NORVERAPAMIL

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H36N2O4
Molecular Weight	440.575
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(CCNCCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1OC

InChI

InChIKey=UPKQNCPKPOLASS-UHFFFAOYSA-N

InChI=1S/C26H36N2O4/c1-19(2)26(18-27,21-9-11-23(30-4)25(17-21)32-6)13-7-14-28-15-12-20-8-10-22(29-3)24(16-20)31-5/h8-11,16-17,19,28H,7,12-15H2,1-6H3

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Effect of intraovarian factors on porcine follicular cells: cumulus expansion, granulosa and cumulus cell progesterone production.	2001 Jan 31	11182513
Chiral separation of verapamil and some of its metabolites by HPLC and CE.	2001 Jul	11487971
A validated method for the determination of verapamil and norverapamil in human plasma.	2001 Jun	11377051
Pharmacokinetics of verapamil and norverapamil from controlled release floating pellets in humans.	2002 Jan	11777750
Verapamil: metabolism in cultures of primary human coronary arterial endothelial cells.	2003 Jul	12814965
Enantioselective transport and CYP3A4-mediated metabolism of R/S-verapamil in Caco-2 cell monolayers.	2003 May	12729862
HPLC/MS findings in a fatality involving sustained-release verapamil.	2003 Sep	14580012
Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites.	2004 Feb	14744949
Simultaneous quantification of the enantiomers of verapamil and its N-demethylated metabolite in human plasma using liquid chromatography-tandem mass spectrometry.	2004 May 25	15081924
Cytochrome P450 enzyme-mediated drug metabolism at exposure to acute hypoxia (corresponding to an altitude of 4,500 m).	2005 Mar	15692829
Sensitive determination of clarithromycin in human plasma by high-performance liquid chromatography with spectrophotometric detection.	2005 Mar 25	15686985
Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil.	2005 May	15689501
Effects of naringin on the pharmacokinetics of verapamil and one of its metabolites, norverapamil, in rabbits.	2005 Oct	16013069
Effect of naringin pretreatment on bioavailability of verapamil in rabbits.	2006 Jan	16491851
Development of an in vitro rat intestine segmental perfusion model to investigate permeability and predict oral fraction absorbed.	2006 Jul	16779709
Chiral capillary electrophoretic analysis of verapamil metabolism by cytochrome P450 3A4.	2006 Jul 7	16376901
The effect of short- and long-term administration of verapamil on the disposition of cytochrome P450 3A and P-glycoprotein substrates.	2006 Mar	16513446
Managing hypertension in diabetic patients--focus on trandolapril/verapamil combination.	2007	17969376
Simultaneous determination of ten antiarrhythic drugs and a metabolite in human plasma by liquid chromatography--tandem mass spectrometry.	2007 Mar 1	17113839
Comparison of sub-2-microm particle columns for fast metabolite ID.	2007 May	17595954
Enhanced bioavailability of verapamil after oral administration with hesperidin in rats.	2008 Apr	18449511
Drug-drug interaction studies in preclinical species: should metabolite(s) kinetics be studied?	2009 Mar	19280517
Effects of oral epigallocatechin gallate on the oral pharmacokinetics of verapamil in rats.	2009 Mar	19226653
Clinically important interaction between tedisamil and verapamil.	2009 May	19299533
Intravenous fat emulsion therapy for intentional sustained-release verapamil overdose.	2009 May	19282085
Effect of Huang-Lian-Jie-Du-Decoction on pharmacokinetics of verapamil in rats.	2010 Apr	20604832

Name

Type

Language

NORVERAPAMIL

Common Name

English

VERAPAMIL HYDROCHLORIDE IMPURITY J [EP IMPURITY]

Common Name

English

N-NORVERAPAMIL

Common Name

English

(±)-NORVERAPAMIL

Common Name

English

Norverapamil [WHO-DD]

Common Name

English

D-591

Code

English

BENZENEACETONITRILE, .ALPHA.-(3-((2-(3,4-DIMETHOXYPHENYL)ETHYL)AMINO)PROPYL)-3,4-DIMETHOXY-.ALPHA.-(1-METHYLETHYL)-

Systematic Name

English

(2RS)-2-(3,4-DIMETHOXYPHENYL)-5-((2-(3,4-DIMETHOXY-PHENYL)ETHYL)AMINO)-2-(1-METHYLETHYL)PENTANENITRILE

Systematic Name

English

Code System Code Type Description

FDA UNII

957Z3K3R56