Q3625

Quinidine

Name: Quinidine
Brand: SIGMA

sodium channel blocker

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About This Item

Formule empirique (notation de Hill) :

C₂₀H₂₄N₂O₂

Numéro CAS:

56-54-2

Poids moléculaire :

324.42

NACRES:

NA.77

PubChem Substance ID:

24899331

UNSPSC Code:

12352200

EC Number:

200-279-0

MDL number:

MFCD00135581

Beilstein/REAXYS Number:

91866

Nom du produit

Quinidine, anhydrous

InChI key

LOUPRKONTZGTKE-LHHVKLHASA-N

InChI

1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-/m0/s1

SMILES string

COc1ccc2nccc([C@H](O)C3CC4CCN3C[C@@H]4C=C)c2c1

grade

anhydrous

impurities

≤20% Dihydroquinidine (according to USP specifications., actual content given on label)

mp

168-172 °C (lit.)

originator

Bayer

Quality Level

200

Gene Information

human ... ABCB1(5243), CYP2D6(1565), CYP3A4(1576), KCNH1(3756), SCN10A(6336), SCN11A(11280), SCN1A(6323), SCN2A(6326), SCN3A(6328), SCN4A(6329), SCN5A(6331), SCN7A(6332), SCN8A(6334), SCN9A(6335)
mouse ... Abcb1a(18671), Abcb1b(18669)
rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522)

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Catégories apparentées

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Quinidine has been used:

as an inhibitor of cytochrome P450 enzyme isoform CYP2D6
as a potassium (K⁺) channel blocker in microglia
to test its effect on electrophysiological behaviour of human induced pluripotent stem cells (hiPSC) cardiomyocytes

Biochem/physiol Actions

Class IA antiarrhythmic; potassium channel blocker.

Quinidine, an isomer of quinine has potential side effects like proarrhythmia on usage. It prolongs cardiac potential and is sodium channel blocker. It is a potential antagonist for α1-adrenoceptors and contributes to hypotension. It inhibits cytochrome P450 2D6 and improves circulation and brain penetration of dementia drug, dextromethorphan. Quinidine-dextromethorphan combination may be useful in treating pseudobulbar affect (PBA).

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

GHS06

signalword

Danger

hcodes

H301,H317

pcodes

P261 - P264 - P272 - P280 - P301 + P310 - P302 + P352

Hazard Classifications

Acute Tox. 3 Oral - Skin Sens. 1

Classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Consulter la Bibliothèque de documents

Action potential-based MEA platform for in vitro screening of drug-induced cardiotoxicity using human iPSCs and rat neonatal myocytes.

Danny Jans et al.

Journal of pharmacological and toxicological methods, 87, 48-52 (2017-05-28)

Drug-induced cardiotoxicity poses a negative impact on public health and drug development. Cardiac safety pharmacology issues urged for the preclinical assessment of drug-induced ventricular arrhythmia leading to the design of several in vitro electrophysiological screening assays. In general, patch clamp

Microglial ramification, surveillance, and interleukin-1beta release are regulated by the two-pore domain K+ channel THIK-1

Madry C, et al.

Neuron, 97(2), 299-312 (2018)

Effects of quinidine and verapamil on human cardiovascular alpha1-adrenoceptors

Shibata K, et al.

Circulation, 97(13), 1227-1230 (1998)

Cardiac Sodium Channel Disorders An Issue of Cardiac Electrophysiology Clinics E-Book, 6(4) (2015)

Dextromethorphan/quinidine: a review of its use in adults with pseudobulbar affect

Yang LPH and Deeks ED

Drugs, 75(1), 83-90 (2015)

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