HYDROQUINIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H26N2O2
Molecular Weight	326.4326
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LJOQGZACKSYWCH-LHHVKLHASA-N

InChI=1S/C20H26N2O2/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/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19+,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H26N2O2
Molecular Weight	326.4326
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/international/hydroquinidine.html | http://drugs-about.com/drugs-l/lentoquine.html | https://books.google.ru/books?id=9sYlCQAAQBAJ&pg=PA1114&lpg=PA1114&dq=HYDROQUINIDINE
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24068450 http://www.ajtmh.org/content/s1-12/6/473.full.pdf

Hydroquinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent (Ia) in the heart. Hydroquinidine is a d-rotatory alkaloid derived from cinchiona bark. It is closely related to quinidine, differing from the latter alkaloid only in containing two more atoms of hydrogen in the molecule. The drug causes increased action potential duration, as well as a prolonged QT interval. It is not approved by FDA, but marketed in Spain, France, Italy and Pakistan under the brand names Lentoquine, Sérécor LP, Idrochinidina Lirca and Austacute, respectively. Like all other class I antiarrhythmic agents, Hydroquinidine primarily works by blocking the fast inward sodium current (INa). Hydroquinidine is also used for the treatment of Malaria.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Plasmodium falciparum 75 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22869567	Inhibitor 8504		32.0 nM [IC50]
Sodium channel alpha subunit 72 Target ID: CHEMBL2331043 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D08048 \| https://www.ncbi.nlm.nih.gov/pubmed/22766342 \| https://books.google.ru/books?id=9sYlCQAAQBAJ&pg=PA1114&lpg=PA1114&dq=HYDROQUINIDINE	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Arrhythmia 45 Sources: https://www.drugs.com/international/hydroquinidine.html http://www.ndrugs.com/?s=hydroquinidine http://drugs-about.com/drugs-l/lentoquine.html	Primary		Approved 8583	Lentoquine Approved Use Indications: arrhythmias
Malaria 96 Sources: http://www.ajtmh.org/content/s1-12/6/473.full.pdf	Curative		Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.74 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7095920/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROQUINIDINE unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.55 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7095920/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROQUINIDINE unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7095920/	300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered:		HYDROQUINIDINE unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10938184/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10938184/	Disc. AE: Nausea, Epigastric pain... AEs leading to discontinuation/dose reduction: Nausea (25%) Epigastric pain (25%) Sources: https://pubmed.ncbi.nlm.nih.gov/10938184/
738 mg 1 times / day multiple, oral Studied dose Dose: 738 mg, 1 times / day Route: oral Route: multiple Dose: 738 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/	Disc. AE: Gastrointestinal disorder, Photophobia... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder (20%) Photophobia (4%) Photosensitivity (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/

AEs

AE	Significance	Dose	Population
Epigastric pain	25% Disc. AE	150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10938184/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10938184/
Nausea	25% Disc. AE	150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10938184/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10938184/
Photosensitivity	2% Disc. AE	738 mg 1 times / day multiple, oral Studied dose Dose: 738 mg, 1 times / day Route: oral Route: multiple Dose: 738 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/
Gastrointestinal disorder	20% Disc. AE	738 mg 1 times / day multiple, oral Studied dose Dose: 738 mg, 1 times / day Route: oral Route: multiple Dose: 738 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/
Photophobia	4% Disc. AE	738 mg 1 times / day multiple, oral Studied dose Dose: 738 mg, 1 times / day Route: oral Route: multiple Dose: 738 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28411139/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 150		inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 961 OATP1B1 1079	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE5MDY4OTAifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE5MDY4OTAifX0=	yes [Inhibition 10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/7575645/	yes [Ki 0.013 uM]
CYP3A4 2633	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/10381752/	yes [Km 100 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/91503#section=Biological-Test-Results Page: 8 \| 12	no

PubMed

Title	Date	PubMed
[Hepatitis caused by quinidine. Study of a case and review of the literature].	1986 Mar	3732735
Safety and effectiveness of oral quinidine in cardioversion of persistent atrial fibrillation.	2001 Dec	11806093
[Adverse drug reactions in three older patients, even without changes in medication].	2003 Mar 29	12701389
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.	2003 Sep 1	14505493
The molecular phenotype of endocapillary proliferation: novel therapeutic targets for IgA nephropathy.	2014	25133636

Patents

Sample Use Guides

In Vivo Use Guide

500 mg/12 h mg daily

Route of Administration: Oral

In Vitro Use Guide

Halfmaximal inhibition of IK(f) at o mV occurred with 23 + 7.8uM hydroquinidine

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:47:52 GMT 2025` Edited by `admin` on `Mon Mar 31 18:47:52 GMT 2025`
Record UNII	8P68XPY4HG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(9S)-10,11-DIHYDRO-6'-METHOXYCINCHONAN-9-OL

Preferred Name

English

HYDROQUINIDINE

Common Name

English

Hydroquinidine [WHO-DD]

Common Name

English

NSC-757410

Code

English

HYDROQUINIDINE [MI]

Common Name

English

DIHYDROQUINIDINE

Common Name

English

HYDROCONCHININE

Common Name

English

Classification Tree Code System Code

WHO-ATC

C01BA13