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Substance Name: Hydroxychloroquine [INN:BAN]
RN: 118-42-3
UNII: 4QWG6N8QKH
InChIKey: XXSMGPRMXLTPCZ-UHFFFAOYSA-N

Note

  • 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 Formula

  • C18-H26-Cl-N3-O

Molecular Weight

  • 335.8764
 

Classification Codes

  • Anti-Infective Agents
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data

Names and Synonyms

Name of Substance

  • Hydroxychloroquine
  • Hydroxychloroquine [INN:BAN]

MeSH Heading

  • Hydroxychloroquine

Synonyms

  • 2-((4-((7-Chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol
  • 2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol
  • 5-22-10-00280 (Beilstein Handbook Reference)
  • 7-Chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline
  • 7-Chloro-4-(4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline
  • 7-Chloro-4-(5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl)aminoquinoline
  • BRN 0253894
  • EINECS 204-249-8
  • Hidroxicloroquina
  • Hidroxicloroquina [INN-Spanish]
  • Hydroxychloroquine
  • Hydroxychloroquinum
  • Hydroxychloroquinum [INN-Latin]
  • Idrossiclorochina
  • Idrossiclorochina [DCIT]
  • Oxichlorochinum
  • Plaquenil
  • UNII-4QWG6N8QKH
  • WIN 1258
  • Z0188

Systematic Names

  • Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethylamino)-
  • Ethanol, 2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)-
  • Hydroxychloroquine

Registry Numbers

CAS Registry Number

  • 118-42-3

FDA UNII

  • 4QWG6N8QKH

Related Registry Number

  • 747-36-4 (sulfate (1:1) salt)

System Generated Number

  • 0000118423

Structure Descriptors

InChI

1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)

InChIKey

XXSMGPRMXLTPCZ-UHFFFAOYSA-N

Smiles

CCN(CCCC(C)Nc1ccnc2c1ccc(c2)Cl)CCO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 600mg/kg (600mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES
Journal of Analytical Toxicology. Vol. 14, Pg. 186, 1990.
human TDLo oral 429mg/kg/25D (429mg/kg) BLOOD: AGRANULOCYTOSIS

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Lancet. Vol. 1, Pg. 1275, 1965.
man TDLo oral 154mg/kg/18D- (154mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Journal of the American Academy of Dermatology. Vol. 12, Pg. 863, 1985.
mouse LD50 oral 1240mg/kg (1240mg/kg)   Journal of Medicinal Chemistry. Vol. 12, Pg. 184, 1969.
women TDLo oral 88mg/kg/11D-I (88mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Journal of the American Academy of Dermatology. Vol. 12, Pg. 857, 1985.
women TDLo oral 112mg/kg/2W-I (112mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE" Journal of Rheumatology. Vol. 12, Pg. 391, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 90 deg C   EXP
log P (octanol-water) 3.030 (none)   EST
Atmospheric OH Rate Constant 1.65E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.