 | Functional ≤ 10μM |
| CAC1C_HUMAN | Q13936 | Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Human | 38 | 0.31 | Functional ≤ 10μM |
| CAC1C_RAT | P22002 | Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Rat | 1.4 | 0.38 | Functional ≤ 10μM |
| CAC1D_HUMAN | Q01668 | Voltage-gated L-type Calcium Channel Alpha-1D Subunit, Human | 38 | 0.31 | Functional ≤ 10μM |
| CAC1D_RAT | P27732 | Voltage-gated L-type Calcium Channel Alpha-1D Subunit, Rat | 1.4 | 0.38 | Functional ≤ 10μM |
| CP3A4_HUMAN | P08684 | Cytochrome P450 3A4, Human | 4700 | 0.23 | ADME/T ≤ 10μM |
| Description | Species |
|---|---|
| Abacavir transmembrane transport | |
| ABC-family proteins mediated transport | |
| Adrenaline,noradrenaline inhibits insulin secretion | |
| Aflatoxin activation and detoxification | |
| Cobalamin (Cbl, vitamin B12) transport and metabolism | |
| Interaction between L1 and Ankyrins | |
| Na+/Cl- dependent neurotransmitter transporters | |
| NCAM1 interactions | |
| Neurotransmitter Clearance In The Synaptic Cleft | |
| Norepinephrine Neurotransmitter Release Cycle | |
| Organic cation transport | |
| Regulation of insulin secretion | |
| Synthesis of Leukotrienes (LT) and Eoxins (EX) | |
| Voltage gated Potassium channels | |
| Xenobiotics |
