QUINIDINE HYDROCHLORIDE

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24N2O2.ClH
Molecular Weight	360.878
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@@H](O)C3=C4C=C(OC)C=CC4=NC=C3

InChI

InChIKey=LBSFSRMTJJPTCW-VJAUXQICSA-N

InChI=1S/C20H24N2O2.ClH/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;1H/t13-,14-,19+,20-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C20H24N2O2
Molecular Weight	324.4168
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/pro/quinidine.html
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17506538 | https://www.ncbi.nlm.nih.gov/pubmed/22761000 | https://www.ncbi.nlm.nih.gov/pubmed/22512909 | https://www.ncbi.nlm.nih.gov/pubmed/21832259

Quinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent (Ia) in the heart. It is a stereoisomer of quinine, originally derived from the bark of the cinchona tree. The drug causes increased action potential duration, as well as a prolonged QT interval. Like all other class I antiarrhythmic agents, quinidine primarily works by blocking the fast inward sodium current (INa). Quinidine's effect on INa is known as a 'use-dependent block'. This means at higher heart rates, the block increases, while at lower heart rates, the block decreases. The effect of blocking the fast inward sodium current causes the phase 0 depolarization of the cardiac action potential to decrease (decreased Vmax). Quinidine also blocks the slowly inactivating, tetrodotoxin-sensitive Na current, the slow inward calcium current (ICA), the rapid (IKr) and slow (IKs) components of the delayed potassium rectifier current, the inward potassium rectifier current (IKI), the ATP-sensitive potassium channel (IKATP) and Ito. Quinidine is also an inhibitor of the cytochrome P450 enzyme 2D6 and can lead to increased blood levels of lidocaine, beta blockers, opioids, and some antidepressants. Quinidine also inhibits the transport protein P-glycoprotein and so can cause some peripherally acting drugs such as loperamide to have central nervous system side effects, such as respiratory depression if the two drugs are coadministered. Quinidine can cause thrombocytopenia, granulomatous hepatitis, myasthenia gravis, and torsades de pointes, so is not used much today. Torsades can occur after the first dose. Quinidine-induced thrombocytopenia (low platelet count) is mediated by the immune system and may lead to thrombocytic purpura. A combination of dextromethorphan and quinidine has been shown to alleviate symptoms of easy laughing and crying (pseudobulbar affect) in patients with amyotrophic lateral sclerosis and multiple sclerosis. This drug is marketed as Nuedexta in the United States. Intravenous quinidine is also indicated for the treatment of Plasmodium falciparum malaria. However, quinidine is not considered the first-line therapy for P. falciparum. The recommended treatments for P. falciparum malaria, according to the Toronto Notes 2008, are a combination of either quinine and doxycycline or atovaquone and proguanil (Malarone). The drug is also effective for the treatment of atrial fibrillation in horses.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Voltage-gated potassium channel subunit Kv1.5 37 Target ID: CHEMBL4306 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17506538	Inhibitor 8297	7300.0 nM [IC50]
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17506538	Inhibitor 8297	6900.0 nM [IC50]
Potassium voltage-gated channel subfamily D member 2 15 Target ID: CHEMBL5885 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17506538	Inhibitor 8297	2200.0 nM [IC50]
Voltage-gated L-type calcium channel alpha-1C subunit 44 Target ID: CHEMBL1940 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22761000	Inhibitor 8297	19820.0 nM [IC50]
Potassium voltage-gated channel subfamily B member 1 17 Target ID: CHEMBL1075226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17506538	Inhibitor 8297
Plasmodium falciparum 74 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22512909	Inhibitor 8297	18.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Plasmodium falciparum malaria 63 Sources: https://www.drugs.com/pro/quinidine.html	Primary	Approved 8429	QUINIDINE GLUCONATE Approved Use Conversion of atrial fibrillation/flutter In patients with symptomatic atrial fibrillation/flutter whose symptoms are not adequately controlled by measures that reduce the rate of ventricular response, quinidine sulfate is indicated as a means of restoring normal sinus rhythm. If this use of quinidine sulfate does not restore sinus rhythm within a reasonable time (see ), then quinidine sulfate should be discontinued. DOSAGE AND ADMINISTRATION Reduction of frequency of relapse into atrial fibrillation/flutter Chronic therapy with quinidine sulfate is indicated for some patients at high risk of symptomatic atrial fibrillation/flutter, generally patients who have had previous episodes of atrial fibrillation/flutter that were so frequent and poorly tolerated as to outweigh, in the judgment of the physician and the patient, the risks of prophylactic therapy with quinidine sulfate. The increased risk of death should specifically be considered. Quinidine sulfate should be used only after alternative measures ( use of other drugs to control the ventricular rate) have been found to be inadequate. e.g., In patients with histories of frequent symptomatic episodes of atrial fibrillation/flutter, the goal of therapy should be an increase in the average time between episodes. In most patients, the tachyarrhythmia during therapy, and a single recurrence should not be interpreted as therapeutic failure. will recur Suppression of ventricular arrhythmias Quinidine sulfate is also indicated for the suppression of recurrent documented ventricular arrhythmias, such as sustained ventricular tachycardia, that in the judgment of the physician are life-threatening. Because of the proarrhythmic effects of quinidine, its use with ventricular arrhythmias of lesser severity is generally not recommended, and treatment of patients with asymptomatic ventricular premature contractions should be avoided. Where possible, therapy should be guided by the results of programmed electrical stimulation and/or Holter monitoring with exercise. Antiarrhythmic drugs (including quinidine sulfate) have not been shown to enhance survival in patients with ventricular arrhythmias. Treatment of malaria Quinidine sulfate is also indicated in the treatment of life-threatening malaria. Plasmodium falciparum Launch Date 1950
Atrial fibrillation 131 Sources: https://www.drugs.com/pro/quinidine.html	Primary	Approved 8429	QUINIDINE GLUCONATE Approved Use Conversion of atrial fibrillation/flutter In patients with symptomatic atrial fibrillation/flutter whose symptoms are not adequately controlled by measures that reduce the rate of ventricular response, quinidine sulfate is indicated as a means of restoring normal sinus rhythm. If this use of quinidine sulfate does not restore sinus rhythm within a reasonable time (see ), then quinidine sulfate should be discontinued. DOSAGE AND ADMINISTRATION Reduction of frequency of relapse into atrial fibrillation/flutter Chronic therapy with quinidine sulfate is indicated for some patients at high risk of symptomatic atrial fibrillation/flutter, generally patients who have had previous episodes of atrial fibrillation/flutter that were so frequent and poorly tolerated as to outweigh, in the judgment of the physician and the patient, the risks of prophylactic therapy with quinidine sulfate. The increased risk of death should specifically be considered. Quinidine sulfate should be used only after alternative measures ( use of other drugs to control the ventricular rate) have been found to be inadequate. e.g., In patients with histories of frequent symptomatic episodes of atrial fibrillation/flutter, the goal of therapy should be an increase in the average time between episodes. In most patients, the tachyarrhythmia during therapy, and a single recurrence should not be interpreted as therapeutic failure. will recur Suppression of ventricular arrhythmias Quinidine sulfate is also indicated for the suppression of recurrent documented ventricular arrhythmias, such as sustained ventricular tachycardia, that in the judgment of the physician are life-threatening. Because of the proarrhythmic effects of quinidine, its use with ventricular arrhythmias of lesser severity is generally not recommended, and treatment of patients with asymptomatic ventricular premature contractions should be avoided. Where possible, therapy should be guided by the results of programmed electrical stimulation and/or Holter monitoring with exercise. Antiarrhythmic drugs (including quinidine sulfate) have not been shown to enhance survival in patients with ventricular arrhythmias. Treatment of malaria Quinidine sulfate is also indicated in the treatment of life-threatening malaria. Plasmodium falciparum Launch Date 1950
Ventricular arrhythmia 50 Sources: https://www.drugs.com/pro/quinidine.html	Primary	Approved 8429	QUINIDINE GLUCONATE Approved Use Conversion of atrial fibrillation/flutter In patients with symptomatic atrial fibrillation/flutter whose symptoms are not adequately controlled by measures that reduce the rate of ventricular response, quinidine sulfate is indicated as a means of restoring normal sinus rhythm. If this use of quinidine sulfate does not restore sinus rhythm within a reasonable time (see ), then quinidine sulfate should be discontinued. DOSAGE AND ADMINISTRATION Reduction of frequency of relapse into atrial fibrillation/flutter Chronic therapy with quinidine sulfate is indicated for some patients at high risk of symptomatic atrial fibrillation/flutter, generally patients who have had previous episodes of atrial fibrillation/flutter that were so frequent and poorly tolerated as to outweigh, in the judgment of the physician and the patient, the risks of prophylactic therapy with quinidine sulfate. The increased risk of death should specifically be considered. Quinidine sulfate should be used only after alternative measures ( use of other drugs to control the ventricular rate) have been found to be inadequate. e.g., In patients with histories of frequent symptomatic episodes of atrial fibrillation/flutter, the goal of therapy should be an increase in the average time between episodes. In most patients, the tachyarrhythmia during therapy, and a single recurrence should not be interpreted as therapeutic failure. will recur Suppression of ventricular arrhythmias Quinidine sulfate is also indicated for the suppression of recurrent documented ventricular arrhythmias, such as sustained ventricular tachycardia, that in the judgment of the physician are life-threatening. Because of the proarrhythmic effects of quinidine, its use with ventricular arrhythmias of lesser severity is generally not recommended, and treatment of patients with asymptomatic ventricular premature contractions should be avoided. Where possible, therapy should be guided by the results of programmed electrical stimulation and/or Holter monitoring with exercise. Antiarrhythmic drugs (including quinidine sulfate) have not been shown to enhance survival in patients with ventricular arrhythmias. Treatment of malaria Quinidine sulfate is also indicated in the treatment of life-threatening malaria. Plasmodium falciparum Launch Date 1950

C_max

Value	Dose	Co-administered	Analyte	Population
3.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/512840/	3.74 mg/kg single, oral dose: 3.74 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		QUINIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
12.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/512840/	3.74 mg/kg single, oral dose: 3.74 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		QUINIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/512840/	3.74 mg/kg single, oral dose: 3.74 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		QUINIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/089338s036lbl.pdf	202 mg single, oral dose: 202 mg route of administration: Oral experiment type: SINGLE co-administered:		QUINIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
12% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/089338s036lbl.pdf	202 mg single, oral dose: 202 mg route of administration: Oral experiment type: SINGLE co-administered:		QUINIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg 4 times / day multiple, oral Dose: 200 mg, 4 times / day Route: oral Route: multiple Dose: 200 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1269875	unhealthy, 47 years n = 1 Health Status: unhealthy Age Group: 47 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1269875	Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity Sources: https://pubmed.ncbi.nlm.nih.gov/1269875
324 mg 5 times / day multiple, oral Dose: 324 mg, 5 times / day Route: oral Route: multiple Dose: 324 mg, 5 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7604299	unhealthy, 56 yeras n = 1 Health Status: unhealthy Age Group: 56 yeras Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7604299	Disc. AE: Myalgia... AEs leading to discontinuation/dose reduction: Myalgia (severe, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7604299
4 g single, oral Overdose Dose: 4 g Route: oral Route: single Dose: 4 g Sources: https://pubmed.ncbi.nlm.nih.gov/5557506	healthy, 57 years n = 1 Health Status: healthy Age Group: 57 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5557506	Other AEs: Grand mal convulsion, Cardiotoxicity... Other AEs: Grand mal convulsion (1 patient) Cardiotoxicity (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/5557506
324 mg 3 times / day multiple, oral Dose: 324 mg, 3 times / day Route: oral Route: multiple Dose: 324 mg, 3 times / day Co-administed with:: digoxin levothyroxine sodium crystalline warfarin sodium Sources: https://pubmed.ncbi.nlm.nih.gov/7604299	unhealthy, 79 years n = 1 Health Status: unhealthy Age Group: 79 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7604299	Disc. AE: Drug-induced lupus erythematosus... AEs leading to discontinuation/dose reduction: Drug-induced lupus erythematosus (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7604299
370 mg 6 times / day multiple, oral Highest studied dose Dose: 370 mg, 6 times / day Route: oral Route: multiple Dose: 370 mg, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6747817	healthy, > 23 years n = 1 Health Status: healthy Age Group: > 23 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6747817	Sources: https://pubmed.ncbi.nlm.nih.gov/6747817
1650 mg single, intravenous Dose: 1650 mg Route: intravenous Route: single Dose: 1650 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6747817	healthy, > 23 years n = 1 Health Status: healthy Age Group: > 23 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6747817	Sources: https://pubmed.ncbi.nlm.nih.gov/6747817

AEs

AE	Significance	Dose	Population
Hepatotoxicity	Disc. AE	200 mg 4 times / day multiple, oral Dose: 200 mg, 4 times / day Route: oral Route: multiple Dose: 200 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1269875	unhealthy, 47 years n = 1 Health Status: unhealthy Age Group: 47 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1269875
Myalgia	severe, 1 patient Disc. AE	324 mg 5 times / day multiple, oral Dose: 324 mg, 5 times / day Route: oral Route: multiple Dose: 324 mg, 5 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7604299	unhealthy, 56 yeras n = 1 Health Status: unhealthy Age Group: 56 yeras Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7604299
Cardiotoxicity	1 patient	4 g single, oral Overdose Dose: 4 g Route: oral Route: single Dose: 4 g Sources: https://pubmed.ncbi.nlm.nih.gov/5557506	healthy, 57 years n = 1 Health Status: healthy Age Group: 57 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5557506
Grand mal convulsion	1 patient	4 g single, oral Overdose Dose: 4 g Route: oral Route: single Dose: 4 g Sources: https://pubmed.ncbi.nlm.nih.gov/5557506	healthy, 57 years n = 1 Health Status: healthy Age Group: 57 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5557506
Drug-induced lupus erythematosus	1 patient Disc. AE	324 mg 3 times / day multiple, oral Dose: 324 mg, 3 times / day Route: oral Route: multiple Dose: 324 mg, 3 times / day Co-administed with:: digoxin levothyroxine sodium crystalline warfarin sodium Sources: https://pubmed.ncbi.nlm.nih.gov/7604299	unhealthy, 79 years n = 1 Health Status: unhealthy Age Group: 79 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7604299

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 inducer 781	substrate 1037 inhibitor 1767	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 OCT1 512 OCT2 647 OCT3 150 MATE1 306 MATE2 263 CYP1A2 1524 CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882	OCTN1 47 OCTN2 50 P-gp 1537 CYP2E1 667	CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021879s000lbl.pdf#page=14 Page: 14.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.tandfonline.com/doi/pdf/10.1080/13880209.2016.1223145#page=5; https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/12796s49lbl.pdf#page=2 Page: 5.0	yes [IC50 0.051 uM]	likely (co-administration study) Comment: Caution must be exercixed whenever quinidine is prescribed together with drugs metabolized by CYP2C6. Sources: https://www.tandfonline.com/doi/pdf/10.1080/13880209.2016.1223145#page=5; https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/12796s49lbl.pdf#page=2 Page: 5.0
OCT3 150	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16141367/	yes [IC50 18.3 uM]
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18971316/	yes [IC50 5.7 uM]
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16141367/	yes [IC50 8.7 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12499648/	yes [IC50 9.52 uM]
MATE2 263	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 23.1 uM]
MATE1 308	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 29.2 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10086984/	minor
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/089338s036lbl.pdf#page=2 Page: 2.0	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10086984/	no
OCTN1 47	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10215651/	yes
OCTN2 50	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10525100/	yes
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10628900/ Page: 4.0	yes
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/089338s036lbl.pdf#page=2 Page: 2.0	yes	likely (co-administration study) Comment: coadministration of quinidine causes variable slowing of the metabolism of nifedipine. Interactions with other dihydropyridine calcium channel blockers have not been reported, but these agents (including felodipine, nicardipine, and nimodipine) are all dependent upon P450IIIA4 for metabolism, so similar interactions with quinidine should be anticipated Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/089338s036lbl.pdf#page=2 Page: 2.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://journals.lww.com/cardiovascularpharm/Fulltext/1999/02000/Modulation_of_HERG_Potassium_Channels_by.2.aspx

Sourcing

Vendor/Aggregator	ID	URL
AEchem Scientific Corp., USA	AE020240	http://www.aechemsc.com/info_products/AE020240.php
AK Scientific, Inc. (AKSCI)	6566AF	http://www.aksci.com/item_detail.php?cat=6566AF
AK Scientific, Inc. (AKSCI)	66338	http://www.aksci.com/item_detail.php?cat=66338
Aaron Chemicals	AR003696	http://www.aaronchem.com/56-54-2
AbMole Bioscience	M3406	http://www.abmole.com/products/quinidine.html
Acadechem	ACDS-067325	http://www.acadechemical.com/product/142024
Achemtek	0104-024048	http://www.achemtek.com/56-54-2
Acorn PharmaTech	ACN-052225	http://www.acornpharmatech.com/
Acros Organics	AC163680250	https://www.fishersci.com/shop/products/quinidine-98-anhydrous-acros-organics-1/AC163680250
Acros Organics	AC163681000	https://www.fishersci.com/shop/products/quinidine-98-anhydrous-acros-organics/AC163681000
Alfa Aesar	A12559	https://www.alfa.com/en/catalog/A12559/
Alfa Chemistry	AP56542-A	https://reagents.alfa-chemistry.com/product/quinidine-cas-56-54-2-13236.html
Alfa Chemistry	AP56542-B	https://reagents.alfa-chemistry.com/product/quinidine-cas-56-54-2-13237.html
Alfa Chemistry	ACM56542	https://www.alfachemic.com/catalysts/product/quinidine-cas-56-54-2-180968.html
Alfa Chemistry	56-54-2	https://www.alfachemic.com/catalysts/quinidine-cas-56-54-2-item-180968.htm
Ambinter	Amb17835341	http://www.ambinter.com/reference/17835341
AstaTech, Inc.	23083	http://www.astatechinc.com/CPSResult.php?CRNO=26833
Aurora Fine Chemicals LLC	A24.073.679	http://online.aurorafinechemicals.com/info?ID=A24.073.679
Aurum Pharmatech LLC	M-7594	http://www.Aurumpharmatech.com/Product/ProductDetails/M_7594
Avantor Inc	BT127895-1G	https://us.vwr.com/store/product/16900231/quinidine
Avantor Inc	BT127895-25G	https://us.vwr.com/store/product/16900231/quinidine
Avantor Inc	BT127895-5G	https://us.vwr.com/store/product/16900231/quinidine
BLD Pharm	BD01139139	http://www.bldpharm.com/products/56-54-2.html
BLD Pharm	BD150056	http://www.bldpharm.com/products/56-54-2.html
BLD Pharm	BD01094112	http://www.bldpharm.com/products/66591-62-6.html
BioCrick	BCC7863	http://www.biocrick.com/Quinidine-BCC7863.html
BioSynth	W-109256	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-109256.html
CSNpharm	CSN11818	https://www.csnpharm.com/products/quinidine.html
Capot Chemical	7994	http://www.capotchem.com/en/7994.htm
Capot Chemical	PubChem7994	http://www.capotchem.com/en/7994.htm
Chem Scene	CS-7812	http://www.chemscene.com/56-54-2.html
ChemMol	1030683	http://www.chemmol.com/chemmol/1030683.html
ChemMol	99106903	http://www.chemmol.com/chemmol/99106903.html
Chemenu	CM108220	http://www.chemenu.com/products/CM108220
Chemspace	CSSB00016988638	https://chem-space.com/CSSB00016988638
DC Chemicals	DC9066	http://www.dcchemicals.com/product_show-Quinidine.html
Glentham Life Sciences	GE1634	http://www.glentham.com/products/product/GE1634/
Huateng Pharma	F94507	https://en.huatengsci.com/products/intermediates/
LGC Standards	LGCFOR1523.01	https://www.lgcstandards.com/US/en/p/LGCFOR1523.01
LGC Standards	MM1523.01	https://www.lgcstandards.com/US/en/p/MM1523.01
Lab Network	LN00173655	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00173655
Lab Network	LN01747538	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01747538
Matrix Scientific	75925	https://www.matrixscientific.com/075925.html
MedChem Express	HY-B1751	https://www.medchemexpress.com/Quinidine.html
MuseChem	R007506	https://www.musechem.com/product/R007506.html
Oakwood	79244	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=64418&ExtHyperLink=1
Parchem	45359	https://www.parchem.com/chemical-supplier-distributor/(1S)-(6-Methoxyquinolin-4-yl)((2R-4S-5R)-5-vinylquinuclidin-2-yl)methanol-045359.aspx
R&D Chemicals	611	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=8191
Sigma-Aldrich	22600_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/22600?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	Q3625_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/q3625?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S752224	https://www.smolecule.com/products/s752224
VladaChem	VL144107	https://www.vladachem.com/product.php?products=56-54-2
VladaChem	VL267661-25G	https://www.vladachem.com/product.php?products=56-54-2
VladaChem	VL270184-25G	https://www.vladachem.com/product.php?products=56-54-2
abcr GmbH	AB121200	http://www.abcr.com/shop/en/AB121200
eNovation Chemicals	D378950	http://www.enovationchem.com/productDetails.asp?productID=D378950
eNovation Chemicals	D593773	https://enovationchem.com/ProductDetails.asp?ProductID=D593773
eNovation Chemicals	D674705	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674705
eNovation Chemicals	D766047	https://www.enovationchem.com/ProductDetails.asp?ProductID=D766047
iChemical	EBD2202687	http://www.ichemical.com/products/56-54-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-7178915526	https://mcule.com/MCULE-7178915526/

PubMed

Title	Date	PubMed
Quinidine-induced lupus nephritis.	1976 May 3	1082944
[Congenital myasthenic syndrome (CMS) caused by postsynaptic defects].	2001	11596412
Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis.	2001	11570976
Alteration of drug kinetics in rats following exposure to trichloroethylene.	2001	11490201
Pharmacokinetic interactions of antimalarial agents.	2001	11432537
Importance of QT interval determination and renal function assessment during antiarrhythmic drug therapy.	2001 Apr	11509917
Influence of phenylalanine-481 substitutions on the catalytic activity of cytochrome P450 2D6.	2001 Apr 15	11284724
[Pharmacokinetics and drug interactions of antidepressive agents].	2001 Aug	11519155
Independent organic cation transport activity of Na(+)-L-carnitine cotransport system in LLC-PK(1) cells.	2001 Aug	11457718
A functional assay for quantitation of the apparent affinities of ligands of P-glycoprotein in Caco-2 cells.	2001 Feb	11405287
Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells.	2001 Feb	11160630
Species plays an important role in drug-induced prolongation of action potential duration and early afterdepolarizations in isolated Purkinje fibers.	2001 Jan	11204092
A method for the simultaneous evaluation of the activities of seven major human drug-metabolizing cytochrome P450s using an in vitro cocktail of probe substrates and fast gradient liquid chromatography tandem mass spectrometry.	2001 Jan	11124225
Evaluation of a vincristine resistant Caco-2 cell line for use in a calcein AM extrusion screening assay for P-glycoprotein interaction.	2001 Jan	11113639
Effect of mdr1a P-glycoprotein gene disruption, gender, and substrate concentration on brain uptake of selected compounds.	2001 Jul	11496955
Establishment of the transformants expressing human cytochrome P450 subtypes in HepG2, and their applications on drug metabolism and toxicology.	2001 Jun	11377097
Effect of capillary efflux transport inhibition on the determination of probe recovery during in vivo microdialysis in the brain.	2001 Jun	11356921
In vitro stimulation of warfarin metabolism by quinidine: increases in the formation of 4'- and 10-hydroxywarfarin.	2001 Jun	11353757
Mechanism-based inactivation of CYP2D6 by 5-fluoro-2-[4-[(2-phenyl-1H-imidazol-5-yl)methyl]-1-piperazinyl]pyrimidine.	2001 Jun	11353755
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy.	2001 Mar	11324359
Capillary electrophoretic separation, immunochemical recognition and analysis of the diastereomers quinine and quinidine and two quinidine metabolites in body fluids.	2001 Mar	11248471
Ascorbic acid-induced modulation of venous tone in humans.	2001 Mar	11244023
Acute canine model for drug-induced Torsades de Pointes in drug safety evaluation-influences of anesthesia and validation with quinidine and astemizole.	2001 Mar	11222883
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels.	2001 Mar 23	11263999
Metabolism of amiodarone (Part III): identification of rabbit cytochrome P450 isoforms involved in the hydroxylation of mono-N-desethylamiodarone.	2001 May	11491386
Mechanical effects of liriodenine on the left ventricular-arterial coupling in Wistar rats: pressure-stroke volume analysis.	2001 May	11325791
Metabolism of sulfinpyrazone sulfide and sulfinpyrazone by human liver microsomes and cDNA-expressed cytochrome P450s.	2001 May	11302937
Effect of P-glycoprotein on flavopiridol sensitivity.	2001 May 18	11355953
Evaluation of the contribution to enantioselectivity of quinine and quinidine scaffolds in chemically and physically mixed chiral selectors.	2001 May 5	11284022
Inhibition of cytochrome P4502D6 activity with paroxetine normalizes the ultrarapid metabolizer phenotype as measured by nortriptyline pharmacokinetics and the debrisoquin test.	2001 Oct	11673748
GAT2/BGT-1 as a system responsible for the transport of gamma-aminobutyric acid at the mouse blood-brain barrier.	2001 Oct	11598501
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.	2001 Oct	11582539
In vitro metabolism of tegaserod in human liver and intestine: assessment of drug interactions.	2001 Oct	11560869
Different enantioselective 9-hydroxylation of risperidone by the two human CYP2D6 and CYP3A4 enzymes.	2001 Oct	11560868
Alkaline phosphatase from rat liver and kidney is differentially modulated.	2001 Sep	11676975
Development of stereoselective nonaqueous capillary electrophoresis system for the resolution of cationic and amphoteric analytes.	2001 Sep	11589294
Quinidine induced electrocardiographic normalization in two patients with Brugada syndrome.	2001 Sep	11584468
Multidrug resistance-associated protein-1 functional activity in Calu-3 cells.	2001 Sep	11504821
Three thiadiazinone derivatives, EMD 60417, EMD 66430, and EMD 66398, with class III antiarrhythmic activity but different electrophysiologic profiles.	2001 Sep	11486248
Purinoreceptors are involved in the control of acute morphine withdrawal.	2001 Sep 21	11669461

Patents

Sample Use Guides

In Vivo Use Guide

Tablet (sulfate):100 to 600 mg/dose orally every 4 to 6 hours; begin at 200 mg/dose and titrate to desired effect (maximum daily dose: 3 to 4 g). Extended Release: 324 to 648 mg (gluconate) orally every 8 to 12 hours or 300 to 600 mg (sulfate) orally every 8 to 12 hours. IV: 800 mg of quinidine gluconate diluted to 50 mL and given at a rate not to exceed 1 mL/min.

Route of Administration: Other

In Vitro Use Guide

Rat brain pericytes were plated onto the backside of 12-well Transwell filters (pore size: 0.4 μm; 1.5 × 104 cells/filter). The next day, endothelial cells were plated onto the upper surface of the filters. After reaching confluency, the endothelial monolayer was supplied with 550 nM hydrocortisone, 250 μM CPT-cAMP, and 17.5 μM RO-201724 and placed into dishes containing glial cultures for 24 h. Transwell filters containing endothelial cells and pericytes were removed from the plates containing the glial culture. Filters were washed with Ringer-HEPES solution (pH 7.4). Quinidine or digoxin was applied at final concentrations of 0.1 μM and 10 μM, respectively. Radiolabeled quinidine and digoxin as tracers were also added to the radioactive concentration of 1 μCi/mL. The inhibitors were added together with the test compound at final concentrations of 1 μM (LY- 335979 and PSC-833) or 100 μM (quinidine). Samples were taken from the basolateral or apical side, respectively, at 15, 30, and 60 min, and radioactivity was measured using a liquid scintillation counter

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:01:39 GMT 2023` Edited by `admin` on `Fri Dec 15 15:01:39 GMT 2023`
Record UNII	S4P5V5597B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUINIDINE HYDROCHLORIDE

Common Name

English

Quinidine hydrochloride [WHO-DD]

Common Name

English

CINCHONAN-9-OL, 6'-METHOXY-, HYDROCHLORIDE (1:1), (9S)-

Common Name

English

Code System Code Type Description

PUBCHEM

11639099