quinine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
4523 130-95-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • quinine bisulfate heptahydrate
  • chinine
  • qualaquin
  • quinine
  • quinine sulfate
An alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood.
  • Molecular weight: 324.42
  • Formula: C20H24N2O2
  • CLOGP: 2.79
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 45.59
  • ALOGS: -2.99
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.50 g O
1.50 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 111.10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 12 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 71.07 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.80 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.30 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 11 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 12, 2005 FDA MUTUAL PHARM CO INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 650.88 69.77 127 334 11899 2345725
Toxicity to various agents 224.46 69.77 66 395 32688 2324936
Drug hypersensitivity 173.11 69.77 59 402 46584 2311040
Electrocardiogram QT prolonged 125.00 69.77 31 430 7783 2349841
Renal failure 104.80 69.77 32 429 17317 2340307
Labile blood pressure 94.77 69.77 14 447 209 2357415
Thrombotic microangiopathy 87.88 69.77 17 444 1330 2356294
Sacroiliitis 83.88 69.77 13 448 271 2357353
Somatic symptom disorder 82.05 69.77 13 448 314 2357310
Retinal toxicity 73.02 69.77 11 450 188 2357436

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 2200.32 118.72 398 256 13291 1732836
Toxicity to various agents 534.70 118.72 151 503 28990 1717137
Poisoning 204.78 118.72 44 610 2488 1743639
Intentional product misuse 181.51 118.72 49 605 7309 1738818
Death 132.68 118.72 76 578 87367 1658760

Pharmacologic Action:

SourceCodeDescription
ATC M09AA72 MUSCULO-SKELETAL SYSTEM
OTHER DRUGS FOR DISORDERS OF THE MUSCULO-SKELETAL SYSTEM
OTHER DRUGS FOR DISORDERS OF THE MUSCULO-SKELETAL SYSTEM
Quinine and derivatives
ATC P01BC01 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Methanolquinolines
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D009125 Muscle Relaxants, Central
MeSH PA D009465 Neuromuscular Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:38068 antimalarial
CHEBI has role CHEBI:51371 muscle relaxant

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Falciparum malaria indication 62676009 DOID:14067
Chloroquine Resistant Plasmodium Falciparum Malaria indication
Babesiosis off-label use 21061004 DOID:9643
Atrial flutter contraindication 5370000
Torsades de pointes contraindication 31722008
End stage renal disease contraindication 46177005 DOID:784
Atrial fibrillation contraindication 49436004 DOID:0060224
Neuromuscular block, function contraindication 55394004
Black water fever contraindication 56625005 DOID:14068
Acute nephropathy contraindication 58574008
Optic neuritis contraindication 66760008 DOID:1210
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Myasthenia gravis contraindication 91637004 DOID:437
Hemolytic uremic syndrome contraindication 111407006 DOID:12554
Anemia due to enzyme deficiency contraindication 111577008
Prolonged QT interval contraindication 111975006
Disease of liver contraindication 235856003 DOID:409
Hypoglycemic disorder contraindication 237630007
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.44 acidic
pKa2 8.02 Basic
pKa3 4.1 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Hemoglobin subunit alpha Secreted WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel WOMBAT-PK
Equilibrative nucleoside transporter 4 Transporter INHIBITOR Ki 4.57 IUPHAR
Potassium voltage-gated channel subfamily B member 2 Ion channel BLOCKER IC50 4.90 IUPHAR
Multidrug resistance protein 1 Transporter Ki 4.92 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.29 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.36 CHEMBL

External reference:

IDSource
D08460 KEGG_DRUG
C1740885 UMLSCUI
A7V27PHC7A UNII
CHEMBL170 ChEMBL_ID
DB00468 DRUGBANK_ID
6183-68-2 SECONDARY_CAS_RN
QI9 PDB_CHEM_ID
CHEBI:15854 CHEBI
D011803 MESH_DESCRIPTOR_UI
CHEMBL2359966 ChEMBL_ID
3034034 PUBCHEM_CID
2510 IUPHAR_LIGAND_ID
47065008 SNOMEDCT_US
4019926 VANDF
9071 RXNORM
373497008 SNOMEDCT_US
d00366 MMSL
002934 NDDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Quinine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0093-3002 CAPSULE 324 mg ORAL ANDA 20 sections
Qualaquin HUMAN PRESCRIPTION DRUG LABEL 1 13310-153 CAPSULE 324 mg ORAL NDA 19 sections
QUALAQUIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-595 CAPSULE 324 mg ORAL NDA 19 sections
Qualaquin HUMAN PRESCRIPTION DRUG LABEL 1 49708-153 CAPSULE 324 mg ORAL NDA 20 sections
QUININE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 50742-238 CAPSULE 324 mg ORAL ANDA 20 sections
Quinine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 53489-700 CAPSULE 324 mg ORAL NDA authorized generic 20 sections
Quinine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 65162-811 CAPSULE 324 mg ORAL ANDA 20 sections
Quinine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 68084-947 CAPSULE 324 mg ORAL NDA authorized generic 19 sections
QUININE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 68180-560 CAPSULE 324 mg ORAL ANDA 18 sections