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 200.61 13.61 147 12403 65379 53271137
Labile blood pressure 149.89 13.61 42 12508 1832 53334684
Somatic symptom disorder 89.66 13.61 29 12521 2069 53334447
Sacroiliitis 88.58 13.61 30 12520 2470 53334046
Hepatic ischaemia 77.40 13.61 20 12530 638 53335878
Lipase increased 72.42 13.61 38 12512 9340 53327176
Haematemesis 71.99 13.61 59 12491 30798 53305718
Hepatorenal syndrome 70.34 13.61 24 12526 2021 53334495
Hepatic failure 56.71 13.61 55 12495 35751 53300765
Muscle relaxant therapy 54.49 13.61 12 12538 189 53336327
Coronary artery disease 50.41 13.61 50 12500 33387 53303129
Renal failure 48.34 13.61 94 12456 118358 53218158
Rheumatoid arthritis 46.20 13.61 9 12541 314522 53021994
Coagulopathy 44.54 13.61 37 12513 19661 53316855
Thrombotic microangiopathy 42.96 13.61 27 12523 9310 53327206
Hyponatraemia 42.87 13.61 85 12465 108522 53227994
Drug ineffective 40.87 13.61 82 12468 817163 52519353
Electrocardiogram QT prolonged 39.43 13.61 57 12493 56346 53280170
Toxicity to various agents 38.22 13.61 126 12424 219472 53117044
Hypovolaemia 37.91 13.61 26 12524 10376 53326140
Mood altered 37.59 13.61 29 12521 13872 53322644
Duodenal ulcer 37.46 13.61 23 12527 7613 53328903
Drug hypersensitivity 37.42 13.61 142 12408 265100 53071416
Fear of eating 36.93 13.61 10 12540 383 53336133
Off label use 34.75 13.61 36 12514 472176 52864340
Gastrointestinal haemorrhage 33.05 13.61 64 12486 80266 53256250
Post procedural haemorrhage 31.63 13.61 21 12529 7947 53328569
Product dose omission issue 31.46 13.61 4 12546 191616 53144900
Coronary artery bypass 31.09 13.61 14 12536 2464 53334052
Plasmodium falciparum infection 31.07 13.61 6 12544 47 53336469
Retinal toxicity 29.60 13.61 11 12539 1186 53335330
Cinchonism 26.65 13.61 4 12546 4 53336512
Drug intolerance 26.02 13.61 8 12542 205485 53131031
Swollen tongue 25.60 13.61 34 12516 31046 53305470
Vascular injury 25.40 13.61 9 12541 847 53335669
Fatigue 25.24 13.61 88 12462 730418 52606098
Blood sodium decreased 25.00 13.61 29 12521 23087 53313429
Rhabdomyolysis 24.51 13.61 40 12510 43883 53292633
Vestibular disorder 24.39 13.61 10 12540 1401 53335115
Purpura senile 24.16 13.61 8 12542 614 53335902
Cognitive disorder 23.94 13.61 40 12510 44738 53291778
Tarsal tunnel syndrome 23.88 13.61 8 12542 637 53335879
Infusion related reaction 23.87 13.61 4 12546 155953 53180563
Salivary gland enlargement 23.44 13.61 7 12543 383 53336133
Optic ischaemic neuropathy 23.24 13.61 9 12541 1087 53335429
Pancreatitis 23.06 13.61 40 12510 46102 53290414
Oral cavity fistula 23.02 13.61 8 12542 711 53335805
Myocardial ischaemia 22.75 13.61 21 12529 12823 53323693
Exostosis of jaw 21.96 13.61 9 12541 1260 53335256
Eczema asteatotic 20.89 13.61 6 12544 286 53336230
Muscle necrosis 20.69 13.61 7 12543 574 53335942
Cerebral artery occlusion 20.54 13.61 8 12542 980 53335536
Resorption bone increased 19.42 13.61 8 12542 1134 53335382
Ulcer 19.24 13.61 24 12526 20595 53315921
Fibromyalgia 19.21 13.61 36 12514 44039 53292477
Fall 19.18 13.61 147 12403 358293 52978223
Left ventricular dysfunction 19.18 13.61 18 12532 11219 53325297
Exposed bone in jaw 19.10 13.61 11 12539 3239 53333277
Hiccups 19.08 13.61 9 12541 1761 53334755
Haemolytic uraemic syndrome 18.70 13.61 10 12540 2551 53333965
Abdominal rigidity 18.64 13.61 9 12541 1855 53334661
Product use issue 18.46 13.61 5 12545 139579 53196937
Acute kidney injury 18.26 13.61 112 12438 253756 53082760
Adrenal mass 17.91 13.61 7 12543 866 53335650
Abdominal discomfort 17.20 13.61 16 12534 221046 53115470
Hepatocellular injury 16.31 13.61 27 12523 29959 53306557
Synovitis 16.00 13.61 3 12547 107890 53228626
Hepatic enzyme increased 15.81 13.61 5 12545 126190 53210326
Agitated depression 15.41 13.61 4 12546 130 53336386
Injection site pain 15.11 13.61 4 12546 113387 53223129
Gastritis 15.05 13.61 29 12521 36205 53300311
Muscle spasms 14.88 13.61 67 12483 134728 53201788
Nail infection 14.65 13.61 8 12542 2126 53334390
Myocardial infarction 14.63 13.61 54 12496 99300 53237216
Rectal haemorrhage 14.61 13.61 31 12519 41450 53295066
Somnambulism 14.02 13.61 11 12539 5391 53331125
Cerebrovascular accident 13.72 13.61 55 12495 105119 53231397

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 1071.78 16.58 465 6944 79778 32426339
Toxicity to various agents 242.66 16.58 247 7162 177794 32328323
Poisoning 86.97 16.58 45 7364 11113 32495004
Exposure via ingestion 56.55 16.58 21 7388 2336 32503781
Intentional product misuse 54.16 16.58 53 7356 35998 32470119
Compartment syndrome 47.67 16.58 19 7390 2558 32503559
Electrocardiogram U wave present 42.53 16.58 7 7402 19 32506098
Atrioventricular block 35.53 16.58 22 7387 7633 32498484
Cinchonism 34.00 16.58 5 7404 4 32506113
Muscle spasms 33.99 16.58 59 7350 70359 32435758
Toxic neuropathy 31.01 16.58 9 7400 460 32505657
Hypomagnesaemia 30.78 16.58 29 7380 18776 32487341
Mouth swelling 29.35 16.58 12 7397 1724 32504393
Urine sodium decreased 28.57 16.58 7 7402 185 32505932
Agitated depression 26.99 16.58 7 7402 234 32505883
Nephrogenic systemic fibrosis 24.07 16.58 14 7395 4338 32501779
Lower respiratory tract infection 23.36 16.58 31 7378 29212 32476905
Drug ineffective 22.45 16.58 33 7376 383444 32122673
Cerebral malaria 22.16 16.58 3 7406 0 32506117
Malaria 21.14 16.58 6 7403 283 32505834
Blood sodium decreased 20.68 16.58 22 7387 16452 32489665
Infected skin ulcer 20.66 16.58 9 7400 1512 32504605
Alveolar proteinosis 20.02 16.58 6 7403 343 32505774
Increased bronchial secretion 19.40 16.58 9 7400 1752 32504365
Hypocalcaemia 19.28 16.58 25 7384 23029 32483088
Body mass index decreased 19.11 16.58 5 7404 173 32505944
Cutaneous extramedullary haemopoiesis 18.87 16.58 3 7406 6 32506111
Lethargy 17.89 16.58 33 7376 41195 32464922
Skin induration 17.39 16.58 9 7400 2219 32503898
Bradycardia 17.04 16.58 45 7364 71517 32434600
Restless legs syndrome 16.96 16.58 14 7395 7610 32498507

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
FDA EPC N0000175482 Antimalarial
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:38068 antimalarials
CHEBI has role CHEBI:51371 muscle relaxants

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
Potassium voltage-gated channel subfamily H member 2 Ion channel WOMBAT-PK
Multidrug resistance protein 1 Transporter Ki 4.92 CHEMBL
Hemoglobin subunit alpha Secreted WOMBAT-PK
Potassium voltage-gated channel subfamily B member 2 Ion channel BLOCKER IC50 4.90 IUPHAR
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
Equilibrative nucleoside transporter 4 Transporter INHIBITOR Ki 4.57 IUPHAR

External reference:

IDSource
D08460 KEGG_DRUG
6183-68-2 SECONDARY_CAS_RN
4018620 VANDF
4019926 VANDF
CHEBI:15854 CHEBI
QI9 PDB_CHEM_ID
CHEMBL170 ChEMBL_ID
CHEMBL2359966 ChEMBL_ID
2510 IUPHAR_LIGAND_ID
DB00468 DRUGBANK_ID
A7V27PHC7A UNII
3034034 PUBCHEM_CID
647128 RXNORM
5023 MMSL
5405 MMSL
84102 MMSL
d00366 MMSL
002934 NDDF
002935 NDDF
373497008 SNOMEDCT_US
47065008 SNOMEDCT_US
47857006 SNOMEDCT_US
D011803 MESH_DESCRIPTOR_UI
C0034417 UMLSCUI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Quinine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0093-3002 CAPSULE 324 mg ORAL ANDA 31 sections
Qualaquin HUMAN PRESCRIPTION DRUG LABEL 1 13310-153 CAPSULE 324 mg ORAL NDA 32 sections
QUALAQUIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-595 CAPSULE 324 mg ORAL NDA 32 sections
Qualaquin HUMAN PRESCRIPTION DRUG LABEL 1 49708-153 CAPSULE 324 mg ORAL NDA 32 sections
QUININE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 50742-238 CAPSULE 324 mg ORAL ANDA 21 sections
Quinine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 53489-700 CAPSULE 324 mg ORAL NDA authorized generic 32 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 31 sections
QUININE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 68180-560 CAPSULE 324 mg ORAL ANDA 20 sections