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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015549
Secondary Accession Numbers
  • HMDB15549
Metabolite Identification
Common NameHydroxychloroquine
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.
Structure
Data?1582753309
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 Weight335.872
Monoisotopic Molecular Weight335.176440176
IUPAC Name2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
Traditional Namehydroxychloroquine
CAS Registry Number118-42-3
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 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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.026 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM180.230932474
[M+H]+Not Available178.427http://allccs.zhulab.cn/database/detail?ID=AllCCS00000934
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+180.4530932474
DeepCCS[M-H]-178.09230932474
DeepCCS[M-2H]-210.97730932474
DeepCCS[M+Na]+186.54730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HydroxychloroquineCCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C13812.3Standard polar33892256
HydroxychloroquineCCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C12862.3Standard non polar33892256
HydroxychloroquineCCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C12896.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxychloroquine,1TMS,isomer #1CCN(CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12)CCO[Si](C)(C)C2784.9Semi standard non polar33892256
Hydroxychloroquine,1TMS,isomer #2CCN(CCO)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C2703.6Semi standard non polar33892256
Hydroxychloroquine,2TMS,isomer #1CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C)CCO[Si](C)(C)C2715.5Semi standard non polar33892256
Hydroxychloroquine,2TMS,isomer #1CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C)CCO[Si](C)(C)C2740.5Standard non polar33892256
Hydroxychloroquine,2TMS,isomer #1CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C)CCO[Si](C)(C)C3242.2Standard polar33892256
Hydroxychloroquine,1TBDMS,isomer #1CCN(CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12)CCO[Si](C)(C)C(C)(C)C3010.8Semi standard non polar33892256
Hydroxychloroquine,1TBDMS,isomer #2CCN(CCO)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C2946.8Semi standard non polar33892256
Hydroxychloroquine,2TBDMS,isomer #1CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C3130.1Semi standard non polar33892256
Hydroxychloroquine,2TBDMS,isomer #1CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C3120.3Standard non polar33892256
Hydroxychloroquine,2TBDMS,isomer #1CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C3379.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxychloroquine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-9262000000-58dde1657b5d6098be9b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxychloroquine GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9266000000-ea4f93631dd2ecfd327c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxychloroquine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f6t-3972000000-7c193125680c0c9e276f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxychloroquine 40V, Positive-QTOFsplash10-0002-0970000000-727b5fa0ccae5ed8e3532021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxychloroquine 50V, Positive-QTOFsplash10-004l-0920000000-7ac7ca483022df09c0af2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxychloroquine 10V, Positive-QTOFsplash10-000i-0009000000-4ef780743e3f6b6986792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxychloroquine 20V, Positive-QTOFsplash10-000j-0179000000-2cc295a00cfa8b906a762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxychloroquine 40V, Positive-QTOFsplash10-0002-0970000000-7083c4ae0b9ffd9bdd652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxychloroquine 30V, Positive-QTOFsplash10-0002-0390000000-5a80b772bbcf76126d362021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 10V, Positive-QTOFsplash10-000i-0009000000-3ad87c8e6d06353b69a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 20V, Positive-QTOFsplash10-069a-3849000000-89ef84bf56d7c636c87a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 40V, Positive-QTOFsplash10-054n-9460000000-09312fdaefa09ffd40662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 10V, Negative-QTOFsplash10-001i-0009000000-7d2e379f85931a4c80422016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 20V, Negative-QTOFsplash10-001i-1229000000-f952822a37d6efa233af2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 40V, Negative-QTOFsplash10-002f-9641000000-8b6d466c2c58b33452812016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 10V, Positive-QTOFsplash10-000i-0039000000-ef94af670ab631c9aa962021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 20V, Positive-QTOFsplash10-000b-0094000000-a09f3e2ffce0834eeb4d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 40V, Positive-QTOFsplash10-004i-6960000000-4349c6d77ff7532275232021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 10V, Negative-QTOFsplash10-001i-0019000000-e3a3afc02d61a64618052021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 20V, Negative-QTOFsplash10-0fsl-0129000000-7fba6200eea5e933699f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxychloroquine 40V, Negative-QTOFsplash10-004i-1940000000-c48ff4523d2ef3631ba72021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01611 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01611 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01611
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3526
KEGG Compound IDC07043
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydroxychloroquine
METLIN IDNot Available
PubChem Compound3652
PDB IDNot Available
ChEBI ID5801
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Somer M, Kallio J, Pesonen U, Pyykko K, Huupponen R, Scheinin M: Influence of hydroxychloroquine on the bioavailability of oral metoprolol. Br J Clin Pharmacol. 2000 Jun;49(6):549-54. [PubMed:10848718 ]
General function:
Involved in protein binding
Specific function:
Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific of microorganisms. TLR9 is a nucleotide-sensing TLR which is activated by unmethylated cytidine-phosphate-guanosine (CpG) dinucleotides. Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response
Gene Name:
TLR9
Uniprot ID:
Q9NR96
Molecular weight:
115858.7
References
  1. Sun S, Rao NL, Venable J, Thurmond R, Karlsson L: TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35. [PubMed:18220957 ]
  2. Trevani AS, Chorny A, Salamone G, Vermeulen M, Gamberale R, Schettini J, Raiden S, Geffner J: Bacterial DNA activates human neutrophils by a CpG-independent pathway. Eur J Immunol. 2003 Nov;33(11):3164-74. [PubMed:14579285 ]