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

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
Drug-induced thrombotic microangiopathy: incidence, prevention and management.
2001
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
Cell volume-induced changes in K+ transport across the rat colon.
2001 Apr
Patterns of Plasmodium falciparum drug resistance in nonimmune travellers to Africa.
2001 Apr
Two procedures establishing preference for oral cocaine and lidocaine solutions which do not use an associative history with a reinforcer.
2001 Apr
Muscimol infusions in the brain stem reticular formation reversibly block ingestion in the awake rat.
2001 Apr
The first stereoselective total synthesis of quinine.
2001 Apr 11
Role of parabrachial nucleus in submandibular salivary secretion induced by bitter taste stimulation in rats.
2001 Apr 12
5-HT1A receptor-mediated activation of G-protein-gated inwardly rectifying K+ current in rat periaqueductal gray neurons.
2001 Aug
Ferrocene-chloroquine analogues as antimalarial agents: in vitro activity of ferrochloroquine against 103 Gabonese isolates of Plasmodium falciparum.
2001 Aug
Role of quinine-sensitive ion channels in volume regulation in boar and bull spermatozoa.
2001 Aug
Reduction of saltiness and bitterness after a chlorhexidine rinse.
2001 Feb
Delayed quinine toxicity mimicking open angle glaucoma.
2001 Feb
Computer-simulation studies on roles of potassium currents in neurotransmission of the auditory nerve.
2001 Feb
Activation of ion-conducting pathways in the inner mitochondrial membrane - an unrecognized activity of fatty acid?
2001 Feb 23
Ethanol perception and ingestion.
2001 Jan
Declining chloroquine resistance of Plasmodium falciparum in Lambaréné, Gabon from 1992 to 1998.
2001 Jan 15
Evaluation under field conditions of the colourimetric DELI-microtest for the assessment of Plasmodium falciparum drug resistance.
2001 Jan-Feb
[Effect of antibodies against S100 proteins on neural plasticity in sensitized and naive snails].
2001 Jan-Feb
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells.
2001 Jul
Simultaneous determination of etoposide and its catechol metabolite in the plasma of pediatric patients by liquid chromatography/tandem mass spectrometry.
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
A comparison of the in vivo kinetics of Plasmodium falciparum ring-infected erythrocyte surface antigen-positive and -negative erythrocytes.
2001 Jul 15
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
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
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada.
2001 Jun 12
[Photodermatosis induced by hydroxychloroquine: 4 cases].
2001 Jun-Jul
Effects of hydroxypyridinone iron chelators in combination with antimalarial drugs on the in vitro growth of Plasmodium falciparum.
2001 Mar
Capillary electrophoretic separation, immunochemical recognition and analysis of the diastereomers quinine and quinidine and two quinidine metabolites in body fluids.
2001 Mar
[Treatment of acute malaria with quinine in a non-immunized patient: rationale for a 7-day regimen].
2001 Mar 17
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels.
2001 Mar 23
[Severe malaria].
2001 Mar 31
The treatment of babesiosis.
2001 Mar 8
Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family.
2001 Mar 9
Oral quinine pharmacokinetics and dietary salt intake.
2001 May
Changes in taste intensity perception following anterior temporal lobe removal in humans.
2001 May
Treatment alternatives for nocturnal leg cramps.
2001 May 21
Resistance of Plasmodium falciparum to antimalarial drugs in a highly endemic area of southern Viet Nam: a study in vivo and in vitro.
2001 May-Jun
A clinical and pharmacokinetic trial of six doses of artemether-lumefantrine for multidrug-resistant Plasmodium falciparum malaria in Thailand.
2001 May-Jun
Clinical trial of beta-arteether versus quinine for the treatment of cerebral malaria in children in Yaounde, Cameroon.
2001 May-Jun
Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1.
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
Optochin resistance in Streptococcus pneumoniae: mechanism, significance, and clinical implications.
2001 Sep 1
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 15 15:13:35 UTC 2023
Edited
by admin
on Fri Dec 15 15:13:35 UTC 2023
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 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
WHO-ATC P01BC01
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
CFR 21 CFR 862.3750
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
CFR 21 CFR 310.546
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
DSLD 2588 (Number of products:3)
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
CFR 21 CFR 172.575
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
CFR 21 CFR 310.547
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
NDF-RT N0000175482
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
WHO-VATC QM09AA72
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
WHO-ATC M09AA72
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
LIVERTOX NBK548596
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
Code System Code Type Description
CHEBI
15854
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
CHEBI
137041
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
CHEBI
52251
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
DAILYMED
A7V27PHC7A
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
DRUG CENTRAL
4523
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
FDA UNII
A7V27PHC7A
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
MESH
D011803
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
LACTMED
Quinine
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
IUPHAR
2510
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
ChEMBL
CHEMBL170
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
NSC
192949
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
WIKIPEDIA
QUININE
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
SMS_ID
100000078599
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-003-2
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
HSDB
2501
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
RXCUI
9071
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY RxNorm
CAS
130-95-0
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
NCI_THESAURUS
C794
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
DRUG BANK
DB00468
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
MERCK INDEX
m9447
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY Merck Index
EVMPD
SUB15084MIG
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
PUBCHEM
3034034
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID0044280
Created by admin on Fri Dec 15 15:13:35 UTC 2023 , Edited by admin on Fri Dec 15 15:13:35 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
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
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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