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 189.73 13.39 144 11579 63264 46611075
Labile blood pressure 119.65 13.39 35 11688 1668 46672671
Sacroiliitis 90.85 13.39 30 11693 2139 46672200
Somatic symptom disorder 90.45 13.39 29 11694 1883 46672456
Haematemesis 57.89 13.39 52 11671 28754 46645585
Hepatic ischaemia 47.30 13.39 13 11710 493 46673846
Coronary artery disease 47.29 13.39 50 11673 33702 46640637
Hepatorenal syndrome 45.06 13.39 17 11706 1791 46672548
Hepatic failure 44.17 13.39 48 11675 33368 46640971
Thrombotic microangiopathy 41.71 13.39 26 11697 8280 46666059
Muscle relaxant therapy 41.68 13.39 9 11714 120 46674219
Electrocardiogram QT prolonged 39.24 13.39 56 11667 51269 46623070
Renal failure 38.69 13.39 87 11636 113507 46560832
Lipase increased 38.40 13.39 25 11698 8578 46665761
Mood altered 37.62 13.39 29 11694 12978 46661361
Fear of eating 37.44 13.39 10 11713 340 46673999
Duodenal ulcer 37.27 13.39 23 11700 7195 46667144
Hyponatraemia 34.94 13.39 78 11645 101254 46573085
Rheumatoid arthritis 34.31 13.39 9 11714 240206 46434133
Drug ineffective 32.51 13.39 77 11646 677761 45996578
Plasmodium falciparum infection 30.68 13.39 6 11717 47 46674292
Coagulopathy 30.63 13.39 30 11693 18469 46655870
Retinal toxicity 30.08 13.39 11 11712 1062 46673277
Off label use 29.72 13.39 31 11692 379810 46294529
Product dose omission issue 28.94 13.39 4 11719 168516 46505823
Drug hypersensitivity 27.07 13.39 127 11596 243698 46430641
Cinchonism 26.39 13.39 4 11719 4 46674335
Swollen tongue 25.49 13.39 34 11689 29198 46645141
Vascular injury 24.95 13.39 9 11714 835 46673504
Blood sodium decreased 24.93 13.39 29 11694 21697 46652642
Toxicity to various agents 24.75 13.39 112 11611 211654 46462685
Vestibular disorder 24.07 13.39 10 11713 1356 46672983
Rhabdomyolysis 23.97 13.39 40 11683 41869 46632470
Optic ischaemic neuropathy 23.80 13.39 9 11714 954 46673385
Purpura senile 23.49 13.39 8 11715 627 46673712
Fatigue 23.30 13.39 77 11646 608620 46065719
Tarsal tunnel syndrome 23.24 13.39 8 11715 647 46673692
Salivary gland enlargement 23.09 13.39 7 11716 377 46673962
Oral cavity fistula 22.48 13.39 8 11715 714 46673625
Fibromyalgia 22.48 13.39 36 11687 36427 46637912
Hypovolaemia 22.16 13.39 19 11704 9869 46664470
Myocardial ischaemia 21.72 13.39 21 11702 12728 46661611
Exostosis of jaw 21.62 13.39 9 11714 1227 46673112
Muscle necrosis 20.45 13.39 7 11716 557 46673782
Eczema asteatotic 20.44 13.39 6 11717 289 46674050
Cerebral artery occlusion 20.31 13.39 8 11715 946 46673393
Abdominal rigidity 19.27 13.39 9 11714 1613 46672726
Resorption bone increased 19.02 13.39 8 11715 1119 46673220
Gastrointestinal haemorrhage 18.67 13.39 52 11671 77321 46597018
Exposed bone in jaw 18.57 13.39 11 11712 3197 46671142
Haemolytic uraemic syndrome 18.26 13.39 10 11713 2504 46671835
Cognitive disorder 18.22 13.39 33 11690 36850 46637489
Acute kidney injury 18.07 13.39 111 11612 235744 46438595
Adrenal mass 17.72 13.39 7 11716 834 46673505
Injection site pain 17.35 13.39 3 11720 107149 46567190
Drug intolerance 16.73 13.39 8 11715 147041 46527298
Coronary artery bypass 15.78 13.39 9 11714 2436 46671903
Agitated depression 15.12 13.39 4 11719 131 46674208
Completed suicide 15.04 13.39 9 11714 145911 46528428
Rectal haemorrhage 14.95 13.39 31 11692 38224 46636115
Gastritis 14.79 13.39 29 11694 34349 46639990
Confusional state 14.69 13.39 79 11644 159813 46514526
Somnambulism 14.06 13.39 11 11712 5026 46669313
Infusion related reaction 14.04 13.39 4 11719 101204 46573135
Fall 14.02 13.39 135 11588 328962 46345377
Bradycardia 13.54 13.39 42 11681 66256 46608083
Pharyngeal hypoaesthesia 13.43 13.39 4 11719 203 46674136

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 1039.00 17.69 461 6527 81611 29863879
Toxicity to various agents 222.77 17.69 238 6750 176945 29768545
Poisoning 85.14 17.69 45 6943 11337 29934153
Intentional product misuse 54.87 17.69 53 6935 34614 29910876
Exposure via ingestion 53.98 17.69 21 6967 2590 29942900
Compartment syndrome 47.60 17.69 19 6969 2508 29942982
Electrocardiogram U wave present 42.37 17.69 7 6981 19 29945471
Atrioventricular block 36.07 17.69 22 6966 7260 29938230
Cinchonism 33.88 17.69 5 6983 4 29945486
Muscle spasms 33.87 17.69 57 6931 64781 29880709
Hypomagnesaemia 33.31 17.69 29 6959 16569 29928921
Mouth swelling 30.03 17.69 12 6976 1587 29943903
Urine sodium decreased 28.41 17.69 7 6981 185 29945305
Agitated depression 26.83 17.69 7 6981 234 29945256
Lower respiratory tract infection 26.63 17.69 32 6956 26682 29918808
Nephrogenic systemic fibrosis 23.71 17.69 14 6974 4357 29941133
Drug ineffective 22.42 17.69 28 6960 340359 29605131
Cerebral malaria 22.09 17.69 3 6985 0 29945490
Malaria 22.08 17.69 6 6982 235 29945255
Increased bronchial secretion 21.44 17.69 9 6979 1350 29944140
Infected skin ulcer 20.93 17.69 9 6979 1431 29944059
Alveolar proteinosis 20.80 17.69 6 6982 293 29945197
Bradycardia 20.03 17.69 46 6942 65480 29880010
Body mass index decreased 19.28 17.69 5 6983 163 29945327
Cutaneous extramedullary haemopoiesis 18.80 17.69 3 6985 6 29945484
Blood magnesium decreased 18.43 17.69 13 6975 5470 29940020

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

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