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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C20H24N2O2.C6H8O7
Molecular Weight 840.957
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE CITRATE

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=CC=C2N=CC=C([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)C2=C1.COC5=CC=C6N=CC=C([C@@H](O)[C@@H]7C[C@@H]8CC[N@]7C[C@@H]8C=C)C6=C5

InChI

InChIKey=YSFIPRFOHJQXJF-VMJVVOMYSA-N
InChI=1S/2C20H24N2O2.C6H8O7/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;7-3(8)1-6(13,5(11)12)2-4(9)10/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t2*13-,14-,19-,20+;/m00./s1

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

2005
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
Health Status: unhealthy
Age Group: 17 years
Sex: M
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
Health Status: unhealthy
Age Group: 46 years
Sex: F
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
Health Status: unhealthy
Age Group: 49 years
Sex: F
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
Health Status: unhealthy
Age Group: adult
Sex: M
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
Health Status: unhealthy
Age Group: 17 years
Sex: M
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
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Cardiotoxicity 1 patient
16250 mg single, oral
Overdose
Dose: 16250 mg
Route: oral
Route: single
Dose: 16250 mg
Sources:
unhealthy, 49 years
Health Status: unhealthy
Age Group: 49 years
Sex: F
Sources:
Tachycardia grade 5
9.75 g single, oral
Dose: 9.75 g
Route: oral
Route: single
Dose: 9.75 g
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
PubMed

PubMed

TitleDatePubMed
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
Simultaneous determination of quinine and four metabolites in plasma and urine by high-performance liquid chromatography.
2001 Apr 15
Resurgence of blackwater fever in long-term European expatriates in Africa: report of 21 cases and review.
2001 Apr 15
Severe babesiosis in Long Island: review of 34 cases and their complications.
2001 Apr 15
Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate.
2001 Apr 27
Quinine-induced thrombocytopenia in a 64-year-old man who consumed tonic water to relieve nocturnal leg cramps.
2001 Aug
Ferrocene-chloroquine analogues as antimalarial agents: in vitro activity of ferrochloroquine against 103 Gabonese isolates of Plasmodium falciparum.
2001 Aug
Pontine gustatory activity is altered by electrical stimulation in the central nucleus of the amygdala.
2001 Feb
Activation of ion-conducting pathways in the inner mitochondrial membrane - an unrecognized activity of fatty acid?
2001 Feb 23
Taste receptor cells that discriminate between bitter stimuli.
2001 Feb 23
Declining chloroquine resistance of Plasmodium falciparum in Lambaréné, Gabon from 1992 to 1998.
2001 Jan 15
Effect of extracellular Ca2+ on the quinine-activated current of bullfrog taste receptor cells.
2001 Jan 15
The applicability of rat and human liver slices to the study of mechanisms of hepatic drug uptake.
2001 Jan-Feb
[Effect of antibodies against S100 proteins on neural plasticity in sensitized and naive snails].
2001 Jan-Feb
Distribution of gustatory sensitivities in rat taste cells: whole-cell responses to apical chemical stimulation.
2001 Jul 1
Therapeutic efficacy of sulphadoxine/pyrimethamine and susceptibility in vitro of P. falciparum isolates to sulphadoxine-pyremethamine and other antimalarial drugs in Malawian children.
2001 Jun
A comparison of brain, core and skin temperature in children with complicated and uncomplicated malaria.
2001 Jun
Nocturnal leg cramps. Clinically mysterious and painful--but manageable.
2001 Jun
Mechanisms by which intracellular calcium induces susceptibility to secretory phospholipase A2 in human erythrocytes.
2001 Jun 22
Effects of hydroxypyridinone iron chelators in combination with antimalarial drugs on the in vitro growth of Plasmodium falciparum.
2001 Mar
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy.
2001 Mar
Capillary electrophoretic separation, immunochemical recognition and analysis of the diastereomers quinine and quinidine and two quinidine metabolites in body fluids.
2001 Mar
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels.
2001 Mar 23
Exchange transfusion for severe malaria.
2001 Mar-Apr
Oral quinine pharmacokinetics and dietary salt intake.
2001 May
Changes in taste intensity perception following anterior temporal lobe removal in humans.
2001 May
Evaluation of the contribution to enantioselectivity of quinine and quinidine scaffolds in chemically and physically mixed chiral selectors.
2001 May 5
Is multiple sclerosis caused by a silent infection with malarial parasites? A historico-epidemiological approach: part II.
2001 Sep
Volume-activated trimethylamine oxide efflux in red blood cells of spiny dogfish (Squalus acanthias).
2001 Sep
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 Mon Mar 31 17:51:04 GMT 2025
Edited
by admin
on Mon Mar 31 17:51:04 GMT 2025
Record UNII
L8D5LFU229
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUININE CITRATE
WHO-DD  
Common Name English
CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9R)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (2:1) (SALT)
Preferred Name English
Quinine citrate [WHO-DD]
Common Name English
QUININE, CITRATE (2:1) (SALT)
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.547
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
Code System Code Type Description
PUBCHEM
71586768
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
PRIMARY
DRUG BANK
DBSALT002255
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
PRIMARY
FDA UNII
L8D5LFU229
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
PRIMARY
SMS_ID
100000078601
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
PRIMARY
EVMPD
SUB15089MIG
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
PRIMARY
CAS
752-72-7
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID10226178
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
PRIMARY
ECHA (EC/EINECS)
212-037-1
Created by admin on Mon Mar 31 17:51:04 GMT 2025 , Edited by admin on Mon Mar 31 17:51:04 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY