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: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021799s024lbl.pdfhttps://onlinelibrary.wiley.com/doi/abs/10.1002/jps.3080010617Curator's Comment: description was created based on several sources, including
http://www.fda.gov/downloads/ForHealthProfessionals/LearningActivities/UCM317816.pdf
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021799s024lbl.pdfhttps://onlinelibrary.wiley.com/doi/abs/10.1002/jps.3080010617
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
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 |
---|---|---|
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 |
|
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 |
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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 |
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The first stereoselective total synthesis of quinine. | 2001 Apr 11 |
|
[Plasmodium vivax: therapy update]. | 2001 Apr 21 |
|
Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate. | 2001 Apr 27 |
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In vitro antiplasmodial activity of 4-phenylcoumarins from Exostema mexicanum. | 2001 Feb |
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Delayed quinine toxicity mimicking open angle glaucoma. | 2001 Feb |
|
BK channels in human glioma cells. | 2001 Feb |
|
Adrenocorticotropic hormone activates an outward current in cultured mouse peritoneal macrophages. | 2001 Feb 15 |
|
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 |
|
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 |
|
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells. | 2001 Jul |
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Sapid solutions and food intake in repeated dehydration and rehydration periods in rats. | 2001 Jul |
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Distribution of gustatory sensitivities in rat taste cells: whole-cell responses to apical chemical stimulation. | 2001 Jul 1 |
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Polyvinyl chloride-based membranes for flow injection analysis of quinine in beverages. | 2001 Jul-Aug |
|
Influence of quinine on catecholamine release evoked by cholinergic stimulation and membrane depolarization from the rat adrenal gland. | 2001 Jun |
|
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada. | 2001 Jun 12 |
|
[Photodermatosis induced by hydroxychloroquine: 4 cases]. | 2001 Jun-Jul |
|
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy. | 2001 Mar |
|
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels. | 2001 Mar 23 |
|
[Severe malaria]. | 2001 Mar 31 |
|
Hyperpolarizing shift by quinine in the steady-state inactivation curve of delayed rectifier-type potassium current in bullfrog sympathetic neurons. | 2001 Mar 9 |
|
Exchange transfusion for severe malaria. | 2001 Mar-Apr |
|
Oral quinine pharmacokinetics and dietary salt intake. | 2001 May |
|
Effect of compound sequence on bitterness enhancement. | 2001 May |
|
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 |
|
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
by
admin
on
Edited
Fri Dec 16 16:32:52 UTC 2022
by
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on
Fri Dec 16 16:32:52 UTC 2022
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Record UNII |
A7V27PHC7A
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Record Status |
Validated (UNII)
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Record Version |
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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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15854
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137041
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52251
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A7V27PHC7A
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4523
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A7V27PHC7A
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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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205-003-2
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2501
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9071
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PRIMARY | RxNorm | ||
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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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SUB15084MIG
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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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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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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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TRANSPORTER -> INHIBITOR | |||
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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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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 -> SUBSTRATE | |||
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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 |
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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