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Q3625

Quinidine

Name: Quinidine
Brand: SIGMA

sodium channel blocker

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₄N₂O₂

CAS Number:

56-54-2

Molecular Weight:

324.42

NACRES:

NA.77

PubChem Substance ID:

24899331

UNSPSC Code:

12352200

EC Number:

200-279-0

MDL number:

MFCD00135581

Beilstein/REAXYS Number:

91866

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Properties

Product Name

Quinidine, anhydrous

grade

anhydrous

Quality Segment

200

impurities

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

mp

168-172 °C (lit.)

originator

Bayer

SMILES string

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

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

InChI key

LOUPRKONTZGTKE-LHHVKLHASA-N

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)

Description

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

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).

Class IA antiarrhythmic; potassium channel blocker.

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.