chloroquine 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.
  • Molecular weight: 319.88
  • Formula: C18H26ClN3
  • CLOGP: 5.06
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 1
  • TPSA: 28.16
  • ALOGS: -4.26
  • ROTB: 8

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) 100 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 61 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 46.89 ┬ÁM/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
Atrioventricular block complete 160.49 54.75 25 169 1389 2356502
Cardiotoxicity 104.34 54.75 17 177 1230 2356661
Ventricular hypertrophy 92.08 54.75 14 180 642 2357249
Toxicity to various agents 73.64 54.75 23 171 32731 2325160
Cardiomyopathy 65.63 54.75 13 181 2794 2355097
Intentional overdose 62.00 54.75 16 178 11305 2346586
Completed suicide 60.90 54.75 18 176 21016 2336875
Cardiac arrest 57.61 54.75 16 178 14914 2342977

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

Pharmacologic Action:

SourceCodeDescription
ATC P01BA01 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Aminoquinolines
MeSH PA D000563 Amebicides
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35842 antirheumatic drug
CHEBI has role CHEBI:50177 dermatologic drug
CHEBI has role CHEBI:38068 antimalarial
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

Drug Use (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

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
Major prion protein Surface antigen EC50 5.40 CHEMBL
Ribosyldihydronicotinamide dehydrogenase [quinone] Enzyme IC50 5.82 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.60 WOMBAT-PK
SARS-CoV-2 Virus INHIBITOR EC50 5.95 SCIENTIFIC LITERATURE
Histidine-rich protein PFHRP-II Cytosolic other IC50 6.40 CHEMBL
Riboflavin-binding protein Unclassified Kd 5.68 CHEMBL

External reference:

IDSource
D002738 MESH_DESCRIPTOR_UI
C0700447 UMLSCUI
D02125 KEGG_DRUG
6E17K3343P UNII
50-63-5 SECONDARY_CAS_RN
14728000 SNOMEDCT_US
4019675 VANDF
002938 NDDF
2393 RXNORM
373468005 SNOMEDCT_US
d00035 MMSL
386 INN_ID
CHEMBL76 ChEMBL_ID
CHEMBL58510 ChEMBL_ID
CHEMBL1326 ChEMBL_ID
C023676 MESH_SUPPLEMENTAL_RECORD_UI
DB00608 DRUGBANK_ID
CHEMBL1669 ChEMBL_ID
CLQ PDB_CHEM_ID
CHEBI:3638 CHEBI
5535 IUPHAR_LIGAND_ID
2719 PUBCHEM_CID
CHEMBL2095223 ChEMBL_ID
CHEMBL4297165 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 50090-4967 TABLET 250 mg ORAL ANDA 12 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 64980-177 TABLET 250 mg ORAL ANDA 12 sections
Chloroquine Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 64980-178 TABLET 500 mg ORAL ANDA 12 sections
Chloroquine phosphate HUMAN PRESCRIPTION DRUG LABEL 1 76385-142 TABLET, FILM COATED 250 mg ORAL ANDA 13 sections