Basic information
- CAS
38321-02-7- Standard SMILES
COc1ccc(CCN(C)CCC[C@](C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC- InChIKey
SGTNSNPWRIOYBX-HHHXNRCGSA-N- Molecular formula
- C27H38N2O4
- Average molar mass
- 454.6 g/mol
- Monoisotopic mass
- 454.2831577
Overview
Dexverapamil is a 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile that has R configuration. It competitively inhibits the multidrug resistance efflux pump P-glycoprotein (MDR-1, EC 3.6.3.44), thereby potentially increasing the effectiveness of a wide range of antineoplastic drugs which are inactivated by MDR-1 mechanisms. Dexverapamil exhibits lower calcium antagonistic activity and toxicity than racemic verapamil. It has a role as an EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor. It is a conjugate base of a dexverapamil(1+). It is an enantiomer of a (S)-verapamil.
Names & identifiers
- Preferred name
- Dexverapamil
- IUPAC
- (2R)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
- English name
- (+)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile
- Molecular formula
- C27H38N2O4
- Molecular weight
- 454.61
Names & synonyms
Dexverapamil38321-02-7(R)-verapamilDexverapamiloDexverapamilum(+)-verapamil(R)-(+)-verapamild-verapamil(+)-(R)-verapamilVerapamil, (r)-QR5PYD126V(2R)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
Show more names
DexverapamiDexverapamil Hydrochloride[R,(+)]-2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-(N-methyl-3,4-dimethoxyphenethylamino)valeronitrile(R)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)benzeneacetonitrile(aR)-a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-benzeneacetonitrile(αR)-α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl](methyl)amino]propyl]-3,4-dimethoxy-α-(1-methylethyl)benzeneacetonitrileBenzeneacetonitrile, a-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-, (R)-Benzeneacetonitrile, α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-, (αR)-
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 64 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 13
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 606
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Calcium Channel Blockers; Antiarrhythmics; Vasodilator Agents
Physicochemical properties
- Melting point
- 129 · 129-131°C
- Boiling point
- 586.1 · 586.1±50.0 °C(Predicted)
- Density
- 1.058 · 1.058±0.06 g/cm3(Predicted)
- pka
- 8.97 · 8.97±0.50(Predicted)
- FDA UNII
- 5 PYD126V · QR5PYD126V
- NCI Drug Dictionary
- dexverapamil
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
Metabolism/MetabolitesDexverapamil has known human metabolites that include (2R)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(4-hydroxy-3-methoxyphenyl)-2-(propan-2-yl)pentanenitrile, (R)-D-617, arverapamil, and 2-(3,4-dimethoxyphenyl)acetaldehyde.
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Drugs used to cause dilation of the blood vessels.
Applications
UsesBoth isomers inhibit the p-glycoprotein efflux pump in multidrug resistant tumor cells
Suppliers10 total
湖北瑞玛标物科技有限公司15787879035 15787875101 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
Related reactions
0 records
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Compound notes
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