chloroquine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
quinoline derivatives 607 54-05-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • chloroquine sulfate
  • chloroquine
  • chloroquine phosphate
  • chloraquine
  • chlorochin
  • chloroquine hydrochloride
  • chloroquine diphosphate
  • chloroquine HCl
  • chloroquine sulphate
The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. In March 2020, FDA issued an emergency use authorization (EUA) for hydroxychloroquine and chloroquine in the treatment of COVID-10. EUA was revoked in June 2020. Data from various published randomized, controlled clinical trials and retrospective, cohort studies have not substantiated initial reports of efficacy of 4-aminoquinoline antimalarials for treatment of COVID-19.
  • Molecular weight: 319.88
  • Formula: C18H26ClN3
  • CLOGP: 5.06
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 1
  • TPSA: 28.16
  • ALOGS: -4.26
  • ROTB: 8
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.50 g O
0.50 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 50 mg/mL Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine) 61 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 46.89 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 140 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 4.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.43 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 570 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 31, 1949 FDA SANOFI AVENTIS US

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
Necrotising herpetic retinopathy 68.35 18.47 11 5355 85 63483571
Off label use 58.98 18.47 156 5210 674306 62809350
Atrioventricular block complete 58.15 18.47 23 5343 8228 63475428
Weber tuning fork test abnormal 52.19 18.47 9 5357 110 63483546
Treatment failure 51.26 18.47 73 5293 198970 63284686
Retinal toxicity 49.43 18.47 13 5353 1262 63482394
Central nervous system lymphoma 38.22 18.47 11 5355 1491 63482165
Amaurosis 37.53 18.47 9 5357 600 63483056
Rheumatoid arthritis 36.87 18.47 72 5294 253747 63229909
Condition aggravated 33.91 18.47 92 5274 402125 63081531
Maculopathy 33.78 18.47 11 5355 2251 63481405
Cutaneous leishmaniasis 33.46 18.47 6 5360 93 63483563
C-reactive protein increased 32.46 18.47 40 5326 94667 63388989
Ocular toxicity 31.21 18.47 8 5358 702 63482954
Exposure via skin contact 30.28 18.47 7 5359 398 63483258
Ventricular hypertrophy 29.28 18.47 11 5355 3425 63480231
Toxic encephalopathy 28.55 18.47 13 5353 6566 63477090
Cardiotoxicity 28.41 18.47 14 5352 8424 63475232
Carcinoembryonic antigen increased 28.06 18.47 9 5357 1756 63481900
Disseminated tuberculosis 27.45 18.47 10 5356 2857 63480799
Drug ineffective 27.02 18.47 165 5201 1044600 62439056
Areflexia 26.63 18.47 10 5356 3108 63480548
Pulmonary fibrosis 26.56 18.47 24 5342 39785 63443871
Mucocutaneous leishmaniasis 25.29 18.47 6 5360 382 63483274
Torsade de pointes 24.96 18.47 15 5351 13336 63470320
Cardiomyopathy 23.53 18.47 16 5350 17568 63466088
Cinchonism 22.60 18.47 3 5363 4 63483652
Electrocardiogram QT prolonged 21.78 18.47 26 5340 59504 63424152
Nerve degeneration 21.69 18.47 4 5362 73 63483583
Restrictive cardiomyopathy 21.02 18.47 5 5361 322 63483334
Choking 20.83 18.47 12 5354 9867 63473789
Acquired pigmented retinopathy 20.31 18.47 3 5363 12 63483644
Synovitis 19.05 18.47 46 5320 186872 63296784
Glomerulonephritis chronic 18.88 18.47 4 5362 152 63483504

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
Off label use 248.76 30.96 185 1543 419339 34535864
Maculopathy 38.41 30.96 9 1719 937 34954266
Dry gangrene 33.47 30.96 7 1721 432 34954771
Pneumococcal infection 32.94 30.96 7 1721 467 34954736
Malaria 31.82 30.96 6 1722 217 34954986

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
Off label use 240.58 19.05 327 6112 906888 78831061
Atrioventricular block complete 70.92 19.05 32 6407 16578 79721371
Necrotising herpetic retinopathy 65.78 19.05 11 6428 116 79737833
Maculopathy 60.88 19.05 18 6421 2807 79735142
Weber tuning fork test abnormal 52.60 19.05 9 6430 110 79737839
Cardiotoxicity 41.17 19.05 20 6419 12219 79725730
Drug ineffective 35.34 19.05 176 6263 1080737 78657212
Central nervous system lymphoma 34.14 19.05 11 6428 2278 79735671
Restrictive cardiomyopathy 33.44 19.05 9 6430 999 79736950
Treatment failure 32.34 19.05 53 6386 170433 79567516
Exposure via skin contact 32.05 19.05 7 6432 322 79737627
Amaurosis 31.95 19.05 9 6430 1182 79736767
Electrocardiogram QT prolonged 30.43 19.05 37 6402 90349 79647600
Plasmodium vivax infection 28.69 19.05 4 6435 10 79737939
Acquired pigmented retinopathy 27.91 19.05 4 6435 13 79737936
Cutaneous leishmaniasis 26.81 19.05 6 6433 309 79737640
Carcinoembryonic antigen increased 26.48 19.05 9 6430 2200 79735749
Malaria 25.06 19.05 6 6433 416 79737533
Areflexia 24.69 19.05 11 6428 5523 79732426
Pneumococcal infection 24.62 19.05 7 6432 951 79736998
Dry gangrene 24.40 19.05 7 6432 982 79736967
Mucocutaneous leishmaniasis 24.30 19.05 6 6433 474 79737475
Condition aggravated 24.24 19.05 92 6347 501032 79236917
Disseminated tuberculosis 24.23 19.05 10 6429 4173 79733776
Liver injury 23.80 19.05 26 6413 56588 79681361
Torsade de pointes 22.83 19.05 16 6423 19296 79718653
Rheumatoid arthritis 22.46 19.05 51 6388 208419 79529530
Ventricular hypertrophy 22.32 19.05 11 6428 6927 79731022
Toxic encephalopathy 22.31 19.05 13 6426 11427 79726522
Retinal toxicity 21.94 19.05 7 6432 1404 79736545
Methaemoglobinaemia 21.50 19.05 10 6429 5547 79732402
Ocular toxicity 20.68 19.05 6 6433 875 79737074
Pulmonary fibrosis 19.85 19.05 21 6418 44091 79693858
Optic atrophy 19.78 19.05 7 6432 1926 79736023
Post inflammatory pigmentation change 19.42 19.05 5 6434 467 79737482
Cinchonism 19.30 19.05 3 6436 19 79737930
Cardiomyopathy 19.17 19.05 17 6422 28757 79709192
C-reactive protein increased 19.11 19.05 36 6403 128991 79608958

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC P01BA01 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Aminoquinolines
ATC P01BB52 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Biguanides
FDA EPC N0000175482 Antimalarial
CHEBI has role CHEBI:35842 anti-rheumatic drugs
CHEBI has role CHEBI:38068 antimalarials
CHEBI has role CHEBI:50177 dermatologic agent
CHEBI has role CHEBI:88230 autophagy inhibitors
CHEBI has role CHEBI:149553 anticoronaviral drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000871 Anthelmintics
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D000962 Antimalarials
MeSH PA D000969 Antinematodal Agents
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D005369 Filaricides
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D000563 Amebicides

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Ovale malaria indication 19341001 DOID:12919
Vivax malaria indication 27052006 DOID:12978
Quartan malaria indication 27618009 DOID:14324
Systemic lupus erythematosus indication 55464009 DOID:9074
Falciparum malaria indication 62676009 DOID:14067
Rheumatoid arthritis indication 69896004 DOID:7148
Discoid lupus erythematosus indication 200938002
Plasmodium Malariae Malaria Prevention indication
Plasmodium Ovale Malaria Prevention indication
Malaria Prevention indication
Plasmodium Falciparum Malaria Prevention indication
Vasculitis of the skin off-label use 53312001
Porphyria cutanea tarda off-label use 61860000 DOID:3132
Q fever endocarditis off-label use 95890006
Coronavirus infection off-label use 186747009
Polymorphic light eruption off-label use 238525001
Juvenile rheumatoid arthritis off-label use 410795001
Hypercalcemia associated with Sarcoidosis off-label use
Alcoholism contraindication 7200002
Psoriasis contraindication 9014002 DOID:8893
Visual field defect contraindication 12184005
Retinal disorder contraindication 29555009 DOID:5679
Leukopenia contraindication 84828003 DOID:615
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Hearing disorder contraindication 128540005
Seizure disorder contraindication 128613002
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Neutropenic disorder contraindication 303011007 DOID:1227
Disorder of macula of retina contraindication 312999006
Disorder of eye contraindication 371405004 DOID:5614
Visual impairment contraindication 397540003
Porphyria contraindication 418470004




🐶 Veterinary Drug Use

SpeciesUseRelation
Dogs Euthanasia Indication

🐶 Veterinary products

ProductApplicantIngredients
Tributame Euthanasia Solution Cronus Pharma Specialities India Private Limited 3

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.19 Basic
pKa2 7.83 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 IC50 5.60 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 5.36 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.10 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 4.50 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 5.04 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 5.33 CHEMBL
Muscarinic acetylcholine receptor M3 GPCR Ki 5.48 CHEMBL
Muscarinic acetylcholine receptor M4 GPCR Ki 5.24 CHEMBL
Muscarinic acetylcholine receptor M5 GPCR Ki 4.66 CHEMBL
Alpha-2C adrenergic receptor GPCR Ki 5 CHEMBL
Ribosyldihydronicotinamide dehydrogenase [quinone] Enzyme IC50 5.82 CHEMBL
Serine/threonine-protein kinase mTOR Kinase IC50 6.57 CHEMBL
Beta-secretase 1 Enzyme IC50 5.16 CHEMBL
Major prion protein Surface antigen EC50 5.40 CHEMBL
Amyloid beta A4 protein Unclassified IC50 5.16 CHEMBL
Transmembrane protein 97 Enzyme Ki 6.30 CHEMBL
Nuclear receptor subfamily 4 group A member 2 Nuclear other EC50 4.33 CHEMBL
Histidine-rich protein PFHRP-II Cytosolic other IC50 6.40 CHEMBL
Riboflavin-binding protein Unclassified Kd 5.68 CHEMBL
Dihydrofolate reductase Enzyme IC50 7.52 CHEMBL
Spike glycoprotein Glycoprotein IC50 6.80 CHEMBL
Cysteine proteinase falcipain 2a Enzyme IC50 7.70 CHEMBL
Cysteine proteinase falcipain 2a Enzyme IC50 6.70 CHEMBL

External reference:

IDSource
D02125 KEGG_DRUG
132-73-0 SECONDARY_CAS_RN
50-63-5 SECONDARY_CAS_RN
3545-67-3 SECONDARY_CAS_RN
203119 RXNORM
4018227 VANDF
4018228 VANDF
4019675 VANDF
C0008269 UMLSCUI
CHEBI:3638 CHEBI
CLQ PDB_CHEM_ID
CHEMBL1326 ChEMBL_ID
CHEMBL76 ChEMBL_ID
CHEMBL250447 ChEMBL_ID
CHEMBL2095223 ChEMBL_ID
DB00608 DRUGBANK_ID
CHEMBL58510 ChEMBL_ID
D002738 MESH_DESCRIPTOR_UI
2719 PUBCHEM_CID
5535 IUPHAR_LIGAND_ID
C023676 MESH_SUPPLEMENTAL_RECORD_UI
386 INN_ID
886U3H6UFF UNII
3949 MMSL
4417 MMSL
4418 MMSL
d00035 MMSL
002938 NDDF
002939 NDDF
002940 NDDF
004124 NDDF
14728000 SNOMEDCT_US
373468005 SNOMEDCT_US
395937005 SNOMEDCT_US
53136009 SNOMEDCT_US
60266005 SNOMEDCT_US
CHEMBL4297165 ChEMBL_ID
CHEMBL1669 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 0115-2790 TABLET 250 mg ORAL ANDA 13 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 0115-7010 TABLET 500 mg ORAL ANDA 20 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 23155-850 TABLET, COATED 500 mg ORAL ANDA 22 sections
Chloroquine Phosphate Human Prescription Drug Label 1 50090-4967 TABLET 250 mg ORAL ANDA 14 sections
Chloroquine Phosphate Human Prescription Drug Label 1 50090-4967 TABLET 250 mg ORAL ANDA 14 sections
CHLOROQUINE PHOSPHATE HUMAN PRESCRIPTION DRUG LABEL 1 62135-717 TABLET, COATED 500 mg ORAL ANDA 12 sections
Chloroquine Phosphate Human Prescription Drug Label 1 64980-177 TABLET 250 mg ORAL ANDA 14 sections
Chloroquine Phosphate Human Prescription Drug Label 1 64980-178 TABLET 500 mg ORAL ANDA 15 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 68022-0264 TABLET, COATED 500 mg ORAL ANDA 22 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 68022-0264 TABLET, COATED 500 mg ORAL ANDA 22 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 68022-0264 TABLET, COATED 500 mg ORAL ANDA 22 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 68022-0265 TABLET, COATED 500 mg ORAL ANDA 22 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 68022-0265 TABLET, COATED 500 mg ORAL ANDA 22 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 68022-0265 TABLET, COATED 500 mg ORAL ANDA 22 sections
Chloroquine phosphate HUMAN PRESCRIPTION DRUG LABEL 1 76385-142 TABLET, FILM COATED 250 mg ORAL ANDA 18 sections
Chloroquine phosphate HUMAN PRESCRIPTION DRUG LABEL 1 76385-142 TABLET, FILM COATED 250 mg ORAL ANDA 18 sections