hydroxychloroquine indications/contra

Stem definitionDrug idCAS RN
quinoline derivatives 1395 118-42-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • hydroxychloroquine
  • hydroxychloroquine sulfate
  • oxichloroquine
  • oxychlorochin
  • oxychloroquine
A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites. Hydroxychloroquine appears to concentrate in food vacuoles of affected protozoa. It inhibits plasmodial heme polymerase. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p970)
  • Molecular weight: 335.88
  • Formula: C18H26ClN3O
  • CLOGP: 4.12
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 48.39
  • ALOGS: -4.11
  • ROTB: 9

Drug dosage:

DoseUnitRoute
0.52 g O

Approvals:

DateAgencyCompanyOrphan
April 18, 1955 FDA SANOFI AVENTIS US

FDA Adverse Event Reporting System

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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 ineffective 5965.17 29.42 1806 3962 114284 3265807
Rheumatoid arthritis 4556.14 29.42 988 4780 14650 3365441
Drug intolerance 2469.77 29.42 573 5195 11225 3368866
Joint swelling 1818.95 29.42 483 5285 16574 3363517
Treatment failure 1683.47 29.42 377 5391 6147 3373944
Synovitis 1562.72 29.42 287 5481 1558 3378533
Pain 1145.79 29.42 485 5283 71072 3309019
Arthralgia 1061.80 29.42 439 5329 60422 3319669
Drug hypersensitivity 1012.03 29.42 367 5401 35313 3344778
Condition aggravated 996.43 29.42 372 5396 38861 3341230
Nausea 871.11 29.42 485 5283 129160 3250931
Drug effect incomplete 717.95 29.42 198 5570 7652 3372439
Abdominal discomfort 708.90 29.42 240 5528 18644 3361447
Peripheral swelling 697.00 29.42 228 5540 15904 3364187
Fatigue 651.98 29.42 377 5391 106863 3273228
Arthropathy 574.59 29.42 166 5602 7585 3372506
Drug effect decreased 556.40 29.42 179 5589 11790 3368301
Rash 549.48 29.42 293 5475 70528 3309563
Loss of personal independence in daily activities 547.03 29.42 147 5621 5123 3374968
C-reactive protein abnormal 496.73 29.42 85 5683 275 3379816
Diarrhoea 473.70 29.42 305 5463 104043 3276048
Red blood cell sedimentation rate abnormal 442.87 29.42 72 5696 152 3379939
Swelling 442.46 29.42 170 5598 18874 3361217
Systemic lupus erythematosus 441.82 29.42 114 5654 3374 3376717
Musculoskeletal stiffness 436.31 29.42 155 5613 13795 3366296
Alopecia 425.08 29.42 165 5603 18821 3361270
C-reactive protein increased 409.93 29.42 134 5634 9249 3370842
Vomiting 384.13 29.42 253 5515 89278 3290813
Headache 382.75 29.42 255 5513 91725 3288366
Mobility decreased 378.41 29.42 128 5640 9820 3370271

Pharmacologic Action:

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SourceCodeDescription
ATC P01BA02 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Aminoquinolines
FDA EPC N0000175713 Antirheumatic Agent
CHEBI has role CHEBI:35842 antirheumatic drug
CHEBI has role CHEBI:50177 dermatologic drug
CHEBI has role CHEBI:38068 antimalarial
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D004791 Enzyme Inhibitors

Drug Use (View source of the data)

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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 Ovale Malaria Prevention indication
Malaria Prevention indication
Plasmodium Falciparum Malaria Prevention indication
Plasmodium Malariae Malaria Prevention indication
Alcoholism contraindication 7200002
Psoriasis contraindication 9014002 DOID:8893
Visual field defect contraindication 12184005
Retinal disorder contraindication 29555009 DOID:5679
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
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 DOID:13268
Vasculitis of the skin off-label use 53312001
Porphyria cutanea tarda off-label use 61860000 DOID:3132
Q fever endocarditis off-label use 95890006
Polymorphic light eruption off-label use 238525001
Juvenile rheumatoid arthritis off-label use 410795001
Hypercalcemia associated with Sarcoidosis off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.51 Basic
pKa2 7.83 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Toll-like receptor 7 Membrane receptor ANTAGONIST IC50 5.56 IUPHAR CHEMBL
Toll-like receptor 9 Membrane receptor ANTAGONIST IC50 7.10 IUPHAR CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 5.98 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.63 DRUG MATRIX
Hemoglobin subunit alpha Secreted WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel WOMBAT-PK

External reference:

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IDSource
4019780 VUID
N0000147871 NUI
C0020336 UMLSCUI
7198 IUPHAR_LIGAND_ID
D02114 KEGG_DRUG
4QWG6N8QKH UNII
796 INN_ID
5521 RXNORM
373540008 SNOMEDCT_US
83490000 SNOMEDCT_US
4852 MMSL
d00817 MMSL
4019780 VANDF
N0000147871 NDFRT
N0000006573 NDFRT
004906 NDDF
747-36-4 SECONDARY_CAS_RN
CHEMBL1535 ChEMBL_ID
3652 PUBCHEM_CID
CHEMBL1690 ChEMBL_ID
D006886 MESH_DESCRIPTOR_UI
DB01611 DRUGBANK_ID
CHEBI:5801 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0143-2128 TABLET, FILM COATED 200 mg ORAL ANDA 10 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0378-0373 TABLET, FILM COATED 200 mg ENTERAL ANDA 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0591-3041 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0781-1407 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6508 TABLET, FILM COATED 200 mg ORAL ANDA 12 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 10544-578 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 16714-474 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 16714-753 TABLET, FILM COATED 200 mg ORAL ANDA 12 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 21695-486 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 33261-933 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 42291-318 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Plaquenil HUMAN PRESCRIPTION DRUG LABEL 1 42291-335 TABLET 200 mg ORAL NDA 12 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 42292-011 TABLET, FILM COATED 200 mg ENTERAL ANDA 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 43353-051 TABLET 200 mg ORAL NDA AUTHORIZED GENERIC 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 43353-103 TABLET, FILM COATED 200 mg ORAL ANDA 10 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 43353-794 TABLET 200 mg ORAL ANDA 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 43353-972 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Plaquenil HUMAN PRESCRIPTION DRUG LABEL 1 43353-997 TABLET 200 mg ORAL NDA 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 50090-0681 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 50090-2508 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 51660-296 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 54868-3821 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Hydroxychloroquine sulfate HUMAN PRESCRIPTION DRUG LABEL 1 55154-2074 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Plaquenil HUMAN PRESCRIPTION DRUG LABEL 1 59212-562 TABLET 200 mg ORAL NDA 15 sections
HYDROXYCHLOROQUINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 61919-132 TABLET, FILM COATED 200 mg ORAL ANDA 10 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 63304-296 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Hydroxychloroquine sulfate HUMAN PRESCRIPTION DRUG LABEL 1 63739-777 TABLET, FILM COATED 200 mg ORAL ANDA 12 sections
Hydroxychloroquine sulfate HUMAN PRESCRIPTION DRUG LABEL 1 65841-633 TABLET, FILM COATED 200 mg ORAL ANDA 12 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 66336-555 TABLET, FILM COATED 200 mg ORAL ANDA 13 sections
Hydroxychloroquine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 66993-057 TABLET 200 mg ORAL NDA AUTHORIZED GENERIC 11 sections