U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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 of HYDROQUININE

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
129.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Inhibin
Curative
Unknown
Primary
Hydroquinine

Cmax

ValueDoseCo-administeredAnalytePopulation
2.43 mg/L
300 mg single, oral
HYDROQUININE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
29.7 mg × h/L
300 mg single, oral
HYDROQUININE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10.9 h
300 mg single, oral
HYDROQUININE serum
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
31J3Q51T6L
Record Status Validated (UNII)
Record Version