Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H24N2O2 |
Molecular Weight | 324.4168 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[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=LOUPRKONTZGTKE-WZBLMQSHSA-N
InChI=1S/C20H24N2O2/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/t13-,14-,19-,20+/m0/s1
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 |
DescriptionSources: https://onlinelibrary.wiley.com/doi/abs/10.1002/jps.3080010617http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021799s024lbl.pdfCurator's Comment: description was created based on several sources, including
http://www.fda.gov/downloads/ForHealthProfessionals/LearningActivities/UCM317816.pdf
Sources: https://onlinelibrary.wiley.com/doi/abs/10.1002/jps.3080010617http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021799s024lbl.pdf
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL613897 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14967191 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | QUALAQUIN Approved Useis a cinchona alkaloid indicated for treatment of uncomplicated Plasmodium falciparum malaria Launch Date1.12380477E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse events |
---|---|---|
5 g single, oral |
unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: M Population Size: 1 Sources: |
Other AEs: Respiratory distress... |
1.8 g single, oral Overdose |
unhealthy, 46 years n = 1 Health Status: unhealthy Age Group: 46 years Sex: F Population Size: 1 Sources: |
Other AEs: Hearing loss... |
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... |
9.75 g single, oral |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: |
Other AEs: Tachycardia... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Respiratory distress | grade 5, 1 patient | 5 g single, oral |
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 |
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 |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
The effect of artesunate combined with standard antimalarials against chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum in vitro. | 1999 Jul-Aug |
|
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 |
|
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 |
|
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 |
|
Babesiosis. | 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 |
|
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 |
|
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 |
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Influence of quinine on catecholamine release evoked by cholinergic stimulation and membrane depolarization from the rat adrenal gland. | 2001 Jun |
|
Mechanisms by which intracellular calcium induces susceptibility to secretory phospholipase A2 in human erythrocytes. | 2001 Jun 22 |
|
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 |
|
Capillary electrophoretic separation, immunochemical recognition and analysis of the diastereomers quinine and quinidine and two quinidine metabolites in body fluids. | 2001 Mar |
|
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels. | 2001 Mar 23 |
|
The treatment of babesiosis. | 2001 Mar 8 |
|
Exchange transfusion for severe malaria. | 2001 Mar-Apr |
|
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 |
|
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 |
|
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 |
|
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 |
Sample Use Guides
in adults: 648 mg (two capsules) every 8 hours for 7 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27089323
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
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Record UNII |
A7V27PHC7A
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Validated (UNII)
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NCI_THESAURUS |
C271
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WHO-ATC |
P01BC01
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CFR |
21 CFR 862.3750
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CFR |
21 CFR 310.546
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DSLD |
2588 (Number of products:3)
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CFR |
21 CFR 172.575
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CFR |
21 CFR 310.547
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NDF-RT |
N0000175482
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WHO-VATC |
QM09AA72
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WHO-ESSENTIAL MEDICINES LIST |
6.5.3.1
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WHO-ATC |
M09AA72
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LIVERTOX |
NBK548596
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D011803
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Quinine
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2510
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CHEMBL170
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192949
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QUININE
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100000078599
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205-003-2
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2501
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9071
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130-95-0
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C794
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DB00468
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M9447
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3034034
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DTXSID0044280
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE LESS ACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE LESS ACTIVE -> PARENT |
Quinine is metabolized almost exclusively via hepatic oxidative cytochrome P450 (CYP) pathways. In vitro studies using human liver microsomes and recombinant P450 enzymes have shown that quinine is metabolized mainly by CYP3A4. Depending on the in vitro experimental conditions, other enzymes, including CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP2E1 were shown to have some role in the metabolism of quinine.
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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