HYDROQUININE

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-WZBLMQSHSA-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: http://databankws.lareb.nl/Downloads/KWB_2014_2_hydro.pdf | http://www.tabletwise.com/medicine/hydroquinine | http://skinwhiteningnews.org/dangers-of-skin-whitening/
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/international/hydroquinine.html http://www.genome.jp/dbget-bin/www_bget?dr:D08265

Hydroquinine (Inhibin®) has been approved for marketing in the Netherlands for the treatment of nocturnal cramps when treatment with drugs is considered necessary. It is available in the Netherlands since March 1990 as an over-the-counter drug with a dose of 200 mg with the evening meal and a further 100 mg at bedtime for 14 days. Hydroquinine also has antimalarial and demelanizing activity. It might be used to lightens light brown color patches on skin, age spots, skin discolorations associated with pregnancy, skin trauma or taking birth control pills. Hydroquinine is used in skin lightening creams and lotions because it is an effective bleaching agent, slowing the production of the tyrosinase enzyme and reducing the amount of melanin formed.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Plasmodium falciparum 75 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22869567 \| https://www.ncbi.nlm.nih.gov/pubmed/8944272	Inhibitor 8504		129.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Nocturnal cramps 3 Sources: http://databankws.lareb.nl/Downloads/KWB_2014_2_hydro.pdf http://www.hdcn.com/7/702lajan.htm	Primary	Approved 8583	Inhibin Approved Use Hydroquinine hydrobromide (Inhibin®) has been approved for marketing in the Netherlands for the treatment of nocturnal cramps when treatment with drugs is considered necessary. Launch Date 1990
Malaria 96 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22869567 https://www.ncbi.nlm.nih.gov/pubmed/8944272	Curative	Preclinical	Unknown Approved Use Unknown
Skin hyperpigmentation 5 Sources: http://www.tabletwise.com/medicine/hydroquinine	Primary	Approved 8583	Hydroquinine Approved Use Hydroquinine is used for the treatment, control, prevention, and improvement of the following diseases, conditions and symptoms: Lightens light brown color patches on skin Age spots Skin discolorations associated with pregnancy Skin trauma Birth control pills Hormone replacement therapy during menopause

C_max

Value	Dose	Co-administered	Analyte	Population
2.43 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952483/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROQUININE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
29.7 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952483/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROQUININE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952483/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROQUININE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
590 mg single, oral Accidental dose Dose: 590 mg Route: oral Route: single Dose: 590 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/	Other AEs: Headache, Vertigo... Other AEs: Headache Vertigo Sleepiness Photophobia Tachycardia Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/
300 mg 3 times / day multiple, oral Highest studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/	Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/
300 mg 3 times / day multiple, oral Highest studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8745663/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8745663/	Disc. AE: Ventricular tachycardia... AEs leading to discontinuation/dose reduction: Ventricular tachycardia (2.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/8745663/
600 mg single, oral Highest studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/	Other AEs: Hypotension, Light-headed feeling... Other AEs: Hypotension (7%) Light-headed feeling (7%) Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/

AEs

AE	Significance	Dose	Population
Headache		590 mg single, oral Accidental dose Dose: 590 mg Route: oral Route: single Dose: 590 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/
Photophobia		590 mg single, oral Accidental dose Dose: 590 mg Route: oral Route: single Dose: 590 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/
Sleepiness		590 mg single, oral Accidental dose Dose: 590 mg Route: oral Route: single Dose: 590 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/
Tachycardia		590 mg single, oral Accidental dose Dose: 590 mg Route: oral Route: single Dose: 590 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/
Vertigo		590 mg single, oral Accidental dose Dose: 590 mg Route: oral Route: single Dose: 590 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7273674/
Ventricular tachycardia	2.3% Disc. AE	300 mg 3 times / day multiple, oral Highest studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8745663/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8745663/
Hypotension	7%	600 mg single, oral Highest studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/
Light-headed feeling	7%	600 mg single, oral Highest studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/2484920/

PubMed

Title	Date	PubMed
Antimalarial activity and interactions between quinine, dihydroquinine and 3-hydroxyquinine against Plasmodium falciparum in vitro.	1996-09-01	8944272

Patents

Sample Use Guides

In Vivo Use Guide

200 mg with the evening meal and a further 100 mg at bedtime for 14 days

Route of Administration: Oral

In Vitro Use Guide

The median inhibitory concentration (IC50) for hydroquinine against Plasmodium falciparum in vitro was 129 nmol/L (range 54-324)

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:12:40 GMT 2025` Edited by `admin` on `Mon Mar 31 20:12:40 GMT 2025`
Record UNII	31J3Q51T6L
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DIHYDROQUININE

Preferred Name

English

HYDROQUININE

Common Name

English

NSC-41799

Code

English

QUININE HYDROCHLORIDE IMPURITY C [EP IMPURITY]

Common Name

English

HYDROQUININE [MI]

Common Name

English

DIHYDROQUININE [WHO-IP]

Common Name

English

Hydroquinine [WHO-DD]

Common Name

English

QUINIDINE SULFATE IMPURITY C [WHO-IP]

Common Name

English

(-)-HYDROQUININE

Common Name

English

QUININE SULFATE IMPURITY C [EP IMPURITY]

Common Name

English

10,11-DIHYDROQUININE

Common Name

English

(R)-((2S,4S,5R)-5-ETHYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(6-METHOXYQUINOLIN-4-YL)METHANOL [WHO-IP]

Systematic Name

English

QUININE BISULFATE HEPTAHYDRATE IMPURITY C [WHO-IP]

Common Name

English

CINCHONAN-9-OL, 10,11-DIHYDRO-6'-METHOXY-, (8.ALPHA.,9R)-

Common Name

English

(8.ALPHA.,9R)-10,11-DIHYDRO-6'-METHOXYCINCHONAN-9-OL

Systematic Name

English

QUININE BISULFATE IMPURITY C [WHO-IP]

Common Name

English

(-)-10,11-DIHYDROQUININE

Common Name

English

Classification Tree Code System Code

WHO-ATC

M09AA01