U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O2
Molecular Weight 324.4168
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE

SMILES

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

InChI

InChIKey=LOUPRKONTZGTKE-WZBLMQSHSA-N
InChI=1S/C20H24N2O2/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/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H24N2O2
Molecular Weight 324.4168
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 http://www.fda.gov/downloads/ForHealthProfessionals/LearningActivities/UCM317816.pdf

Quinine soluble salts possess the extremely bitter taste, that may have a perplexing problem especially to children. That is why the most common combinations which are administered in this way are the sulphate, salicylate, tannate and certain esters. Quinine tannate, an insoluble quinine salt has been known in medicine for a very long time. However, many experiments have revealed that quinine tannate was practically inert as a medicinal substance.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
QUALAQUIN

Approved Use

is a cinchona alkaloid indicated for treatment of uncomplicated Plasmodium falciparum malaria

Launch Date

1.12380477E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.2 μg/mL
8.7 mg/kg single, oral
dose: 8.7 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUININE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
28 μg × h/mL
8.7 mg/kg single, oral
dose: 8.7 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUININE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.5 h
8.7 mg/kg single, oral
dose: 8.7 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUININE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
8%
8.7 mg/kg single, oral
dose: 8.7 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUININE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 g single, oral
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: M
Population Size: 1
Sources:
Other AEs: Respiratory distress...
Other AEs:
Respiratory distress (grade 5, 1 patient)
Sources:
1.8 g single, oral
Overdose
Dose: 1.8 g
Route: oral
Route: single
Dose: 1.8 g
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Age Group: 46 years
Sex: F
Population Size: 1
Sources:
Other AEs: Hearing loss...
Other AEs:
Hearing loss (1 patient)
Sources:
16250 mg single, oral
Overdose
Dose: 16250 mg
Route: oral
Route: single
Dose: 16250 mg
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Other AEs: Cardiotoxicity...
Other AEs:
Cardiotoxicity (1 patient)
Sources:
9.75 g single, oral
Dose: 9.75 g
Route: oral
Route: single
Dose: 9.75 g
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Sex: M
Population Size: 1
Sources:
Other AEs: Tachycardia...
Other AEs:
Tachycardia (grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Respiratory distress grade 5, 1 patient
5 g single, oral
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: M
Population Size: 1
Sources:
Hearing loss 1 patient
1.8 g single, oral
Overdose
Dose: 1.8 g
Route: oral
Route: single
Dose: 1.8 g
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Age Group: 46 years
Sex: F
Population Size: 1
Sources:
Cardiotoxicity 1 patient
16250 mg single, oral
Overdose
Dose: 16250 mg
Route: oral
Route: single
Dose: 16250 mg
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Age Group: 49 years
Sex: F
Population Size: 1
Sources:
Tachycardia grade 5
9.75 g single, oral
Dose: 9.75 g
Route: oral
Route: single
Dose: 9.75 g
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Sex: M
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Drug-induced thrombotic microangiopathy: incidence, prevention and management.
2001
Quinine-induced alterations of electrically evoked otoacoustic emissions and cochlear potentials in guinea pigs.
2001 Apr
Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector.
2001 Apr
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.
2001 Apr
Use of the DELI-microtest to determine the drug sensitivity of Plasmodium falciparum in Burkina Faso.
2001 Apr
The first stereoselective total synthesis of quinine.
2001 Apr 11
[Plasmodium vivax: therapy update].
2001 Apr 21
Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate.
2001 Apr 27
In vitro antiplasmodial activity of 4-phenylcoumarins from Exostema mexicanum.
2001 Feb
Delayed quinine toxicity mimicking open angle glaucoma.
2001 Feb
BK channels in human glioma cells.
2001 Feb
Adrenocorticotropic hormone activates an outward current in cultured mouse peritoneal macrophages.
2001 Feb 15
Uptake properties of lamivudine (3TC) by a continuous renal epithelial cell line.
2001 Jan
Comparative expression of hedonic impact: affective reactions to taste by human infants and other primates.
2001 Jan
Babesiosis.
2001 Jan
Evaluation of a vincristine resistant Caco-2 cell line for use in a calcein AM extrusion screening assay for P-glycoprotein interaction.
2001 Jan
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells.
2001 Jul
Sapid solutions and food intake in repeated dehydration and rehydration periods in rats.
2001 Jul
Distribution of gustatory sensitivities in rat taste cells: whole-cell responses to apical chemical stimulation.
2001 Jul 1
Polyvinyl chloride-based membranes for flow injection analysis of quinine in beverages.
2001 Jul-Aug
Influence of quinine on catecholamine release evoked by cholinergic stimulation and membrane depolarization from the rat adrenal gland.
2001 Jun
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada.
2001 Jun 12
[Photodermatosis induced by hydroxychloroquine: 4 cases].
2001 Jun-Jul
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy.
2001 Mar
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels.
2001 Mar 23
[Severe malaria].
2001 Mar 31
Hyperpolarizing shift by quinine in the steady-state inactivation curve of delayed rectifier-type potassium current in bullfrog sympathetic neurons.
2001 Mar 9
Exchange transfusion for severe malaria.
2001 Mar-Apr
Oral quinine pharmacokinetics and dietary salt intake.
2001 May
Effect of compound sequence on bitterness enhancement.
2001 May
Volume-activated trimethylamine oxide efflux in red blood cells of spiny dogfish (Squalus acanthias).
2001 Sep
Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1.
2001 Sep
HPLC of basic drugs on microparticulate strong cation-exchange materials - a review.
2001 Sep 15
Properties and regulation of organic cation transport in freshly isolated human proximal tubules.
2001 Sep 7
Patents

Sample Use Guides

in adults: 648 mg (two capsules) every 8 hours for 7 days
Route of Administration: Oral
Quinine (0-100 uM) stimulates adipogenesis through ERK/S6 (extracellular-signal-regulated kinase/Ribosomal protein S6) signaling, which at least partly functions via taste receptor, type 2, member 106 (T2R106)
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:32:52 UTC 2022
Edited
by admin
on Fri Dec 16 16:32:52 UTC 2022
Record UNII
A7V27PHC7A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUININE
HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
QUININE [MI]
Common Name English
QUININE [HSDB]
Common Name English
Quinine [WHO-DD]
Common Name English
QUININE [MART.]
Common Name English
REZQUIN
Common Name English
WR297608
Code English
CHININUM PURUM [HPUS]
Common Name English
(8S,9R)-6'-METHOXYCINCHONAN-9-OL
Common Name English
QUININE [VANDF]
Common Name English
QUALAQUIN
Common Name English
NSC-192949
Code English
QUININE [INCI]
Common Name English
CHININUM PURUM
HPUS  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C271
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
WHO-ATC P01BC01
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
CFR 21 CFR 862.3750
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
CFR 21 CFR 310.546
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
DSLD 2588 (Number of products:3)
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
CFR 21 CFR 172.575
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
CFR 21 CFR 310.547
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
NDF-RT N0000175482
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
WHO-VATC QM09AA72
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
WHO-ATC M09AA72
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
LIVERTOX NBK548596
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
Code System Code Type Description
CHEBI
15854
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
CHEBI
137041
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
CHEBI
52251
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
DAILYMED
A7V27PHC7A
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
DRUG CENTRAL
4523
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
FDA UNII
A7V27PHC7A
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
MESH
D011803
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
LACTMED
Quinine
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
IUPHAR
2510
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
ChEMBL
CHEMBL170
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
NSC
192949
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
WIKIPEDIA
QUININE
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
ECHA (EC/EINECS)
205-003-2
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
HSDB
2501
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
RXCUI
9071
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY RxNorm
CAS
130-95-0
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
NCI_THESAURUS
C794
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
DRUG BANK
DB00468
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
MERCK INDEX
M9447
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY Merck Index
EVMPD
SUB15084MIG
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
PUBCHEM
3034034
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
EPA CompTox
DTXSID0044280
Created by admin on Fri Dec 16 16:32:53 UTC 2022 , Edited by admin on Fri Dec 16 16:32:53 UTC 2022
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
PLASMA; URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
MINOR
PLASMA; URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE LESS ACTIVE -> PARENT
MAJOR
PLASMA; URINE
METABOLITE LESS ACTIVE -> PARENT
Quinine is metabolized almost exclusively via hepatic oxidative cytochrome P450 (CYP) pathways. In vitro studies using human liver microsomes and recombinant P450 enzymes have shown that quinine is metabolized mainly by CYP3A4. Depending on the in vitro experimental conditions, other enzymes, including CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP2E1 were shown to have some role in the metabolism of quinine.
METABOLITE -> PARENT
MINOR
PLASMA; URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC