Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H24N2O2.C6H12O7 |
| Molecular Weight | 520.572 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.[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=XHKUDCCTVQUHJQ-BILMMMPYSA-N
InChI=1S/C20H24N2O2.C6H12O7/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;7-1-2(8)3(9)4(10)5(11)6(12)13/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2-5,7-11H,1H2,(H,12,13)/t13-,14-,19-,20+;2-,3-,4+,5-/m01/s1
| Molecular Formula | C20H24N2O2 |
| Molecular Weight | 324.4168 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C6H12O7 |
| Molecular Weight | 196.1553 |
| 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
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 |
|
| 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 |
|
| Simultaneous determination of quinine and four metabolites in plasma and urine by high-performance liquid chromatography. | 2001 Apr 15 |
|
| Resurgence of blackwater fever in long-term European expatriates in Africa: report of 21 cases and review. | 2001 Apr 15 |
|
| Severe babesiosis in Long Island: review of 34 cases and their complications. | 2001 Apr 15 |
|
| [Plasmodium vivax: therapy update]. | 2001 Apr 21 |
|
| Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate. | 2001 Apr 27 |
|
| Role of quinine-sensitive ion channels in volume regulation in boar and bull spermatozoa. | 2001 Aug |
|
| Large-conductance calcium-activated potassium channels in neonatal rat intracardiac ganglion neurons. | 2001 Feb |
|
| Reduction of saltiness and bitterness after a chlorhexidine rinse. | 2001 Feb |
|
| Pontine gustatory activity is altered by electrical stimulation in the central nucleus of the amygdala. | 2001 Feb |
|
| Stereocontrolled conversion of quinine into 10(R),11-dihydroxydihydroquinine via the sharpless osmylation process. | 2001 Feb 23 |
|
| Taste receptor cells that discriminate between bitter stimuli. | 2001 Feb 23 |
|
| Babesiosis. | 2001 Jan |
|
| Redox systems as conduits for antimalarial compounds. | 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 |
|
| [Fulminant course of falciparum malaria]. | 2001 Jan 26 |
|
| Evaluation under field conditions of the colourimetric DELI-microtest for the assessment of Plasmodium falciparum drug resistance. | 2001 Jan-Feb |
|
| [Effect of antibodies against S100 proteins on neural plasticity in sensitized and naive snails]. | 2001 Jan-Feb |
|
| Changing epidemiological and clinical aspects of imported malaria in Belgium. | 2001 Jan-Feb |
|
| 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 |
|
| A comparison of brain, core and skin temperature in children with complicated and uncomplicated malaria. | 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 |
|
| [Treatment of acute malaria with quinine in a non-immunized patient: rationale for a 7-day regimen]. | 2001 Mar 17 |
|
| 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 |
|
| Exchange transfusion for severe malaria. | 2001 Mar-Apr |
|
| Oral quinine pharmacokinetics and dietary salt intake. | 2001 May |
|
| Evaluation of the contribution to enantioselectivity of quinine and quinidine scaffolds in chemically and physically mixed chiral selectors. | 2001 May 5 |
|
| Volume-activated trimethylamine oxide efflux in red blood cells of spiny dogfish (Squalus acanthias). | 2001 Sep |
|
| Optochin resistance in Streptococcus pneumoniae: mechanism, significance, and clinical implications. | 2001 Sep 1 |
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 19:08:17 GMT 2023
by
admin
on
Sat Dec 16 19:08:17 GMT 2023
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| Record UNII |
RQ979Q6A3F
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| Record Status |
Validated (UNII)
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| Record Version |
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4325-25-1
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RQ979Q6A3F
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100000115586
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ACTIVE MOIETY |
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