CAS 67812-42-4|Norverapamil hydrochloride

Introduction：Basic information about CAS 67812-42-4|Norverapamil hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Norverapamil hydrochloride BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles30
6. Synonyms

Common Name	Norverapamil hydrochloride
CAS Number	67812-42-4	Molecular Weight	477.04
Density	/	Boiling Point	/
Molecular Formula	C₂₆H₃₇ClN₂O₄	Melting Point	155-160â„ƒ dec.
MSDS	ChineseUSA	Flash Point	/
Symbol	GHS07	Signal Word	Warning

Names

Name	2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethylamino]-2-propan-2-ylpentanenitrile,hydrochloride
Synonym	More Synonyms

Norverapamil hydrochloride BiologicalActivity

Description	Norverapamil is a calcium channel blocker， it is the main active metabolite of verapamil.In vitro: Norverapamil is similarly effective as verapamil at inhibiting isoniazid and rifampicin tolerance and killing of intracellular M. tuberculosis in the absence of other drugs. norverapamil, also inhibits macrophage-induced tolerance and achieves similar serum levels to verapamil.[1] Norverapamil (NOR) is the major metabolite and shows approximately 20% of the efficacy of VER with regard to the vasodilation effect, but shows no antiarrhythmic activity. [2] Verapamil and its major metabolite norverapamil were identified to be both mechanism-based inhibitors and substrates of CYP3A and reported to have non-linear pharmacokinetics in clinic. [3]
Related Catalog	Signaling Pathways >>Membrane Transporter/Ion Channel >>Calcium ChannelResearch Areas >>Cardiovascular Disease
References	[1]. Adams KN et al. Verapamil, and its metabolite norverapamil, inhibit macrophage-induced, bacterial efflux pump-mediated tolerance to multiple anti-tubercular drugs. J Infect Dis. 2014 Aug 1;210(3):456-66. [2]. Singhal P et al. Enantiomeric separation of verapamil and its active metabolite, norverapamil, and simultaneous quantification in human plasma by LC-ESI-MS-MS. J Chromatogr Sci. 2012 Oct;50(9):839-48. [3]. Wang J et al. A semi-physiologically-based pharmacokinetic model characterizing mechanism-based auto-inhibition to predict stereoselective pharmacokinetics of verapamil and its metabolite norverapamil in human. Eur J Pharm Sci. 2013 Nov 20;50(3-4):290-302.

Description

Norverapamil is a calcium channel blocker， it is the main active metabolite of verapamil.In vitro: Norverapamil is similarly effective as verapamil at inhibiting isoniazid and rifampicin tolerance and killing of intracellular M. tuberculosis in the absence of other drugs. norverapamil, also inhibits macrophage-induced tolerance and achieves similar serum levels to verapamil.[1] Norverapamil (NOR) is the major metabolite and shows approximately 20% of the efficacy of VER with regard to the vasodilation effect, but shows no antiarrhythmic activity. [2] Verapamil and its major metabolite norverapamil were identified to be both mechanism-based inhibitors and substrates of CYP3A and reported to have non-linear pharmacokinetics in clinic. [3]

Related Catalog

Signaling Pathways >>Membrane Transporter/Ion Channel >>Calcium ChannelResearch Areas >>Cardiovascular Disease

References

[1]. Adams KN et al. Verapamil, and its metabolite norverapamil, inhibit macrophage-induced, bacterial efflux pump-mediated tolerance to multiple anti-tubercular drugs. J Infect Dis. 2014 Aug 1;210(3):456-66.

[2]. Singhal P et al. Enantiomeric separation of verapamil and its active metabolite, norverapamil, and simultaneous quantification in human plasma by LC-ESI-MS-MS. J Chromatogr Sci. 2012 Oct;50(9):839-48.

[3]. Wang J et al. A semi-physiologically-based pharmacokinetic model characterizing mechanism-based auto-inhibition to predict stereoselective pharmacokinetics of verapamil and its metabolite norverapamil in human. Eur J Pharm Sci. 2013 Nov 20;50(3-4):290-302.

Chemical & Physical Properties

Melting Point	155-160â„ƒ dec.
Molecular Formula	C₂₆H₃₇ClN₂O₄
Molecular Weight	477.04
LogP	2.02400
InChIKey	OEAFTRIDBHSJDC-UHFFFAOYSA-N
SMILES	COc1ccc(CCNCCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC.Cl
Storage condition	2-8℃

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302-H315-H319-H335
Precautionary Statements	P301 + P312 + P330-P305 + P351 + P338
Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	UN 2811 6.1/PG 3

Articles30

Verapamil, and its metabolite norverapamil, inhibit macrophage-induced, bacterial efflux pump-mediated tolerance to multiple anti-tubercular drugs.

J. Infect. Dis. 210(3) , 456-66, (2014)

Drug tolerance likely represents an important barrier to tuberculosis treatment shortening. We previously implicated the Mycobacterium tuberculosis efflux pump Rv1258c as mediating macrophage-induced ...

Application of permeability-limited physiologically-based pharmacokinetic models: part II - prediction of P-glycoprotein mediated drug-drug interactions with digoxin.

J. Pharm. Sci. 102(9) , 3161-73, (2013)

Digoxin is the recommended substrate for assessment of P-glycoprotein (P-gp)-mediated drug-drug interactions (DDIs) in vivo. The overall aim of our study was to investigate the inhibitory potential of...

Stereoselective CZE method for analysis of verapamil and norverapamil in human plasma.

Acta Pol. Pharm. 70(3) , 395-401, (2013)

A stereospecific capillary zone electrophoresis (CZE) method was developed for the determination of verapamil (VER) and its main metabolite norverapamil (NOR) in human plasma. Optimal temperature, cyc...

Synonyms

N-Nor-(+/-)-verapamil hydrochloride

Nor Verapamil Hydrochloride

Norverapamil hydrochloride

Norverapamil (hydrochloride)

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