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

[H][C@@]1(C[C@@H]2CC[N@]1C[C@@H]2CC)[C@@H](O)C3=CC=NC4=CC=C(OC)C=C34

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 74 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22869567	Inhibitor 8297		32.0 nM [IC50]
Sodium channel alpha subunit 76 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 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Arrhythmia 38 Sources: https://www.drugs.com/international/hydroquinidine.html http://www.ndrugs.com/?s=hydroquinidine http://drugs-about.com/drugs-l/lentoquine.html	Primary		Approved 8429	Lentoquine Approved Use Indications: arrhythmias
Malaria 95 Sources: http://www.ajtmh.org/content/s1-12/6/473.full.pdf	Curative		Preclinical	Unknown Approved Use Unknown

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 `Fri Dec 15 17:32:18 UTC 2023` Edited by `admin` on `Fri Dec 15 17:32:18 UTC 2023`
Record UNII	8P68XPY4HG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

HYDROQUINIDINE

Common Name

English

Hydroquinidine [WHO-DD]

Common Name

English

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

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