quinine ๐Ÿถ Veterinary Use | 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 ยตM/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 208.16 13.42 148 12379 59698 50532899
Labile blood pressure 152.82 13.42 42 12485 1618 50590979
Somatic symptom disorder 94.50 13.42 30 12497 1914 50590683
Sacroiliitis 89.83 13.42 31 12496 2566 50590031
Lipase increased 82.73 13.42 41 12486 8500 50584097
Hepatic ischaemia 78.05 13.42 20 12507 585 50592012
Haematemesis 74.90 13.42 59 12468 27666 50564931
Hepatorenal syndrome 72.90 13.42 24 12503 1719 50590878
Hepatic failure 59.17 13.42 55 12472 32228 50560369
Muscle relaxant therapy 55.47 13.42 12 12515 164 50592433
Coronary artery disease 53.24 13.42 50 12477 29676 50562921
Renal failure 48.19 13.42 91 12436 106542 50486055
Drug ineffective 46.24 13.42 83 12444 819250 49773347
Coagulopathy 45.92 13.42 37 12490 17907 50574690
Hyponatraemia 43.38 13.42 82 12445 96057 50496540
Thrombotic microangiopathy 43.19 13.42 27 12500 8764 50583833
Drug hypersensitivity 41.14 13.42 146 12381 250864 50341733
Electrocardiogram QT prolonged 40.86 13.42 57 12470 51829 50540768
Mood altered 40.69 13.42 30 12497 12743 50579854
Hypovolaemia 38.94 13.42 26 12501 9439 50583158
Duodenal ulcer 38.92 13.42 23 12504 6752 50585845
Toxicity to various agents 38.66 13.42 128 12399 212371 50380226
Fear of eating 37.86 13.42 10 12517 330 50592267
Gastrointestinal haemorrhage 33.63 13.42 63 12464 73258 50519339
Off label use 33.53 13.42 41 12486 474385 50118212
Post procedural haemorrhage 32.41 13.42 21 12506 7249 50585348
Product dose omission issue 31.85 13.42 4 12523 183834 50408763
Coronary artery bypass 31.45 13.42 14 12513 2279 50590318
Drug intolerance 31.01 13.42 8 12519 219096 50373501
Cognitive disorder 29.68 13.42 45 12482 44078 50548519
Retinal toxicity 29.14 13.42 11 12516 1177 50591420
Infusion related reaction 28.63 13.42 4 12523 169553 50423044
Pancreatitis 28.01 13.42 43 12484 42571 50550026
Cinchonism 26.98 13.42 4 12523 3 50592594
Rhabdomyolysis 26.53 13.42 40 12487 38987 50553610
Swollen tongue 26.43 13.42 34 12493 28596 50564001
Fatigue 26.20 13.42 89 12438 707512 49885085
Blood sodium decreased 25.90 13.42 29 12498 21118 50571479
Rheumatoid arthritis 25.75 13.42 9 12518 202541 50390056
Purpura senile 25.03 13.42 8 12519 521 50592076
Vestibular disorder 24.92 13.42 10 12517 1259 50591338
Tarsal tunnel syndrome 24.89 13.42 8 12519 531 50592066
Vascular injury 24.86 13.42 9 12518 856 50591741
Myocardial ischaemia 23.65 13.42 21 12506 11592 50581005
Oral cavity fistula 23.50 13.42 8 12519 635 50591962
Salivary gland enlargement 23.47 13.42 7 12520 362 50592235
Optic ischaemic neuropathy 23.44 13.42 9 12518 1008 50591589
Product use issue 22.04 13.42 5 12522 149470 50443127
Hiccups 21.89 13.42 10 12517 1729 50590868
Exostosis of jaw 21.86 13.42 9 12518 1210 50591387
Cerebral artery occlusion 21.23 13.42 8 12519 852 50591745
Muscle necrosis 21.21 13.42 7 12520 505 50592092
Eczema asteatotic 21.16 13.42 6 12521 259 50592338
Abdominal discomfort 20.99 13.42 16 12511 231625 50360972
Synovitis 20.72 13.42 3 12524 123862 50468735
Acute kidney injury 20.62 13.42 111 12416 227947 50364650
Exposed bone in jaw 20.11 13.42 11 12516 2789 50589808
Resorption bone increased 19.97 13.42 8 12519 1003 50591594
Fibromyalgia 19.81 13.42 38 12489 44940 50547657
Left ventricular dysfunction 19.43 13.42 18 12509 10488 50582109
Haemolytic uraemic syndrome 19.15 13.42 10 12517 2309 50590288
Abdominal rigidity 18.97 13.42 9 12518 1695 50590902
Ulcer 18.66 13.42 24 12503 20176 50572421
Adrenal mass 18.23 13.42 7 12520 785 50591812
Hepatocellular injury 18.21 13.42 27 12500 25920 50566677
Nail infection 17.68 13.42 9 12518 1972 50590625
Hepatic enzyme increased 17.63 13.42 6 12521 137374 50455223
Fall 17.46 13.42 142 12385 334790 50257807
Discomfort 17.28 13.42 3 12524 108377 50484220
Pain 16.83 13.42 80 12447 578823 50013774
Myocardial infarction 16.47 13.42 54 12473 88973 50503624
Cerebrovascular accident 16.26 13.42 56 12471 94624 50497973
Injection site pain 15.80 13.42 4 12523 111020 50481577
Therapeutic product effect decreased 15.71 13.42 7 12520 136043 50456554
Hand deformity 15.49 13.42 3 12524 100196 50492401
Agitated depression 15.45 13.42 4 12523 122 50592475
Rectal haemorrhage 15.08 13.42 31 12496 38527 50554070
Gastritis 14.69 13.42 28 12499 32955 50559642
Hyperkalaemia 14.67 13.42 35 12492 48054 50544543
Sequestrectomy 14.55 13.42 6 12521 810 50591787
Sedation complication 14.28 13.42 14 12513 8752 50583845
Sinusitis 13.94 13.42 13 12514 170545 50422052
Vaginal discharge 13.82 13.42 11 12516 5229 50587368
Disseminated intravascular coagulation 13.74 13.42 19 12508 17116 50575481
Multiple organ dysfunction syndrome 13.63 13.42 35 12492 50302 50542295
Nephrogenic systemic fibrosis 13.42 13.42 10 12517 4312 50588285

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 1059.02 16.22 469 6709 79414 29487935
Toxicity to various agents 254.88 16.22 258 6920 173403 29393946
Poisoning 88.98 16.22 45 7133 9948 29557401
Exposure via ingestion 58.44 16.22 21 7157 1997 29565352
Intentional product misuse 54.96 16.22 54 7124 34607 29532742
Compartment syndrome 47.42 16.22 19 7159 2433 29564916
Electrocardiogram U wave present 42.09 16.22 7 7171 19 29567330
Atrioventricular block 36.12 16.22 22 7156 6960 29560389
Cinchonism 33.68 16.22 5 7173 4 29567345
Toxic neuropathy 31.33 16.22 9 7169 416 29566933
Mouth swelling 29.74 16.22 12 7166 1564 29565785
Hypomagnesaemia 29.14 16.22 28 7150 17440 29549909
Urine sodium decreased 28.82 16.22 7 7171 167 29567182
Agitated depression 26.76 16.22 7 7171 227 29567122
Lower respiratory tract infection 25.82 16.22 32 7146 26470 29540879
Nephrogenic systemic fibrosis 24.53 16.22 14 7164 3928 29563421
Drug ineffective 22.94 16.22 33 7145 363137 29204212
Cerebral malaria 21.97 16.22 3 7175 0 29567349
Unresponsive to stimuli 20.81 16.22 28 7150 25098 29542251
Infected skin ulcer 20.73 16.22 9 7169 1408 29565941
Confusional state 20.60 16.22 73 7105 127804 29439545
Alveolar proteinosis 20.05 16.22 6 7172 320 29567029
Increased bronchial secretion 19.78 16.22 9 7169 1572 29565777
Body mass index decreased 19.39 16.22 5 7173 153 29567196
Cutaneous extramedullary haemopoiesis 18.68 16.22 3 7175 6 29567343
Hypocalcaemia 18.61 16.22 24 7154 20641 29546708
Lethargy 18.60 16.22 33 7145 37547 29529802
Blood sodium decreased 17.99 16.22 20 7158 14747 29552602
Skin induration 17.54 16.22 9 7169 2045 29565304

FDA Adverse Event Reporting System (Geriatric)

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 1178.78 13.28 620 17270 131754 64349088
Toxicity to various agents 229.89 13.28 382 17508 363131 64117711
Thrombotic microangiopathy 170.27 13.28 86 17804 16569 64464273
Labile blood pressure 134.43 13.28 41 17849 2039 64478803
Somatic symptom disorder 92.30 13.28 30 17860 1838 64479004
Sacroiliitis 81.89 13.28 31 17859 2981 64477861
Poisoning 76.82 13.28 57 17833 21822 64459020
Hepatic ischaemia 65.42 13.28 20 17870 1002 64479840
Drug ineffective 65.00 13.28 83 17807 840164 63640678
Exposure via ingestion 61.12 13.28 29 17861 4873 64475969
Cinchonism 59.54 13.28 9 17881 7 64480835
Haematemesis 57.44 13.28 68 17822 46931 64433911
Hepatorenal syndrome 55.57 13.28 25 17865 3721 64477121
Muscle relaxant therapy 54.11 13.28 12 17878 164 64480678
Hyponatraemia 53.03 13.28 123 17767 148216 64332626
Microangiopathic haemolytic anaemia 51.94 13.28 18 17872 1344 64479498
Intentional product misuse 45.40 13.28 76 17814 72219 64408623
Off label use 45.30 13.28 66 17824 632740 63848102
Acute kidney injury 44.30 13.28 243 17647 448997 64031845
Agitated depression 42.85 13.28 11 17879 288 64480554
Product dose omission issue 42.42 13.28 3 17887 194744 64286098
Atrioventricular block 39.28 13.28 30 17860 11985 64468857
Compartment syndrome 35.08 13.28 19 17871 4213 64476629
Blood sodium decreased 34.93 13.28 42 17848 29440 64451402
Fear of eating 34.76 13.28 10 17880 405 64480437
Mood altered 33.75 13.28 31 17859 15948 64464894
Retinal toxicity 33.68 13.28 13 17877 1317 64479525
Rhabdomyolysis 32.68 13.28 76 17814 91650 64389192
Coagulopathy 32.27 13.28 42 17848 31878 64448964
Coronary artery disease 30.81 13.28 58 17832 60375 64420467
Swollen tongue 30.78 13.28 43 17847 34911 64445931
Hypovolaemia 30.70 13.28 29 17861 15457 64465385
Electrocardiogram U wave present 30.36 13.28 7 17883 115 64480727
Hepatic failure 29.28 13.28 54 17836 55340 64425502
Nephrogenic systemic fibrosis 29.25 13.28 19 17871 5873 64474969
Duodenal ulcer 28.55 13.28 27 17863 14408 64466434
Renal failure 27.95 13.28 112 17778 181576 64299266
Rheumatoid arthritis 27.45 13.28 6 17884 164288 64316554
Exposed bone in jaw 27.09 13.28 15 17875 3472 64477370
Electrocardiogram QT prolonged 26.32 13.28 64 17826 79384 64401458
Fatigue 26.16 13.28 113 17777 748617 63732225
Post procedural haemorrhage 26.03 13.28 24 17866 12407 64468435
Toxic neuropathy 24.59 13.28 9 17881 787 64480055
Cognitive disorder 24.59 13.28 50 17840 55037 64425805
Tarsal tunnel syndrome 24.50 13.28 8 17882 497 64480345
Purpura senile 24.41 13.28 8 17882 503 64480339
Hypocalcaemia 23.72 13.28 42 17848 41711 64439131
Fall 23.26 13.28 196 17694 416630 64064212
Hypomagnesaemia 23.06 13.28 39 17851 37337 64443505
Lethargy 22.49 13.28 57 17833 72537 64408305
Salivary gland enlargement 22.42 13.28 7 17883 376 64480466
Vascular injury 22.18 13.28 9 17881 1040 64479802
Infusion related reaction 22.05 13.28 9 17881 164458 64316384
Cerebral malaria 21.57 13.28 3 17887 0 64480842
Cardiovascular disorder 21.10 13.28 24 17866 15857 64464985
Exostosis of jaw 21.05 13.28 9 17881 1185 64479657
Confusional state 20.97 13.28 134 17756 261010 64219832
Gastrointestinal haemorrhage 20.68 13.28 82 17808 132230 64348612
Contraindicated product administered 20.03 13.28 3 17887 107826 64373016
Ulcer 19.82 13.28 28 17862 22962 64457880
Drug intolerance 19.78 13.28 14 17876 187978 64292864
Myocardial ischaemia 19.57 13.28 28 17862 23223 64457619
Unresponsive to stimuli 19.32 13.28 43 17847 50350 64430492
Hepatic enzyme increased 19.31 13.28 6 17884 129937 64350905
Product use issue 19.23 13.28 9 17881 151706 64329136
Fibromyalgia 19.09 13.28 35 17855 35696 64445146
Bradycardia 19.07 13.28 74 17816 118145 64362697
Liver function test abnormal 18.77 13.28 47 17843 59354 64421488
Injection site pain 18.74 13.28 4 17886 111404 64369438
Oral cavity fistula 18.53 13.28 7 17883 669 64480173
Lower respiratory tract infection 18.45 13.28 63 17827 94551 64386291
Cerebrovascular accident 18.18 13.28 81 17809 137502 64343340
Treatment failure 18.08 13.28 5 17885 116811 64364031
Resorption bone increased 17.98 13.28 8 17882 1160 64479682
Synovitis 17.86 13.28 3 17887 99087 64381755
Melaena 17.59 13.28 43 17847 53505 64427337
Plasmodium falciparum infection 17.45 13.28 4 17886 64 64480778
Blindness transient 17.36 13.28 12 17878 4110 64476732
Nail infection 17.31 13.28 9 17881 1838 64479004
Skin induration 17.22 13.28 12 17878 4163 64476679
Eczema asteatotic 17.08 13.28 6 17884 466 64480376
Optic ischaemic neuropathy 17.07 13.28 10 17880 2575 64478267
Cardiac arrest 16.93 13.28 86 17804 153978 64326864
Blindness 16.35 13.28 25 17865 21994 64458848
Product use in unapproved indication 16.27 13.28 15 17875 176603 64304239
Alveolar proteinosis 15.88 13.28 6 17884 574 64480268
Coronary artery bypass 15.75 13.28 13 17877 5802 64475040
Cerebral artery occlusion 15.53 13.28 8 17882 1603 64479239
Lip swelling 15.49 13.28 30 17860 31877 64448965
Vestibular disorder 15.49 13.28 9 17881 2284 64478558
Vaginal discharge 15.35 13.28 11 17879 3986 64476856
Mouth swelling 15.06 13.28 12 17878 5095 64475747
Respiratory arrest 14.77 13.28 40 17850 52945 64427897
Muscle necrosis 14.53 13.28 7 17883 1216 64479626
Therapeutic product effect decreased 14.38 13.28 7 17883 115344 64365498
Abdominal rigidity 14.36 13.28 9 17881 2618 64478224
Depressed level of consciousness 13.97 13.28 52 17838 81384 64399458
International normalised ratio increased 13.96 13.28 51 17839 79116 64401726
Myocardial infarction 13.86 13.28 86 17804 165735 64315107
Increased bronchial secretion 13.71 13.28 9 17881 2833 64478009
Rectal haemorrhage 13.70 13.28 43 17847 61774 64419068
Sequestrectomy 13.66 13.28 6 17884 843 64479999
Left ventricular dysfunction 13.66 13.28 20 17870 16934 64463908

FDA Adverse Event Reporting System (Pediatric)

None

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 | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
6119-70-6 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 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