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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O2.7H2O.H2O4S
Molecular Weight 548.602
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE BISULFATE HEPTAHYDRATE

SMILES

O.O.O.O.O.O.O.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

InChI

InChIKey=MMZACAMEMISONC-RYXXBYBMSA-N
InChI=1S/C20H24N2O2.H2O4S.7H2O/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;1-5(2,3)4;;;;;;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4);7*1H2/t13-,14-,19-,20+;;;;;;;;/m0......../s1

HIDE SMILES / InChI

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

Molecular Formula H2O
Molecular Weight 18.0153
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

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
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
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
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.
2001 Apr
[Plasmodium vivax: therapy update].
2001 Apr 21
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
Role of quinine-sensitive ion channels in volume regulation in boar and bull spermatozoa.
2001 Aug
Determination of cisapride in pharmaceutical preparations using derivative spectrophotometry.
2001 Feb
BK channels in human glioma cells.
2001 Feb
Taste receptor cells that discriminate between bitter stimuli.
2001 Feb 23
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
Comparative expression of hedonic impact: affective reactions to taste by human infants and other primates.
2001 Jan
Babesiosis.
2001 Jan
Redox systems as conduits for antimalarial compounds.
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
Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates.
2001 Jan 1
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
Evaluation under field conditions of the colourimetric DELI-microtest for the assessment of Plasmodium falciparum drug resistance.
2001 Jan-Feb
Taste responses in sons of male alcoholics.
2001 Jan-Feb
Effectiveness of short-course quinine and single-dose sulfadoxine-pyrimethamine in the treatment of Plasmodium falciparum malaria in Mpumalanga Province, South Africa.
2001 Jul
Apparent drug failure following artesunate treatment of Plasmodium falciparum malaria in Freetown, Sierra Leone: four case reports.
2001 Jul
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells.
2001 Jul
Lateral parabrachial nucleus lesions in the rat: neophobia and conditioned taste aversion.
2001 Jun
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
Nocturnal leg cramps. Clinically mysterious and painful--but manageable.
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
[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
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
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
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
Septic shock due to babesiosis.
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 15:13:01 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:01 GMT 2023
Record UNII
GNS01V2R3N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUININE BISULFATE HEPTAHYDRATE
MI   WHO-DD  
Common Name English
Quinine bisulfate heptahydrate [WHO-DD]
Common Name English
CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9R)-, SULFATE, HYDRATE (1:1:7)
Systematic Name English
QUININI BISULFAS [WHO-IP LATIN]
Common Name English
QUININE BISULFATE [WHO-IP]
Common Name English
QUININE BISULPHATE HEPTAHYDRATE
Common Name English
CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9R)-, SULPHATE (1:1) (SALT), HEPTAHYDRATE
Common Name English
QUININE BISULFATE [MART.]
Common Name English
QUININE BISULFATE HEPTAHYDRATE [MI]
Common Name English
QUININE SULFATE (1:1) (SALT), HEPTAHYDRATE [WHO-IP]
Common Name English
CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9R)-, SULFATE (1:1) (SALT), HEPTAHYDRATE
Common Name English
BIQUINATE
Brand Name English
Classification Tree Code System Code
CFR 21 CFR 310.547
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID00977400
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
PRIMARY
CAS
6183-68-2
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
PRIMARY
SMS_ID
100000137679
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
PRIMARY
MERCK INDEX
m9447
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
PRIMARY Merck Index
FDA UNII
GNS01V2R3N
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
PRIMARY
PUBCHEM
67123961
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
PRIMARY
EVMPD
SUB76232
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
QUININE BISULFATE HEPTAHYDRATE
Created by admin on Fri Dec 15 15:13:01 GMT 2023 , Edited by admin on Fri Dec 15 15:13:01 GMT 2023
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless.Solubility: Freely soluble in water; sparingly soluble in ethanol (~750 g/l) TS.Category: Antimalarial drug.Storage: Quinine bisulfate should be kept in a well-closed container, protected from light.Additional information: Quinine bisulfate effloresces in dry air. Even in the absence of light, it is gradually degraded on exposureto a humid atmosphere, the decomposition being faster at higher temperatures.Definition: Quinine bisulfate contains not less than 98.5% and not more than 101.5% of total alkaloids, calculated as C20H24N2O2,H2SO4 and with reference to the dried substance.
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
Not Specified
IMPURITY -> PARENT
Not Specified
IMPURITY -> PARENT
Not Specified