CHEBI:77739 - dexverapamil hydrochloride

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ChEBI Name dexverapamil hydrochloride
ChEBI ID CHEBI:77739
Definition A hydrochloride salt resulting from the reaction of equimolar amounts of dexverapamil and hydrogen chloride. 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 hydrochloride exhibits lower calcium antagonistic activity and toxicity than racemic verapamil hydrochloride.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H39ClN2O4
Net Charge 0
Average Mass 491.06300
Monoisotopic Mass 490.25984
InChI InChI=1S/C27H38N2O4.ClH/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;1H/t27-;/m1./s1
InChIKey DOQPXTMNIUCOSY-HZPIKELBSA-N
SMILES Cl.COc1ccc(CCN(C)CCC[C@@](C#N)(C(C)C)c2ccc(OC)c(OC)c2)cc1OC
Roles Classification
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).
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ChEBI Ontology
Outgoing dexverapamil hydrochloride (CHEBI:77739) has part dexverapamil(1+) (CHEBI:77737)
dexverapamil hydrochloride (CHEBI:77739) has role EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor (CHEBI:77748)
dexverapamil hydrochloride (CHEBI:77739) is a hydrochloride (CHEBI:36807)
dexverapamil hydrochloride (CHEBI:77739) is enantiomer of (S)-verapamil hydrochloride (CHEBI:77741)
Incoming verapamil hydrochloride (CHEBI:53188) has part dexverapamil hydrochloride (CHEBI:77739)
(S)-verapamil hydrochloride (CHEBI:77741) is enantiomer of dexverapamil hydrochloride (CHEBI:77739)
IUPAC Names
(2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentanenitrile hydrochloride
(4R)-4-cyano-4-(3,4-dimethoxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N,5-dimethylhexan-1-aminium chloride
Synonyms Sources
dexverapamil HCl ChEBI
dexverapamil.HCl ChEBI
Registry Number Type Source
6710895 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21544450 PubMed citation Europe PMC
Last Modified
18 March 2014