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CHEBI:77734 - dexverapamil

ChEBI IDCHEBI:77734
ChEBI Namedexverapamil
Stars
DefinitionA 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.
Last Modified18 March 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC27H38N2O4
Net Charge0
Average Mass454.611
Monoisotopic Mass454.28316
SMILESCOc1ccc(CCN(C)CCC[C@](C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC
InChIInChI=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
InChIKeySGTNSNPWRIOYBX-HHHXNRCGSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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).
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
dexverapamilWHO MedNet
dexvérapamilWHO MedNet
dexverapamiloWHO MedNet
dexverapamilumWHO MedNet
Synonyms  Source
(+)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrileChEBI
(+)-(2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrileChEBI
(2R)-(+)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrileChEBI
(+)-3-(3,4-dimethoxyphenyl)-6-((5,6-dimethoxyphenethyl)methylamino)hexane-3-carbonitrileChEBI
(+)-(R)-5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrileChemIDplus
(+)-(R)-verapamilChEBI
Registry NumbersSources
Reaxys:3657914Reaxys
CAS:38321-02-7ChemIDplus
Citations