HYDROXYCHLOROQUINE

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Synonyms
Status
Molecule Category Free-form
ATC P01BA02
UNII 4QWG6N8QKH
EPA CompTox DTXSID8023135

Structure

InChI Key XXSMGPRMXLTPCZ-UHFFFAOYSA-N
Smiles CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H26ClN3O
Molecular Weight 335.88
AlogP 3.78
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 9.0
Polar Surface Area 48.39
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 23.0
Assay Description Organism Bioactivity Reference
DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) Rattus norvegicus 479.0 nM DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) Rattus norvegicus 319.0 nM
Antagonist activity at human TLR9 expressed in HEK-Blue cells assessed as reduction in CpGB-induced NF-kappaB levels after 24 hrs by spectrophotometric analysis Homo sapiens 110.0 nM
Antagonist activity at human TLR7 expressed in HEK-Blue cells assessed as reduction in CL264-induced NF-kappaB levels after 24 hrs by spectrophotometric analysis Homo sapiens 800.0 nM
IC50 for antiviral activity against SARS-CoV-2 in the Vero E6 cell line at 48 h by immunofluorescence-based assay (detecting the viral NP protein in the nucleus of the Vero E6 cells). Chlorocebus sabaeus 676.08 nM
Displacement of [3H]-pentazocin from the Sigma1 receptor Homo sapiens 125.89 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.33 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.06 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.06 %
Antimalarial activity against chloroquine-resistant Plasmodium falciparum T996 infected in human erythrocytes assessed as inhibition of [G-3H]hypoxanthine uptake preincubated for 24 hrs followed by [G-3H]hypoxanthine addition and measured after 18 to 24 hrs by scintillation spectrometry Plasmodium falciparum 21.5 nM
Antiviral activity against SARS-CoV-2 infected in African green monkey Vero cells incubated for 48 hrs by RT-PCR method Severe acute respiratory syndrome coronavirus 2 720.0 nM
Antagonist activity at TLR7 (unknown origin) Homo sapiens 800.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 5801
ChEMBL CHEMBL1535
DrugBank DB01611
DrugCentral 1395
FDA SRS 4QWG6N8QKH
Human Metabolome Database HMDB0015549
Guide to Pharmacology 7198
KEGG C07043
PharmGKB PA164777036
PubChem 3652
SureChEMBL SCHEMBL8170
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