Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C20H24N2O2.C6H8O7 |
Molecular Weight | 840.957 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(O)(CC(O)=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.[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=YSFIPRFOHJQXJF-VMJVVOMYSA-N
InChI=1S/2C20H24N2O2.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t2*13-,14-,19-,20+;/m00./s1
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 |
---|---|---|
Quinine-induced alterations of electrically evoked otoacoustic emissions and cochlear potentials in guinea pigs. | 2001 Apr |
|
Cell volume-induced changes in K+ transport across the rat colon. | 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 |
|
The first stereoselective total synthesis of quinine. | 2001 Apr 11 |
|
Role of parabrachial nucleus in submandibular salivary secretion induced by bitter taste stimulation in rats. | 2001 Apr 12 |
|
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 |
|
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 |
|
Large-conductance calcium-activated potassium channels in neonatal rat intracardiac ganglion neurons. | 2001 Feb |
|
Determination of cisapride in pharmaceutical preparations using derivative spectrophotometry. | 2001 Feb |
|
In vitro antiplasmodial activity of 4-phenylcoumarins from Exostema mexicanum. | 2001 Feb |
|
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 |
|
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 |
|
Myosin II-dependent cylindrical protrusions induced by quinine in Dictyostelium: antagonizing effects of actin polymerization at the leading edge. | 2001 Jun |
|
The effect of laser assisted uvulopalatoplasty on the sense of smell and taste. | 2001 Jun |
|
Influence of quinine on catecholamine release evoked by cholinergic stimulation and membrane depolarization from the rat adrenal gland. | 2001 Jun |
|
Therapeutic efficacy of sulphadoxine/pyrimethamine and susceptibility in vitro of P. falciparum isolates to sulphadoxine-pyremethamine and other antimalarial drugs in Malawian children. | 2001 Jun |
|
A comparison of brain, core and skin temperature in children with complicated and uncomplicated malaria. | 2001 Jun |
|
Nocturnal leg cramps. Clinically mysterious and painful--but manageable. | 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 |
|
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 |
|
Genomic and functional characteristics of novel human pancreatic 2P domain K(+) channels. | 2001 Mar 23 |
|
[Severe malaria]. | 2001 Mar 31 |
|
Exchange transfusion for severe malaria. | 2001 Mar-Apr |
|
Oral quinine pharmacokinetics and dietary salt intake. | 2001 May |
|
Changes in taste intensity perception following anterior temporal lobe removal in humans. | 2001 May |
|
Interaction of gustatory and lingual somatosensory perceptions at the cortical level in the human: a functional magnetic resonance imaging study. | 2001 May |
|
Treatment alternatives for nocturnal leg cramps. | 2001 May 21 |
|
Evaluation of the contribution to enantioselectivity of quinine and quinidine scaffolds in chemically and physically mixed chiral selectors. | 2001 May 5 |
|
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 |
|
A clinical and pharmacokinetic trial of six doses of artemether-lumefantrine for multidrug-resistant Plasmodium falciparum malaria in Thailand. | 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 |
|
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 |
|
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 |
|
Optochin resistance in Streptococcus pneumoniae: mechanism, significance, and clinical implications. | 2001 Sep 1 |
|
HPLC of basic drugs on microparticulate strong cation-exchange materials - a review. | 2001 Sep 15 |
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)
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
CFR |
21 CFR 310.547
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
71586768
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
PRIMARY | |||
|
DBSALT002255
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
PRIMARY | |||
|
L8D5LFU229
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
PRIMARY | |||
|
100000078601
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
PRIMARY | |||
|
SUB15089MIG
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
PRIMARY | |||
|
752-72-7
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
PRIMARY | |||
|
DTXSID10226178
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
PRIMARY | |||
|
212-037-1
Created by
admin on Fri Dec 15 15:13:57 GMT 2023 , Edited by admin on Fri Dec 15 15:13:57 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD