Hydroxychloroquine (CHEM002518)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-07-30 17:58:56 UTC
Update Date2016-11-09 01:08:52 UTC
Accession NumberCHEM002518
Identification
Common NameHydroxychloroquine
ClassSmall Molecule
DescriptionHydroxychloroquine is only found in individuals that have used or taken this drug. It is a chemotherapeutic agent that acts against erythrocytic forms of malarial parasites. Although the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antimalarial
  • Antirheumatic Agent
  • Dermatologic Agent
  • Drug
  • Enzyme Inhibitor
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-HydroxychloroquineChEBI
2-((4-((7-Chloro-4-quinolyl)amino)pentyl)ethylamino)ethanolChEBI
2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanolChEBI
7-Chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinolineChEBI
7-Chloro-4-(4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinolineChEBI
7-Chloro-4-[4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinolineChEBI
7-Chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinolineChEBI
HidroxicloroquinaChEBI
HydroxychloroquinumChEBI
NSC4375ChEBI
OxichlorochineChEBI
OxichloroquineChEBI
PolirreuminChEBI
7-Chloro-4-(4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino)quinolineGenerator
7-Chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)quinolineGenerator
7-Chloro-4-[4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino]quinolineGenerator
7-Chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinolineGenerator
HCQHMDB
OxychlorochinHMDB
Hydroxychloroquine sulfate (1:1) saltHMDB
OxychloroquineHMDB
HydroxychlorochinHMDB
Hydroxychloroquine sulfateHMDB
PlaquenilHMDB
Chemical FormulaC18H26ClN3O
Average Molecular Mass335.872 g/mol
Monoisotopic Mass335.176 g/mol
CAS Registry Number118-42-3
IUPAC Name2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
Traditional Namehydroxychloroquine
SMILESCCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1
InChI IdentifierInChI=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)
InChI KeyXXSMGPRMXLTPCZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct Parent4-aminoquinolines
Alternative Parents
Substituents
  • Chloroquinoline
  • 4-aminoquinoline
  • Haloquinoline
  • Aminopyridine
  • Secondary aliphatic/aromatic amine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Secondary amine
  • Azacycle
  • Alkanolamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point89-91°C
Boiling PointNot Available
Solubility2.61e-02 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP3.87ALOGPS
logP2.89ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.39 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity97.97 m³·mol⁻¹ChemAxon
Polarizability38.3 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-9262000000-58dde1657b5d6098be9bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9266000000-ea4f93631dd2ecfd327cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-0970000000-727b5fa0ccae5ed8e353Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004l-0920000000-7ac7ca483022df09c0afSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-4ef780743e3f6b698679Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000j-0179000000-2cc295a00cfa8b906a76Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-0970000000-7083c4ae0b9ffd9bdd65Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0390000000-5a80b772bbcf76126d36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-3ad87c8e6d06353b69a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-069a-3849000000-89ef84bf56d7c636c87aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054n-9460000000-09312fdaefa09ffd4066Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-7d2e379f85931a4c8042Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1229000000-f952822a37d6efa233afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9641000000-8b6d466c2c58b3345281Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0039000000-ef94af670ab631c9aa96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0094000000-a09f3e2ffce0834eeb4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-6960000000-4349c6d77ff753227523Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-e3a3afc02d61a6461805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fsl-0129000000-7fba6200eea5e933699fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1940000000-c48ff4523d2ef3631ba7Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f6t-3972000000-7c193125680c0c9e276fSpectrum
Toxicity Profile
Route of ExposureVery rapidly and completely absorbed following oral administration.
Mechanism of ToxicityAlthough the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown.
MetabolismPartially hepatic, to active de-ethylated metabolites. Half Life: Terminal elimination half-life In blood is approximately 50 days. In plasma it is approximately 32 days.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the suppressive treatment and treatment of acute attacks of malaria due to Plasmodium vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include headache, drowsiness, visual disturbances, cardiovascular collapse, and convulsions, followed by sudden and early respiratory and cardiac arrest. The electrocardiogram may reveal atrial standstill, nodal rhythm, prolonged intraventricular conduction time, and progressive bradycardia leading to ventricular fibrillation and/or arrest.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01611
HMDB IDHMDB0015549
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHydroxychloroquine
Chemspider ID3526
ChEBI ID5801
PubChem Compound ID3652
Kegg Compound IDC07043
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

U.S. Patent 2,546,658.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23216212
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23218706
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23481418
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23485647
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23581274
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23778483
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23887202
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23902281