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Merck

Q3625

Quinidine

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

Product Name

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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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

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301,H317

Hazard Classifications

Acute Tox. 3 Oral - Skin Sens. 1

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7633
BCCK5236
BCCH3397
BCCF9916
BCCC9051

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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
Effects of quinidine and verapamil on human cardiovascular alpha1-adrenoceptors
Shibata K, et al.
Circulation, 97(13), 1227-1230 (1998)
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)
Cardiac Sodium Channel Disorders An Issue of Cardiac Electrophysiology Clinics E-Book, 6(4) (2015)
Pharmacological evaluation of C-3 modified Betulinic acid derivatives with potent anticancer activity
Rajendran P, et al.
Investigational New Drugs, 26(1), 25-34 (2008)
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