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

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C20H24N2O2.H2O4S
Molecular Weight 746.912
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE SULFATE ANHYDROUS

SMILES

OS(O)(=O)=O.[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C3=C4C=C(OC)C=CC4=NC=C3.[H][C@]5(C[C@@H]6CC[N@]5C[C@@H]6C=C)[C@H](O)C7=C8C=C(OC)C=CC8=NC=C7

InChI

InChIKey=RONWGALEIBILOG-VMJVVOMYSA-N
InChI=1S/2C20H24N2O2.H2O4S/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;1-5(2,3)4/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4)/t2*13-,14-,19-,20+;/m00./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

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
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
The effect of artesunate combined with standard antimalarials against chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum in vitro.
1999 Jul-Aug
Olfactory learning induces differential long-lasting changes in rat central olfactory pathways.
2001
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
Severe babesiosis in Long Island: review of 34 cases and their complications.
2001 Apr 15
Quinine-induced thrombocytopenia in a 64-year-old man who consumed tonic water to relieve nocturnal leg cramps.
2001 Aug
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
In vitro antiplasmodial activity of 4-phenylcoumarins from Exostema mexicanum.
2001 Feb
BK channels in human glioma cells.
2001 Feb
Infusional CHOP chemotherapy (CVAD) with or without chemosensitizers offers no advantage over standard CHOP therapy in the treatment of lymphoma: a Southwest Oncology Group Study.
2001 Feb 1
Stereocontrolled conversion of quinine into 10(R),11-dihydroxydihydroquinine via the sharpless osmylation process.
2001 Feb 23
Ethanol perception and ingestion.
2001 Jan
Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods.
2001 Jan
Babesiosis.
2001 Jan
[Fulminant course of falciparum malaria].
2001 Jan 26
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
Changing epidemiological and clinical aspects of imported malaria in Belgium.
2001 Jan-Feb
Taste responses in sons of male alcoholics.
2001 Jan-Feb
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
Lateral parabrachial nucleus lesions in the rat: neophobia and conditioned taste aversion.
2001 Jun
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada.
2001 Jun 12
Mechanisms by which intracellular calcium induces susceptibility to secretory phospholipase A2 in human erythrocytes.
2001 Jun 22
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy.
2001 Mar
The treatment of babesiosis.
2001 Mar 8
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
Chemistry. Synthetic lessons from quinine.
2001 May 24
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
Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1.
2001 Sep
Septic shock due to babesiosis.
2001 Sep 1
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 Dec 16 02:05:41 GMT 2023
Edited
by admin
on Sat Dec 16 02:05:41 GMT 2023
Record UNII
M4XCR57IWG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUININE SULFATE ANHYDROUS
Common Name English
QUININE SULFATE ANHYDROUS [MI]
Common Name English
NSC-5362
Code English
QUININE SULFATE (2:1)
Common Name English
QUININE, SULFATE (2:1) (SALT)
Common Name English
ANHYDROUS QUININE SULFATE [MART.]
Common Name English
ANHYDROUS QUININE SULFATE
MART.  
Common Name English
CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9R)-, SULFATE (2:1)
Common Name English
Quinine sulfate [WHO-DD]
Common Name English
CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9R)-, SULFATE (2:1) (SALT)
Common Name English
QUININE HEMISULFATE ANHYDROUS
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.546
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
Code System Code Type Description
NSC
5362
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
PRIMARY
FDA UNII
M4XCR57IWG
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
PRIMARY
MERCK INDEX
m9447
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-359-2
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
PRIMARY
CAS
804-63-7
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID50859000
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
PRIMARY
CHEBI
52250
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
PRIMARY
PUBCHEM
16051948
Created by admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY