CHEBI:77734 - dexverapamil

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ChEBI Name dexverapamil
ChEBI ID CHEBI:77734
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H38N2O4
Net Charge 0
Average Mass 454.60160
Monoisotopic Mass 454.28316
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/t27-/m1/s1
InChIKey SGTNSNPWRIOYBX-HHHXNRCGSA-N
SMILES COc1ccc(CCN(C)CCC[C@@](C#N)(C(C)C)c2ccc(OC)c(OC)c2)cc1OC
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of xenobiotic-transporting ATPase (EC 3.6.3.44).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dexverapamil (CHEBI:77734) has role EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor (CHEBI:77748)
dexverapamil (CHEBI:77734) is a 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile (CHEBI:77733)
dexverapamil (CHEBI:77734) is conjugate base of dexverapamil(1+) (CHEBI:77737)
dexverapamil (CHEBI:77734) is enantiomer of (S)-verapamil (CHEBI:77736)
Incoming verapamil (CHEBI:9948) has part dexverapamil (CHEBI:77734)
dexverapamil(1+) (CHEBI:77737) is conjugate acid of dexverapamil (CHEBI:77734)
(S)-verapamil (CHEBI:77736) is enantiomer of dexverapamil (CHEBI:77734)
IUPAC Name
(2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
INNs Sources
dexverapamil WHO MedNet
dexvérapamil WHO MedNet
dexverapamilo WHO MedNet
dexverapamilum WHO MedNet
Synonyms Sources
(+)-(2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile ChEBI
(+)-(R)-5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile ChemIDplus
(+)-(R)-verapamil ChEBI
(+)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile ChEBI
(+)-3-(3,4-dimethoxyphenyl)-6-((5,6-dimethoxyphenethyl)methylamino)hexane-3-carbonitrile ChEBI
(+)-verapamil ChEBI
(2R)-(+)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile ChEBI
(R)-(+)-verapamil ChEBI
(R)-verapamil ChEBI
Registry Numbers Types Sources
3657914 Reaxys Registry Number Reaxys
38321-02-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
7636539 PubMed citation Europe PMC
8698736 PubMed citation Europe PMC
8698738 PubMed citation Europe PMC
8698739 PubMed citation Europe PMC
8698740 PubMed citation Europe PMC
8712693 PubMed citation Europe PMC
Last Modified
18 March 2014