Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C20H24N2O2.H2O4S |
Molecular Weight | 746.912 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=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.[H][C@]5(C[C@@H]6CC[N@]5C[C@@H]6C=C)[C@H](O)C7=C8C=C(OC)C=CC8=NC=C7
InChI
InChIKey=RONWGALEIBILOG-VMJVVOMYSA-N
InChI=1S/2C20H24N2O2.H2O4S/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;1-5(2,3)4/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4)/t2*13-,14-,19-,20+;/m00./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 | H2O4S |
Molecular Weight | 98.078 |
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
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 Date2005 |
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 |
|
Olfactory learning induces differential long-lasting changes in rat central olfactory pathways. | 2001 |
|
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 |
|
Severe babesiosis in Long Island: review of 34 cases and their complications. | 2001 Apr 15 |
|
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 |
|
Role of quinine-sensitive ion channels in volume regulation in boar and bull spermatozoa. | 2001 Aug |
|
In vitro antiplasmodial activity of 4-phenylcoumarins from Exostema mexicanum. | 2001 Feb |
|
BK channels in human glioma cells. | 2001 Feb |
|
Infusional CHOP chemotherapy (CVAD) with or without chemosensitizers offers no advantage over standard CHOP therapy in the treatment of lymphoma: a Southwest Oncology Group Study. | 2001 Feb 1 |
|
Stereocontrolled conversion of quinine into 10(R),11-dihydroxydihydroquinine via the sharpless osmylation process. | 2001 Feb 23 |
|
Ethanol perception and ingestion. | 2001 Jan |
|
Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods. | 2001 Jan |
|
Babesiosis. | 2001 Jan |
|
[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 |
|
[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 |
|
Distribution of gustatory sensitivities in rat taste cells: whole-cell responses to apical chemical stimulation. | 2001 Jul 1 |
|
A comparison of the in vivo kinetics of Plasmodium falciparum ring-infected erythrocyte surface antigen-positive and -negative erythrocytes. | 2001 Jul 15 |
|
Polyvinyl chloride-based membranes for flow injection analysis of quinine in beverages. | 2001 Jul-Aug |
|
Lateral parabrachial nucleus lesions in the rat: neophobia and conditioned taste aversion. | 2001 Jun |
|
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada. | 2001 Jun 12 |
|
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 |
|
The treatment of babesiosis. | 2001 Mar 8 |
|
Oral quinine pharmacokinetics and dietary salt intake. | 2001 May |
|
Changes in taste intensity perception following anterior temporal lobe removal in humans. | 2001 May |
|
Treatment alternatives for nocturnal leg cramps. | 2001 May 21 |
|
Chemistry. Synthetic lessons from quinine. | 2001 May 24 |
|
Is multiple sclerosis caused by a silent infection with malarial parasites? A historico-epidemiological approach: part II. | 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 |
|
Septic shock due to babesiosis. | 2001 Sep 1 |
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
Sat Dec 16 02:05:41 GMT 2023
by
admin
on
Sat Dec 16 02:05:41 GMT 2023
|
Record UNII |
M4XCR57IWG
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
CFR |
21 CFR 310.546
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
5362
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
PRIMARY | |||
|
M4XCR57IWG
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
PRIMARY | |||
|
m9447
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
PRIMARY | |||
|
212-359-2
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
PRIMARY | |||
|
804-63-7
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
PRIMARY | |||
|
DTXSID50859000
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
PRIMARY | |||
|
52250
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
PRIMARY | |||
|
16051948
Created by
admin on Sat Dec 16 02:05:41 GMT 2023 , Edited by admin on Sat Dec 16 02:05:41 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SOLVATE->ANHYDROUS |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |