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

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O2.ClH.2H2O
Molecular Weight 396.908
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE HYDROCHLORIDE

SMILES

O.O.Cl.[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=MPQKYZPYCSTMEI-FLZPLBAKSA-N
InChI=1S/C20H24N2O2.ClH.2H2O/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;1H;2*1H2/t13-,14-,19-,20+;;;/m0.../s1

HIDE SMILES / InChI

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 ClH
Molecular Weight 36.461
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
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
Two procedures establishing preference for oral cocaine and lidocaine solutions which do not use an associative history with a reinforcer.
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
Resurgence of blackwater fever in long-term European expatriates in Africa: report of 21 cases and review.
2001 Apr 15
Ferrocene-chloroquine analogues as antimalarial agents: in vitro activity of ferrochloroquine against 103 Gabonese isolates of Plasmodium falciparum.
2001 Aug
Determination of cisapride in pharmaceutical preparations using derivative spectrophotometry.
2001 Feb
Reduction of saltiness and bitterness after a chlorhexidine rinse.
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
Taste receptor cells that discriminate between bitter stimuli.
2001 Feb 23
Ethanol perception and ingestion.
2001 Jan
Comparative expression of hedonic impact: affective reactions to taste by human infants and other primates.
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
Effect of extracellular Ca2+ on the quinine-activated current of bullfrog taste receptor cells.
2001 Jan 15
[Fulminant course of falciparum malaria].
2001 Jan 26
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
Simultaneous determination of etoposide and its catechol metabolite in the plasma of pediatric patients by liquid chromatography/tandem mass spectrometry.
2001 Jul
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
Capillary electrophoretic separation, immunochemical recognition and analysis of the diastereomers quinine and quinidine and two quinidine metabolites in body fluids.
2001 Mar
Hyperpolarizing shift by quinine in the steady-state inactivation curve of delayed rectifier-type potassium current in bullfrog sympathetic neurons.
2001 Mar 9
Evaluation of the contribution to enantioselectivity of quinine and quinidine scaffolds in chemically and physically mixed chiral selectors.
2001 May 5
Effects of the ion-channel blocker quinine on human sperm volume, kinematics and mucus penetration, and the involvement of potassium channels.
2001 Sep
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
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 15:13:31 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:31 GMT 2023
Record UNII
711S8Y0T33
Record Status Validated (UNII)
Record Version
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Name Type Language
QUININE HYDROCHLORIDE
EP   FCC   MART.   WHO-IP  
Common Name English
QUININE HYDROCHLORIDE DIHYDRATE
MART.   MI   USP-RS   WHO-DD  
Common Name English
QUININE HYDROCHLORIDE [FCC]
Common Name English
QUININI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
(8.ALPHA.,9R)-6'-METHOXYCINCHONAN-9-OL HYDROCHLORIDE DIHYDRATE
Common Name English
QUININE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
QUININE MONOHYDROCHLORIDE
Common Name English
QUININE HYDROCHLORIDE DIHYDRATE [USP-RS]
Common Name English
CHININUM MURIATICUM
HPUS  
Common Name English
FEMA NO. 2976, DIHYDRATE-
Code English
QUININE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
QUININE HCL
Common Name English
QUININE HYDROCHLORIDE DIHYDRATE [MART.]
Common Name English
QUININE HYDROCHLORIDE [MART.]
Common Name English
QUININE MONOHYDROCHLORIDE DIHYDRATE
Common Name English
QUININE HYDROCHLORIDE [WHO-IP]
Common Name English
QUININE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
QUININE HYDROCHLORIDE DIHYDRATE [MI]
Common Name English
QUININE MONOHYDROCHLORIDE DIHYRATE
Common Name English
Quinine hydrochloride dihydrate [WHO-DD]
Common Name English
CHININUM MURIATICUM [HPUS]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION QUININE HYDROCHLORIDE
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
CFR 21 CFR 310.547
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
Code System Code Type Description
RXCUI
9074
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY RxNorm
EVMPD
SUB15093MIG
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID2047694
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
MERCK INDEX
m9447
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY Merck Index
DRUG BANK
DBSALT001044
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
CAS
6119-47-7
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
PUBCHEM
16211283
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
FDA UNII
711S8Y0T33
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
NCI_THESAURUS
C75269
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL170
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
RS_ITEM_NUM
1596807
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
DAILYMED
711S8Y0T33
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
QUININE HYDROCHLORIDE
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY Description: Silky, colourless crystals, often grouped in clusters; odourless. Solubility: Soluble in water; freely soluble in ethanol (~750 g/l) TS; very slightly soluble in ether R. Category: Antimalarial. Storage: Quinine hydrochloride should be kept in a well-closed container, protected from light. Additional information. Quinine hydrochloride has a very bitter taste. Definition: Quinine hydrochloride contains not less than 98.5% and not more than 101.0% of total alkaloids, calculated as C20H24N2O2,HCl and with reference to the dried substance.
SMS_ID
100000090455
Created by admin on Fri Dec 15 15:13:31 GMT 2023 , Edited by admin on Fri Dec 15 15:13:31 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY