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

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
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
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
Use of the DELI-microtest to determine the drug sensitivity of Plasmodium falciparum in Burkina Faso.
2001 Apr
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
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
Comparative expression of hedonic impact: affective reactions to taste by human infants and other primates.
2001 Jan
Taste responses in sons of male alcoholics.
2001 Jan-Feb
Sapid solutions and food intake in repeated dehydration and rehydration periods in rats.
2001 Jul
Nocturnal leg cramps. Clinically mysterious and painful--but manageable.
2001 Jun
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
[Severe malaria].
2001 Mar 31
Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family.
2001 Mar 9
Effect of compound sequence on bitterness enhancement.
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
A clinical and pharmacokinetic trial of six doses of artemether-lumefantrine for multidrug-resistant Plasmodium falciparum malaria in Thailand.
2001 May-Jun
Antimalarial activity of azithromycin, artemisinin and dihydroartemisinin in fresh isolates of Plasmodium falciparum in Thailand.
2001 Sep 1
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 Fri Dec 15 15:03:39 UTC 2023
Edited
by admin
on Fri Dec 15 15:03:39 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
Code System Code Type Description
CAS
60-93-5
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL170
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY
PUBCHEM
91429
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY
FDA UNII
8C3EMH7D9X
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY
EVMPD
SUB125762
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY
RXCUI
388472
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-493-4
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY
MERCK INDEX
m9447
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID00975421
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
QUININE DIHYDROCHLORIDE
Created by admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE