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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26N2O2.ClH
Molecular Weight 362.894
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROQUINIDINE HYDROCHLORIDE

SMILES

Cl.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=MULXTQKDWYBJMO-VJAUXQICSA-N
InChI=1S/C20H26N2O2.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;/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3;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 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
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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 32.0 nM [IC50]
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Lentoquine

Approved Use

Indications: arrhythmias
Curative
Preclinical
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
activator
150
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OATP1B3
961

OATP1B1
1079
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OATP1B1
1095
 yes [Inhibition 10 uM]
OATP1B3
970
 yes [Inhibition 10 uM]
CYP2D6
2546
 yes [Ki 0.013 uM]
CYP3A4
2633
 yes [Km 100 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
PubMed

PubMed

TitleDatePubMed
The molecular phenotype of endocapillary proliferation: novel therapeutic targets for IgA nephropathy.
2014
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003-09-01
[Adverse drug reactions in three older patients, even without changes in medication].
2003-03-29
Safety and effectiveness of oral quinidine in cardioversion of persistent atrial fibrillation.
2001-12
[Hepatitis caused by quinidine. Study of a case and review of the literature].
1986-03
Patents

Patents

CA2081343A1
2
US3862123
2
US5635515
2

Sample Use Guides

In Vivo Use Guide
500 mg/12 h mg daily
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Recordings were made from acutely dissociated melanotrophs, obtained following the enzymatic treatment and mechanical disruption of the neuro-intermediate lobe of the pituitary gland of the adult male rat
Halfmaximal inhibition of IK(f) at o mV occurred with 23 + 7.8uM hydroquinidine
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:01:14 GMT 2025
Edited
by admin
on Mon Mar 31 19:01:14 GMT 2025
Record UNII
6BR4G8VAHM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SERECOR
Preferred Name English
HYDROQUINIDINE HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
Hydroquinidine hydrochloride [WHO-DD]
Common Name English
HYDROQUINIDINE HCL
Common Name English
(9S)-10,11-DIHYDRO-6'-METHOXYCINCHONAN-9-OL HYDROCHLORIDE
Common Name English
HYDROCONCHININE HYDROCHLORIDE
Common Name English
HYDROQUINIDINE HYDROCHLORIDE [MI]
Common Name English
HYDROQUINIDINE HYDROCHLORIDE [MART.]
Common Name English
Code System Code Type Description
PUBCHEM
16211709
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY
ECHA (EC/EINECS)
216-024-1
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY
FDA UNII
6BR4G8VAHM
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY
CAS
1476-98-8
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY
MESH
C014486
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY
EVMPD
SUB14137MIG
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID00933162
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY
SMS_ID
100000077619
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY
RXCUI
236160
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m6113
Created by admin on Mon Mar 31 19:01:14 GMT 2025 , Edited by admin on Mon Mar 31 19:01:14 GMT 2025
PRIMARY Merck Index
Related Record Type Details
Structure of HYDROQUINIDINE
PARENT -> SALT/SOLVATE
NIH
NCATS
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