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

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O2.2ClH
Molecular Weight 397.339
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE DIHYDROCHLORIDE

SMILES

Cl.Cl.[H][C@]1(C[C@@H]2CCN1C[C@@H]2C=C)[C@H](O)C3=C4C=C(OC)C=CC4=NC=C3

InChI

InChIKey=NNKXWRRDHYTHFP-HZQSTTLBSA-N
InChI=1S/C20H24N2O2.2ClH/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;2*1H/t13-,14-,19-,20+;;/m0../s1

HIDE SMILES / InChI

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
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
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
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
The applicability of rat and human liver slices to the study of mechanisms of hepatic drug uptake.
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
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
Myosin II-dependent cylindrical protrusions induced by quinine in Dictyostelium: antagonizing effects of actin polymerization at the leading edge.
2001 Jun
Lateral parabrachial nucleus lesions in the rat: neophobia and conditioned taste aversion.
2001 Jun
The effect of laser assisted uvulopalatoplasty on the sense of smell and taste.
2001 Jun
Influence of quinine on catecholamine release evoked by cholinergic stimulation and membrane depolarization from the rat adrenal gland.
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
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
Effects of hydroxypyridinone iron chelators in combination with antimalarial drugs on the in vitro growth of Plasmodium falciparum.
2001 Mar
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy.
2001 Mar
[Treatment of acute malaria with quinine in a non-immunized patient: rationale for a 7-day regimen].
2001 Mar 17
[Severe malaria].
2001 Mar 31
Exchange transfusion for severe malaria.
2001 Mar-Apr
Oral quinine pharmacokinetics and dietary salt intake.
2001 May
Changes in taste intensity perception following anterior temporal lobe removal in humans.
2001 May
Effect of compound sequence on bitterness enhancement.
2001 May
Interaction of gustatory and lingual somatosensory perceptions at the cortical level in the human: a functional magnetic resonance imaging study.
2001 May
Chemistry. Synthetic lessons from quinine.
2001 May 24
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
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
Antimalarial activity of azithromycin, artemisinin and dihydroartemisinin in fresh isolates of Plasmodium falciparum in Thailand.
2001 Sep 1
HPLC of basic drugs on microparticulate strong cation-exchange materials - a review.
2001 Sep 15
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 15:03:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:39 GMT 2023
Record UNII
8C3EMH7D9X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUININE DIHYDROCHLORIDE
MART.   MI   WHO-DD   WHO-IP  
Common Name English
NEUTRAL QUININE HYDROCHLORIDE
Common Name English
QUININE DIHYDROCHLORIDE [MART.]
Common Name English
QUININE BIMURIATE
Common Name English
ACID QUININE HYDROCHLORIDE
Common Name English
QUININE DIHYDROCHLORIDE [WHO-IP]
Common Name English
CINCHONAN-9-OL, 6'-METHOXY-, HYDROCHLORIDE (1:2), (8.ALPHA.,9R)-
Common Name English
QUININI DIHYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
QUININE DIHYDROCHLORIDE [MI]
Common Name English
Quinine dihydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.547
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
Code System Code Type Description
CAS
60-93-5
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY
ChEMBL
CHEMBL170
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY
PUBCHEM
91429
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY
FDA UNII
8C3EMH7D9X
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY
EVMPD
SUB125762
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY
RXCUI
388472
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-493-4
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY
MERCK INDEX
m9447
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID00975421
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
QUININE DIHYDROCHLORIDE
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY Description: A white or almost white, crystalline powder; odourless.Solubility: Very soluble in water; soluble in ethanol (~750 g/l) TS; practically insoluble in ether R.Category: Antimalarial drug.Storage: Quinine dihydrochloride should be kept in a well-closed container, protected from light.Additional information: Quinine dihydrochloride turns yellow on exposure to light. Even in the absence of light, it is graduallydegraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures.Definition: Quinine dihydrochloride contains not less than 99.0% and not more than 101.0% of total alkaloids, calculated as C20H24N2O2,2HCl and with reference to the dried substance.
SMS_ID
100000146246
Created by admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE