Details
| Stereochemistry | EPIMERIC |
| Molecular Formula | C20H24N2O2.C3H6O3 |
| Molecular Weight | 414.4947 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(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=ZIDGEHZBXVXPFQ-DSXUQNDKSA-N
InChI=1S/C20H24N2O2.C3H6O3/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;1-2(4)3(5)6/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2,4H,1H3,(H,5,6)/t13-,14-,19-,20+;/m0./s1
| Molecular Formula | C3H6O3 |
| Molecular Weight | 90.0779 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| 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: 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 |
|---|---|---|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| The applicability of rat and human liver slices to the study of mechanisms of hepatic drug uptake. | 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 |
|
| Simultaneous determination of etoposide and its catechol metabolite in the plasma of pediatric patients by liquid chromatography/tandem mass spectrometry. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Transfusion-transmitted babesiosis in Ontario: first reported case in Canada. | 2001 Jun 12 |
|
| Dynamic and multimodal responses of gustatory cortical neurons in awake rats. | 2001 Jun 15 |
|
| [Photodermatosis induced by hydroxychloroquine: 4 cases]. | 2001 Jun-Jul |
|
| Effects of hydroxypyridinone iron chelators in combination with antimalarial drugs on the in vitro growth of Plasmodium falciparum. | 2001 Mar |
|
| Oral quinine pharmacokinetics and dietary salt intake. | 2001 May |
|
| Changes in taste intensity perception following anterior temporal lobe removal in humans. | 2001 May |
|
| Effect of compound sequence on bitterness enhancement. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 09:24:36 GMT 2023
by
admin
on
Sat Dec 16 09:24:36 GMT 2023
|
| Record UNII |
7J99Y4IZE5
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
23617236
Created by
admin on Sat Dec 16 09:24:36 GMT 2023 , Edited by admin on Sat Dec 16 09:24:36 GMT 2023
|
PRIMARY | |||
|
749-49-5
Created by
admin on Sat Dec 16 09:24:36 GMT 2023 , Edited by admin on Sat Dec 16 09:24:36 GMT 2023
|
PRIMARY | |||
|
DTXSID20225874
Created by
admin on Sat Dec 16 09:24:36 GMT 2023 , Edited by admin on Sat Dec 16 09:24:36 GMT 2023
|
PRIMARY | |||
|
7J99Y4IZE5
Created by
admin on Sat Dec 16 09:24:36 GMT 2023 , Edited by admin on Sat Dec 16 09:24:36 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
