Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H24N2O2.2BrH.3H2O |
| Molecular Weight | 540.286 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.Br.Br.[H][C@]1(C[C@@H]2CCN1C[C@@H]2C=C)[C@H](O)C3=C4C=C(OC)C=CC4=NC=C3
InChI
InChIKey=HQWBWOCBZJFIJL-YHKMUBIUSA-N
InChI=1S/C20H24N2O2.2BrH.3H2O/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;3*1H2/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 |
| Molecular Formula | BrH |
| Molecular Weight | 80.912 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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
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 |
|---|---|---|
| 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 |
|
| 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 |
|
| Resurgence of blackwater fever in long-term European expatriates in Africa: report of 21 cases and review. | 2001 Apr 15 |
|
| Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate. | 2001 Apr 27 |
|
| 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 |
|
| Reduction of saltiness and bitterness after a chlorhexidine rinse. | 2001 Feb |
|
| Delayed quinine toxicity mimicking open angle glaucoma. | 2001 Feb |
|
| Computer-simulation studies on roles of potassium currents in neurotransmission of the auditory nerve. | 2001 Feb |
|
| Activation of ion-conducting pathways in the inner mitochondrial membrane - an unrecognized activity of fatty acid? | 2001 Feb 23 |
|
| Taste receptor cells that discriminate between bitter stimuli. | 2001 Feb 23 |
|
| Ethanol perception and ingestion. | 2001 Jan |
|
| Uptake properties of lamivudine (3TC) by a continuous renal epithelial cell line. | 2001 Jan |
|
| Declining chloroquine resistance of Plasmodium falciparum in Lambaréné, Gabon from 1992 to 1998. | 2001 Jan 15 |
|
| 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 |
|
| The applicability of rat and human liver slices to the study of mechanisms of hepatic drug uptake. | 2001 Jan-Feb |
|
| Evaluation under field conditions of the colourimetric DELI-microtest for the assessment of Plasmodium falciparum drug resistance. | 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 |
|
| Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells. | 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 |
|
| 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 |
|
| A comparison of brain, core and skin temperature in children with complicated and uncomplicated malaria. | 2001 Jun |
|
| 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 |
|
| Effects of hydroxypyridinone iron chelators in combination with antimalarial drugs on the in vitro growth of Plasmodium falciparum. | 2001 Mar |
|
| Capillary electrophoretic separation, immunochemical recognition and analysis of the diastereomers quinine and quinidine and two quinidine metabolites in body fluids. | 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 |
|
| The treatment of babesiosis. | 2001 Mar 8 |
|
| Hyperpolarizing shift by quinine in the steady-state inactivation curve of delayed rectifier-type potassium current in bullfrog sympathetic neurons. | 2001 Mar 9 |
|
| Oral quinine pharmacokinetics and dietary salt intake. | 2001 May |
|
| Treatment alternatives for nocturnal leg cramps. | 2001 May 21 |
|
| 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 |
|
| Effects of the ion-channel blocker quinine on human sperm volume, kinematics and mucus penetration, and the involvement of potassium channels. | 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 |
Sample Use Guides
in adults: 648 mg (two capsules) every 8 hours for 7 days
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:03:43 GMT 2023
by
admin
on
Sat Dec 16 02:03:43 GMT 2023
|
| Record UNII |
D7WN8V134E
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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71586869
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6119-41-1
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D7WN8V134E
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DTXSID40976699
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ANHYDROUS->SOLVATE |
