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

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 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 H2O
Molecular Weight 18.0153
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

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

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
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
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
Use of the DELI-microtest to determine the drug sensitivity of Plasmodium falciparum in Burkina Faso.
2001 Apr
The first stereoselective total synthesis of quinine.
2001 Apr 11
Simultaneous determination of quinine and four metabolites in plasma and urine by high-performance liquid chromatography.
2001 Apr 15
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
Determination of cisapride in pharmaceutical preparations using derivative spectrophotometry.
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
Adrenocorticotropic hormone activates an outward current in cultured mouse peritoneal macrophages.
2001 Feb 15
Activation of ion-conducting pathways in the inner mitochondrial membrane - an unrecognized activity of fatty acid?
2001 Feb 23
Uptake properties of lamivudine (3TC) by a continuous renal epithelial cell line.
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
Comparative expression of hedonic impact: affective reactions to taste by human infants and other primates.
2001 Jan
Babesiosis.
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
Declining chloroquine resistance of Plasmodium falciparum in Lambaréné, Gabon from 1992 to 1998.
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
Changing epidemiological and clinical aspects of imported malaria in Belgium.
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
Covariation in individuals' sensitivities to bitter compounds: evidence supporting multiple receptor/transduction mechanisms.
2001 Jul
Apparent drug failure following artesunate treatment of Plasmodium falciparum malaria in Freetown, Sierra Leone: four case reports.
2001 Jul
Sapid solutions and food intake in repeated dehydration and rehydration periods in rats.
2001 Jul
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
The effect of laser assisted uvulopalatoplasty on the sense of smell and taste.
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
Dynamic and multimodal responses of gustatory cortical neurons in awake rats.
2001 Jun 15
[Photodermatosis induced by hydroxychloroquine: 4 cases].
2001 Jun-Jul
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
[Severe malaria].
2001 Mar 31
Exchange transfusion for severe malaria.
2001 Mar-Apr
Oral quinine pharmacokinetics and dietary salt intake.
2001 May
Interaction of gustatory and lingual somatosensory perceptions at the cortical level in the human: a functional magnetic resonance imaging study.
2001 May
Molecular cloning and characterization of a novel (Na+,K+)/H+ exchanger localized to the trans-Golgi network.
2001 May 18
Chemistry. Synthetic lessons from quinine.
2001 May 24
Evaluation of the contribution to enantioselectivity of quinine and quinidine scaffolds in chemically and physically mixed chiral selectors.
2001 May 5
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
Effects of the ion-channel blocker quinine on human sperm volume, kinematics and mucus penetration, and the involvement of potassium channels.
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 Wed Jul 05 22:44:29 UTC 2023
Edited
by admin
on Wed Jul 05 22:44:29 UTC 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 Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID00977400
Created by admin on Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 2023
PRIMARY
CAS
6183-68-2
Created by admin on Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 2023
PRIMARY
SMS_ID
100000137679
Created by admin on Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 2023
PRIMARY
MERCK INDEX
M9447
Created by admin on Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 2023
PRIMARY Merck Index
FDA UNII
GNS01V2R3N
Created by admin on Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 2023
PRIMARY
PUBCHEM
67123961
Created by admin on Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 2023
PRIMARY
EVMPD
SUB76232
Created by admin on Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
QUININE BISULFATE HEPTAHYDRATE
Created by admin on Wed Jul 05 22:44:29 UTC 2023 , Edited by admin on Wed Jul 05 22:44:29 UTC 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