Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H24N2O2.2ClH |
Molecular Weight | 397.339 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.[H][C@]1(C[C@@H]2CCN1C[C@@H]2C=C)[C@H](O)C3=C4C=C(OC)C=CC4=NC=C3
InChI
InChIKey=NNKXWRRDHYTHFP-HZQSTTLBSA-N
InChI=1S/C20H24N2O2.2ClH/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/t13-,14-,19-,20+;;/m0../s1
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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
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 Date1.12380477E12 |
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 |
|
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 |
|
Use of the DELI-microtest to determine the drug sensitivity of Plasmodium falciparum in Burkina Faso. | 2001 Apr |
|
Quinine-induced thrombocytopenia in a 64-year-old man who consumed tonic water to relieve nocturnal leg cramps. | 2001 Aug |
|
Ferrocene-chloroquine analogues as antimalarial agents: in vitro activity of ferrochloroquine against 103 Gabonese isolates of Plasmodium falciparum. | 2001 Aug |
|
Activation of ion-conducting pathways in the inner mitochondrial membrane - an unrecognized activity of fatty acid? | 2001 Feb 23 |
|
Uptake properties of lamivudine (3TC) by a continuous renal epithelial cell line. | 2001 Jan |
|
Comparative expression of hedonic impact: affective reactions to taste by human infants and other primates. | 2001 Jan |
|
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 |
|
Nocturnal leg cramps. Clinically mysterious and painful--but manageable. | 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 |
|
[Severe malaria]. | 2001 Mar 31 |
|
Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family. | 2001 Mar 9 |
|
Effect of compound sequence on bitterness enhancement. | 2001 May |
|
Molecular cloning and characterization of a novel (Na+,K+)/H+ exchanger localized to the trans-Golgi network. | 2001 May 18 |
|
Chemistry. Synthetic lessons from quinine. | 2001 May 24 |
|
A clinical and pharmacokinetic trial of six doses of artemether-lumefantrine for multidrug-resistant Plasmodium falciparum malaria in Thailand. | 2001 May-Jun |
|
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 |
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
Fri Dec 15 15:03:39 UTC 2023
by
admin
on
Fri Dec 15 15:03:39 UTC 2023
|
Record UNII |
8C3EMH7D9X
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | 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 | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
CFR |
21 CFR 310.547
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
60-93-5
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | |||
|
CHEMBL170
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | |||
|
91429
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | |||
|
8C3EMH7D9X
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | |||
|
SUB125762
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | |||
|
388472
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | RxNorm | ||
|
200-493-4
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | |||
|
m9447
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | Merck Index | ||
|
DTXSID00975421
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | |||
|
QUININE DIHYDROCHLORIDE
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY | Description: A white or almost white, crystalline powder; odourless.Solubility: Very soluble in water; soluble in ethanol (~750 g/l) TS; practically insoluble in ether R.Category: Antimalarial drug.Storage: Quinine dihydrochloride should be kept in a well-closed container, protected from light.Additional information: Quinine dihydrochloride turns yellow on exposure to light. Even in the absence of light, it is graduallydegraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures.Definition: Quinine dihydrochloride contains not less than 99.0% and not more than 101.0% of total alkaloids, calculated as C20H24N2O2,2HCl and with reference to the dried substance. | ||
|
100000146246
Created by
admin on Fri Dec 15 15:03:40 UTC 2023 , Edited by admin on Fri Dec 15 15:03:40 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |