Human Metabolome Database Version 3.5

Showing metabocard for Hydroxychloroquine (HMDB15549)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:52 -0600
Update Date 2013-02-08 17:33:58 -0700
HMDB ID HMDB15549
Secondary Accession Numbers None
Metabolite Identification
Common Name Hydroxychloroquine
Description Hydroxychloroquine 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.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. HCQ
Chemical Formula C18H26ClN3O
Average Molecular Weight 335.872
Monoisotopic Molecular Weight 335.176440176
IUPAC Name 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
Traditional IUPAC Name hydroxychloroquine
CAS Registry Number 118-42-3
SMILES CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1
InChI Identifier 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)
InChI Key XXSMGPRMXLTPCZ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Quinolines and Derivatives
Sub Class Aminoquinolines and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Aminopyridine
  • Aryl Chloride
  • Chlorobenzene
  • Organochloride
  • Polyamine
  • Primary Alcohol
  • Pyridine
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Aminoquinolines and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Antimalarials
  • Antiprotozoal Agents
  • Antirheumatic Agents
  • Dermatologic Agents
  • Enzyme Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 90 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2.61e-02 g/L Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.026 g/L ALOGPS
LogP 3.87 ALOGPS
LogP 2.89 ChemAxon
LogS -4.11 ALOGPS
pKa (strongest acidic) 15.59 ChemAxon
pKa (strongest basic) 9.76 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 48.39 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 97.97 ChemAxon
Polarizability 38.3 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01611
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01611
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01611 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 3526 Link_out
KEGG Compound ID C07043 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Hydroxychloroquine Link_out
NuGOwiki Link HMDB15549 Link_out
Metagene Link HMDB15549 Link_out
METLIN ID Not Available
PubChem Compound 3652 Link_out
PDB ID Not Available
ChEBI ID 529737 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Toll-like receptor 9
Reactions: Not Available
Gene Name: TLR9
Uniprot ID: Q9NR96 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA