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

Molecular Formula	C26H36N2O4
Molecular Weight	440.575
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

PubMed

Title	Date	PubMed
The impact of P-glycoprotein efflux on enterocyte residence time and enterocyte-based metabolism of verapamil.	2001 Dec	11804391
Effects of grapefruit juice and smoking on verapamil concentrations in steady state.	2002 Apr	11956673
Pharmacokinetics of verapamil and norverapamil from controlled release floating pellets in humans.	2002 Jan	11777750
Pharmacokinetics of verapamil and its metabolite norverapamil from a buccal drug formulation.	2002 May 15	11996822
Demonstration of direct bioanalysis of drugs in plasma using nanoelectrospray infusion from a silicon chip coupled with tandem mass spectrometry.	2003 Feb 15	12622370
Enantioselective transport and CYP3A4-mediated metabolism of R/S-verapamil in Caco-2 cell monolayers.	2003 May	12729862
Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites.	2004 Feb	14744949
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
Effect of naringin pretreatment on bioavailability of verapamil in rabbits.	2006 Jan	16491851
Managing hypertension in diabetic patients--focus on trandolapril/verapamil combination.	2007	17969376
Enhanced bioavailability of verapamil after oral administration with hesperidin in rats.	2008 Apr	18449511
Dietary salt does not influence the disposition of verapamil enantiomers in relation to efflux transporter ABCB1 genetic polymorphism in healthy Korean subjects.	2008 Apr	18340565
Reduction of enantioselectivity in the kinetic disposition and metabolism of verapamil in rats exposed to toluene.	2008 May	18432283
Drug interaction between oral atorvastatin and verapamil in healthy subjects: effects of atorvastatin on the pharmacokinetics of verapamil and norverapamil.	2008 May	18193210
Stereoselective first-pass metabolism of verapamil in the small intestine and liver in rats.	2008 Oct	18617604
Effect of pioglitazone on the pharmacokinetics of verapamil and its major metabolite, norverapamil, in rats.	2008 Sep	18806964
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
Effects of lovastatin on the pharmacokinetics of verapamil and its active metabolite, norverapamil in rats: possible role of P-glycoprotein inhibition by lovastatin.	2009 Oct	19898809
Metabolic activity and mRNA levels of human cardiac CYP450s involved in drug metabolism.	2010 Dec 14	21179487

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:21:33 UTC 2023` Edited by `admin` on `Sat Dec 16 10:21:33 UTC 2023`
Record UNII	957Z3K3R56
Record Status	`Validated (UNII)`
Record Version

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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