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

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O2
Molecular Weight 324.4175
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE

SMILES

C=C[C@@]1([H])CN2CC[C@@]1([H])C[C@@]2([H])[C@@]([H])(c3ccnc4ccc(cc34)OC)O

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 324.4175
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

QUALAQUIN (quinine sulfate) is an antimalarial drug indicated only for treatment of uncomplicated Plasmodium falciparum malaria. It’s an alkaloid derived from the bark of the cinchona tree and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine sulfate has been shown to be effective in geographical regions where resistance to chloroquine has been documented. Quinine inhibits nucleic acid synthesis, protein synthesis, and glycolysis in Plasmodium falciparum and can bind with hemazoin in parasitized erythrocytes. However, the precise mechanism of the antimalarial activity of quinine sulfate is not completely understood. It is thought to act by inhibiting heme polymerase, thereby allowing accumulation of its cytotoxic substrate, heme. As a schizonticidal drug, it is less effective and more toxic than chloroquine. Quinine is FDA-approved. It is not considered safe and effective for the treatment or prevention of leg cramps-- an "off-label" (non-FDA-approved) use. Quinine is associated with serious and life-threatening adverse events, including: thrombocytopenia, hypersensitivity reactions, and QT prolongation. Thrombocytopenia associated with the use of quinine for the treatment or prevention of leg cramps includes: immune thrombocytopenic purpura, hemolytic uremic syndrome, thrombotic thrombocytepenic purpura with associated renal insufficiency.

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
Olfactory learning induces differential long-lasting changes in rat central olfactory pathways.
2001
Quinine-induced alterations of electrically evoked otoacoustic emissions and cochlear potentials in guinea pigs.
2001 Apr
Use of the DELI-microtest to determine the drug sensitivity of Plasmodium falciparum in Burkina Faso.
2001 Apr
Muscimol infusions in the brain stem reticular formation reversibly block ingestion in the awake rat.
2001 Apr
Severe babesiosis in Long Island: review of 34 cases and their complications.
2001 Apr 15
[Plasmodium vivax: therapy update].
2001 Apr 21
Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate.
2001 Apr 27
5-HT1A receptor-mediated activation of G-protein-gated inwardly rectifying K+ current in rat periaqueductal gray neurons.
2001 Aug
Role of quinine-sensitive ion channels in volume regulation in boar and bull spermatozoa.
2001 Aug
Large-conductance calcium-activated potassium channels in neonatal rat intracardiac ganglion neurons.
2001 Feb
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
Pontine gustatory activity is altered by electrical stimulation in the central nucleus of the amygdala.
2001 Feb
Ethanol perception and ingestion.
2001 Jan
Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates.
2001 Jan 1
Evaluation under field conditions of the colourimetric DELI-microtest for the assessment of Plasmodium falciparum drug resistance.
2001 Jan-Feb
Changing epidemiological and clinical aspects of imported malaria in Belgium.
2001 Jan-Feb
Apparent drug failure following artesunate treatment of Plasmodium falciparum malaria in Freetown, Sierra Leone: four case reports.
2001 Jul
Simultaneous determination of etoposide and its catechol metabolite in the plasma of pediatric patients by liquid chromatography/tandem mass spectrometry.
2001 Jul
Myosin II-dependent cylindrical protrusions induced by quinine in Dictyostelium: antagonizing effects of actin polymerization at the leading edge.
2001 Jun
Lateral parabrachial nucleus lesions in the rat: neophobia and conditioned taste aversion.
2001 Jun
The effect of laser assisted uvulopalatoplasty on the sense of smell and taste.
2001 Jun
Nocturnal leg cramps. Clinically mysterious and painful--but manageable.
2001 Jun
[Photodermatosis induced by hydroxychloroquine: 4 cases].
2001 Jun-Jul
[Treatment of acute malaria with quinine in a non-immunized patient: rationale for a 7-day regimen].
2001 Mar 17
[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
Molecular cloning and characterization of a novel (Na+,K+)/H+ exchanger localized to the trans-Golgi network.
2001 May 18
Is multiple sclerosis caused by a silent infection with malarial parasites? A historico-epidemiological approach: part II.
2001 Sep
Antimalarial activity of azithromycin, artemisinin and dihydroartemisinin in fresh isolates of Plasmodium falciparum in Thailand.
2001 Sep 1
Septic shock due to babesiosis.
2001 Sep 1
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 Sat Jun 26 08:47:30 UTC 2021
Edited
by admin
on Sat Jun 26 08:47:30 UTC 2021
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 [MART.]
Common Name English
QUININE [WHO-DD]
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 Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
WHO-ATC P01BC01
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
CFR 21 CFR 862.3750
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
CFR 21 CFR 310.546
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
DSLD 2588 (Number of products:3)
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
CFR 21 CFR 172.575
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
CFR 21 CFR 310.547
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
NDF-RT N0000175482
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
WHO-VATC QM09AA72
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
WHO-ATC M09AA72
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
LIVERTOX 826
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
Code System Code Type Description
DRUG CENTRAL
4523
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
FDA UNII
A7V27PHC7A
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
MESH
D011803
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
LACTMED
Quinine
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
IUPHAR
2510
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
ChEMBL
CHEMBL170
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
WIKIPEDIA
QUININE
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-003-2
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
HSDB
2501
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
RXCUI
9071
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY RxNorm
CAS
130-95-0
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
NCI_THESAURUS
C794
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
DRUG BANK
DB00468
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
MERCK INDEX
M9447
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY Merck Index
EVMPD
SUB15084MIG
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
PUBCHEM
3034034
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
EPA CompTox
130-95-0
Created by admin on Sat Jun 26 08:47:31 UTC 2021 , Edited by admin on Sat Jun 26 08:47:31 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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
TRANSPORTER -> INHIBITOR
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