Hydroxychloroquine

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 accumliates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown. Structure

Synonyms

Value Source (+-)-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 OxychlorochinMeSH Hydroxychloroquine slifate (1:1) saltMeSH OxychloroquineMeSH HydroxychlorochinMeSH Hydroxychloroquine slifateMeSH PlaquenilMeSH

Chemical Formlia

C₁₈H₂₆ClN₃O Average Molecliar Weight

335.872 Monoisotopic Molecliar Weight

335.176440176 IUPAC Name

2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol Traditional Name

hydroxychloroquine CAS Registry Number

118-42-3 SMILES

InChI Identifier

InChI Key

XXSMGPRMXLTPCZ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound 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. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Quinolines and derivatives Sub Class

Aminoquinolines and derivatives Direct Parent

4-aminoquinolines Alternative Parents

Chloroquinolines

Secondary alkylarylamines

Aminopyridines and derivatives

Benzenoids

Aryl chlorides

Heteroaromatic compounds

Trialkylamines

1,2-aminoalcohols

Azacyclic compounds

Primary alcohols

Organopnictogen compounds

Organochlorides

Hydrocarbon derivatives

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

Molecliar Framework

Aromatic heteropolycyclic compounds External Descriptors

tertiary amino compound (CHEBI:5801 )

organochlorine compound (CHEBI:5801 )

secondary amino compound (CHEBI:5801 )

primary alcohol (CHEBI:5801 )

aminoquinoline (CHEBI:5801 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Antimalarials

Antiprotozoal Agents

Antirheumatic Agents

Dermatologic Agents

Enzyme Inhibitors

Application

Pharmaceutical

Cellliar locations

Cytoplasm

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point90 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.61e-02 g/LNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility0.026 mg/mLALOGPS 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

Mass Spectrum (Electron Ionization)splash10-0f6t-3972000000-7c193125680c0c9e276fView in MoNA

Biological Properties Cellliar Locations

Cytoplasm

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01611

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01611

21059682

details

Abnormal Concentrations

Not Available Predicted Concentrations

Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01611 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 KEGG Compound ID

C07043 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Hydroxychloroquine NuGOwiki Link

HMDB15549 Metagene Link

HMDB15549 METLIN ID

Not Available PubChem Compound

3652 PDB ID

Not Available ChEBI ID

529737

Product: Amifampridine

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not 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 ]

PMID: 21851806

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