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Details

Stereochemistry RACEMIC
Molecular Formula C26H36N2O4
Molecular Weight 440.576
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORVERAPAMIL

SMILES

CC(C)C(CCCNCCc1ccc(c(c1)OC)OC)(C#N)c2ccc(c(c2)OC)OC

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

Molecular Formula C26H36N2O4
Molecular Weight 440.576
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Approval Year

PubMed

PubMed

TitleDatePubMed
Effect of intraovarian factors on porcine follicular cells: cumulus expansion, granulosa and cumulus cell progesterone production.
2001 Jan 31
A validated method for the determination of verapamil and norverapamil in human plasma.
2001 Jun
Effects of grapefruit juice and smoking on verapamil concentrations in steady state.
2002 Apr
Demonstration of direct bioanalysis of drugs in plasma using nanoelectrospray infusion from a silicon chip coupled with tandem mass spectrometry.
2003 Feb 15
Verapamil: metabolism in cultures of primary human coronary arterial endothelial cells.
2003 Jul
Enantioselective transport and CYP3A4-mediated metabolism of R/S-verapamil in Caco-2 cell monolayers.
2003 May
St John's wort decreases the bioavailability of R- and S-verapamil through induction of the first-pass metabolism.
2004 Apr
The effect of quercetin on the pharmacokinetics of verapamil and its major metabolite, norverapamil, in rabbits.
2004 Dec
Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites.
2004 Feb
Cytochrome P450 3A4 and P-glycoprotein expression in human small intestinal enterocytes and hepatocytes: a comparative analysis in paired tissue specimens.
2004 Mar
Simultaneous quantification of the enantiomers of verapamil and its N-demethylated metabolite in human plasma using liquid chromatography-tandem mass spectrometry.
2004 May 25
Influence of rifampicin on the expression and function of human intestinal cytochrome P450 enzymes.
2005 Feb
Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil.
2005 May
Effects of naringin on the pharmacokinetics of verapamil and one of its metabolites, norverapamil, in rabbits.
2005 Oct
Development of an in vitro rat intestine segmental perfusion model to investigate permeability and predict oral fraction absorbed.
2006 Jul
Chiral capillary electrophoretic analysis of verapamil metabolism by cytochrome P450 3A4.
2006 Jul 7
The effect of gender on the pharmacokinetics of verapamil and norverapamil in human.
2006 Oct
Managing hypertension in diabetic patients--focus on trandolapril/verapamil combination.
2007
Simultaneous analysis of the enantiomers of verapamil and norverapamil in rat plasma by liquid chromatography-tandem mass spectrometry.
2007 Dec 21
Simultaneous determination of ten antiarrhythic drugs and a metabolite in human plasma by liquid chromatography--tandem mass spectrometry.
2007 Mar 1
Computational approaches that predict metabolic intermediate complex formation with CYP3A4 (+b5).
2007 Sep
Enhanced bioavailability of verapamil after oral administration with hesperidin in rats.
2008 Apr
Effects of angiotensin II blockade on inflammation-induced alterations of pharmacokinetics and pharmacodynamics of calcium channel blockers.
2008 Jan
Stereoselective first-pass metabolism of verapamil in the small intestine and liver in rats.
2008 Oct
Effect of pioglitazone on the pharmacokinetics of verapamil and its major metabolite, norverapamil, in rats.
2008 Sep
Effects of simvastatin on the pharmacokinetics of verapamil and its main metabolite, norverapamil, in rats.
2009 Jul-Sep
Different effects of ketoconazole on the stereoselective first-pass metabolism of R/S-verapamil in the intestine and the liver: important for the mechanistic understanding of first-pass drug-drug interactions.
2009 Nov
Effect of Huang-Lian-Jie-Du-Decoction on pharmacokinetics of verapamil in rats.
2010 Apr
Metabolic activity and mRNA levels of human cardiac CYP450s involved in drug metabolism.
2010 Dec 14
Pharmacokinetic interaction between oral lovastatin and verapamil in healthy subjects: role of P-glycoprotein inhibition by lovastatin.
2010 Mar
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:16:04 UTC 2021
Edited
by admin
on Sat Jun 26 02:16:04 UTC 2021
Record UNII
957Z3K3R56
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORVERAPAMIL
WHO-DD  
Common Name English
N-NORVERAPAMIL
Common Name English
(+/-)-NORVERAPAMIL
Common Name English
VERAPAMIL HYDROCHLORIDE IMPURITY J [EP]
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
NORVERAPAMIL [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
957Z3K3R56
Created by admin on Sat Jun 26 02:16:04 UTC 2021 , Edited by admin on Sat Jun 26 02:16:04 UTC 2021
PRIMARY
WIKIPEDIA
Norverapamil
Created by admin on Sat Jun 26 02:16:04 UTC 2021 , Edited by admin on Sat Jun 26 02:16:04 UTC 2021
PRIMARY
EVMPD
SUB33734
Created by admin on Sat Jun 26 02:16:04 UTC 2021 , Edited by admin on Sat Jun 26 02:16:04 UTC 2021
PRIMARY
PUBCHEM
104972
Created by admin on Sat Jun 26 02:16:04 UTC 2021 , Edited by admin on Sat Jun 26 02:16:04 UTC 2021
PRIMARY
CAS
67018-85-3
Created by admin on Sat Jun 26 02:16:04 UTC 2021 , Edited by admin on Sat Jun 26 02:16:04 UTC 2021
PRIMARY
ECHA (EC/EINECS)
266-544-8
Created by admin on Sat Jun 26 02:16:04 UTC 2021 , Edited by admin on Sat Jun 26 02:16:04 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
BINDER->LIGAND
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY