2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

• ChemBase ID: 543
• Molecular Formular: C27H38N2O4
• Molecular Mass: 454.60162
• Monoisotopic Mass: 454.28315771
• SMILES: O(c1cc(C(C(C)C)(CCCN(CCc2cc(OC)c(OC)cc2)C)C#N)ccc1OC)C
• Canonical 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
• InChIKey: SGTNSNPWRIOYBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
• IUPAC Traditional name: 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile; verapamil; veraβ
• Brand Name: Apo-Verap; Arpamyl; Berkatens; Calan; Calan SR; Cardiagutt; Cardibeltin; Cordilox; Covera-HS; Dignover; Dilacoran; Drosteakard; Geangin; Iproveratril; Isoptimo; Isoptin; Isoptin SR; Novo-Veramil; NU-Verap; Quasar; Securon; Univer; Vasolan; Veracim; Veramex; Veraptin; Verelan; Verelan PM; Verexamil
• Synonyms: Berkatens; Calan; Cordilox; Covera; Ethimil; Geangin; Securon; Univer; Vasolan; Verapress; Verelan; Verapamil; Verapamil HCl; Verapamilo [INN-Spanish]; Verapamilum [INN-Latin]; Verapamil; Verapamil [Usan:Ban:Inn]; Isoptin; 5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-Dimethoxyphenyl)-2-isopropylvaleronitrile; Iproveratril; (±)-VERAPAMIL HYDROCHLORIDE

Database IDs

• CAS Number: 52-53-9; 152-11-4
• EC Number: 205-800-5
• PubChem SID: 160964006; 46508158
• PubChem CID: 2520
• CHEBI ID: 9948
• ATC CODE: C08DA01
• CHEMBL: 6966
• Chemspider ID: 2425
• DrugBank ID: DB00661
• IUPHAR ligand ID: 2406
• KEGG ID: D02356
• Unique Ingredient Identifier: CJ0O37KU29
• Wikipedia Title: Verapamil

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.6246759
• LogD (pH = 7.4): 2.7877045
• Log P: 5.0431857
• Molar Refractivity: 132.6479 cm^3
• Polarizability: 51.54108 Å^3
• Polar Surface Area: 63.95 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.23
• LOG S: -5.06
• Solubility (Water): 3.94e-03 g/l

PROPERTIES

Physical Property

• Solubility: 4.47 mg/L
• Melting Point: 140-150 °C
• Hydrophobicity(logP): 4.7

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: YV8320000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:25
• Safety Statements: S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

Pharmacology Properties

• Admin Routes: Oral, Intravenous
• Bioavailability: 35.1%
• Excretion: Renal: 11%
• Half Life: 2.8-7.4 hours
• Metabolism: Hepatic
• Legal Status: Rx-only
• Pregnancy Category: C (US)
• US Licence: Verapamil
• Mechanism of Action: Calcium antagonist; Inhibits movement of calcium ions across the cell membrane; Protein kinase C inhibitor

Product Information

• Application(s): Antiarrhythmic (class IV) agent; Coronary vasodilator; Smooth muscle relaxant.; Used in the treatment of hypertension, angina pectoris, cardiac arrhythmia, and cluster headaches.

DETAILS

MP Biomedicals - 02195545

Hydrochloride
α₁ -Antagonist and calcium channel modulator.

DrugBank - DB00661

• Drug Groups: approved
• Description: A calcium channel blocker that is a class IV anti-arrhythmia agent. [PubChem]
• Indication: For the treatment of hypertension, angina, and cluster headache prophylaxis.
• Pharmacology: Verapamil is an L-type calcium channel blocker that also has antiarrythmic activity. The R-enantiomer is more effective at reducing blood pressure compared to the S-enantiomer. However, the S-enantiomer is 20 times more potent than the R-enantiomer at prolonging the PR interval in treating arrhythmias.
• Toxicity: LD₅₀=8 mg/kg (i.v. in mice)
• Affected Organisms: Humans and other mammals
• Absorption: 90%
• Half Life: 2.8-7.4 hours
• Protein Binding: 90%
• Elimination: Approximately 70% of an administered dose is excreted as metabolites in the urine and 16% or more in the feces within 5 days. About 3% to 4% is excreted in the urine as unchanged drug.
• References: Bellamy WT: P-glycoproteins and multidrug resistance. Annu Rev Pharmacol Toxicol. 1996;36:161-83. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

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