U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O2.CH2O2
Molecular Weight 370.4429
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUININE FORMATE

SMILES

C=C[C@@]1([H])CN2CC[C@@]1([H])C[C@@]2([H])[C@@]([H])(c3ccnc4ccc(cc34)OC)O.C(=O)O

InChI

InChIKey=LKUVXQMSYPYURB-DSXUQNDKSA-N
InChI=1S/C20H24N2O2.CH2O2/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;2-1-3/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;1H,(H,2,3)/t13-,14-,19-,20+;/m0./s1

HIDE SMILES / InChI

Molecular Formula C20H24N2O2
Molecular Weight 324.4175
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula CH2O2
Molecular Weight 46.0254
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: 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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
QUALAQUIN

Approved Use

is a cinchona alkaloid indicated for treatment of uncomplicated Plasmodium falciparum malaria

Launch Date

1123804800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
5 g single, oral
dose: 5 g
route: oral
experiment_type: single
dose_type:
co-adm with
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/2566088
    unhealthy, 17 years
    population: unhealthy
    age: 17 years
    sex: M
    food_status:
    n:
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/2566088
    Other AEs: Respiratory distress...
    Other AEs:
    Respiratory distress (grade 5, 1 patient)

    data_source:
    https://pubmed.ncbi.nlm.nih.gov/2566088
    1.8 g single, oral
    Overdose
    dose: 1.8 g
    route: oral
    experiment_type: single
    dose_type: Overdose
    co-adm with
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/28778932
      unhealthy, 46 years
      population: unhealthy
      age: 46 years
      sex: F
      food_status:
      n:
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/28778932
      Other AEs: Hearing loss...
      Other AEs:
      Hearing loss (1 patient)

      data_source:
      https://pubmed.ncbi.nlm.nih.gov/28778932
      16250 mg single, oral
      Overdose
      dose: 16250 mg
      route: oral
      experiment_type: single
      dose_type: Overdose
      co-adm with
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/8340583
        unhealthy, 49 years
        population: unhealthy
        age: 49 years
        sex: F
        food_status:
        n:
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/8340583
        Other AEs: Cardiotoxicity...
        Other AEs:
        Cardiotoxicity (1 patient)

        data_source:
        https://pubmed.ncbi.nlm.nih.gov/8340583
        9.75 g single, oral
        dose: 9.75 g
        route: oral
        experiment_type: single
        dose_type:
        co-adm with
          data_source:
          https://pubmed.ncbi.nlm.nih.gov/14640479
          unhealthy, adult
          population: unhealthy
          age: adult
          sex: M
          food_status:
          n:
          data_source:
          https://pubmed.ncbi.nlm.nih.gov/14640479
          Other AEs: Tachycardia...
          Other AEs:
          Tachycardia (grade 5)

          data_source:
          https://pubmed.ncbi.nlm.nih.gov/14640479
          AEs

          AEs

          AESignificanceDosePopulation
          Hearing loss 1 pts%
          1.8 g single, oral
          Overdose
          dose: 1.8 g
          route: oral
          experiment_type: single
          dose_type: Overdose
          co-adm with
            data_source:
            https://pubmed.ncbi.nlm.nih.gov/28778932
            unhealthy, 46 years
            population:
            age:
            sex:
            food_status:
            n:
            data_source:
            https://pubmed.ncbi.nlm.nih.gov/28778932
            Cardiotoxicity 1 pts%
            16250 mg single, oral
            Overdose
            dose: 16250 mg
            route: oral
            experiment_type: single
            dose_type: Overdose
            co-adm with
              data_source:
              https://pubmed.ncbi.nlm.nih.gov/8340583
              unhealthy, 49 years
              population:
              age:
              sex:
              food_status:
              n:
              data_source:
              https://pubmed.ncbi.nlm.nih.gov/8340583
              Respiratory distress grade 5,1 pts%
              5 g single, oral
              dose: 5 g
              route: oral
              experiment_type: single
              dose_type:
              co-adm with
                data_source:
                https://pubmed.ncbi.nlm.nih.gov/2566088
                unhealthy, 17 years
                population:
                age:
                sex:
                food_status:
                n:
                data_source:
                https://pubmed.ncbi.nlm.nih.gov/2566088
                Tachycardia grade 5
                9.75 g single, oral
                dose: 9.75 g
                route: oral
                experiment_type: single
                dose_type:
                co-adm with
                  data_source:
                  https://pubmed.ncbi.nlm.nih.gov/14640479
                  unhealthy, adult
                  population:
                  age:
                  sex:
                  food_status:
                  n:
                  data_source:
                  https://pubmed.ncbi.nlm.nih.gov/14640479
                  PubMed

                  PubMed

                  TitleDatePubMed
                  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
                  Patents

                  Sample Use Guides

                  in adults: 648 mg (two capsules) every 8 hours for 7 days
                  Route of Administration: Oral
                  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 Sat Jun 26 08:53:51 UTC 2021
                  Edited
                  by admin
                  on Sat Jun 26 08:53:51 UTC 2021
                  Record UNII
                  F87792011E
                  Record Status Validated (UNII)
                  Record Version
                  • Download
                  Name Type Language
                  QUININE FORMATE
                  WHO-DD  
                  Common Name English
                  QUININE, FORMATE (1:1) (SALT)
                  Common Name English
                  CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9R)-, MONOFORMATE (SALT)
                  Common Name English
                  QUININE FORMATE [WHO-DD]
                  Common Name English
                  QUINOFORM
                  Common Name English
                  Classification Tree Code System Code
                  CFR 21 CFR 310.547
                  Created by admin on Sat Jun 26 08:53:52 UTC 2021 , Edited by admin on Sat Jun 26 08:53:52 UTC 2021
                  Code System Code Type Description
                  ECHA (EC/EINECS)
                  205-002-7
                  Created by admin on Sat Jun 26 08:53:52 UTC 2021 , Edited by admin on Sat Jun 26 08:53:52 UTC 2021
                  PRIMARY
                  EVMPD
                  SUB15091MIG
                  Created by admin on Sat Jun 26 08:53:52 UTC 2021 , Edited by admin on Sat Jun 26 08:53:52 UTC 2021
                  PRIMARY
                  EPA CompTox
                  130-90-5
                  Created by admin on Sat Jun 26 08:53:52 UTC 2021 , Edited by admin on Sat Jun 26 08:53:52 UTC 2021
                  PRIMARY
                  CAS
                  130-90-5
                  Created by admin on Sat Jun 26 08:53:52 UTC 2021 , Edited by admin on Sat Jun 26 08:53:52 UTC 2021
                  PRIMARY
                  FDA UNII
                  F87792011E
                  Created by admin on Sat Jun 26 08:53:52 UTC 2021 , Edited by admin on Sat Jun 26 08:53:52 UTC 2021
                  PRIMARY
                  PUBCHEM
                  9864167
                  Created by admin on Sat Jun 26 08:53:52 UTC 2021 , Edited by admin on Sat Jun 26 08:53:52 UTC 2021
                  PRIMARY
                  Related Record Type Details
                  PARENT -> SALT/SOLVATE
                  PARENT -> SALT/SOLVATE
                  Related Record Type Details
                  ACTIVE MOIETY