HYDROXYCHLOROQUINE SULFATE

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Search structure


Trade Names	HYDROXYCHLOROQUINE SULFATE PLAQUENIL
Synonyms	Ercoquin Hydroxychloroquine Sulfate Hydroxychloroquine sulfate Hydroxychloroquine sulphate NSC-4375 Oxichlorochine Oxichlorochine sulfate Oxiklorin Plaquenil Quensyl Quinoric TCMDC-123987
Status
Molecule Category	Salt-form
UNII	8Q2869CNVH
EPA CompTox	DTXSID1047811
Parent Compound:	HYDROXYCHLOROQUINE


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	JCBIVZZPXRZKTI-UHFFFAOYSA-N
Smiles	CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12.O=S(=O)(O)O
InChI	InChI=1S/C18H26ClN3O.H2O4S/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;1-5(2,3)4/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21);(H2,1,2,3,4)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H28ClN3O5S
Molecular Weight	433.96
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

Bioactivity

Mechanism of Action	Action	Reference
Ferriprotoporphyrin IX inhibitor	INHIBITOR	PubMed Wikipedia


Protein: Toll-like receptor 9 Description: Toll-like receptor 9 Organism : Homo sapiens Q9NR96 ENSG00000239732






Protein: Toll-like receptor 7 Description: Toll-like receptor 7 Organism : Homo sapiens Q9NYK1 ENSG00000196664

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	90

Assay Description	Organism	Bioactivity	Reference
GSK_TCMDC: Inhibition of Plasmodium falciparum 3D7 in whole red blood cells, using parasite LDH activity as an index of growth. Test compounds present at 2uM	Plasmodium falciparum	99.0 %
GSK_TCMDC: Inhibition of Plasmodium falciparum Dd2 in whole red blood cells, using parasite LDH activity as an index of growth. Test compounds present at 2uM	Plasmodium falciparum	0.0 %
GSK_TCMDC: Inhibition of Plasmodium falciparum 3D7 LDH activity, using an LDH reporter assay. Test compounds present at 2uM	Plasmodium falciparum	0.0 %
GSK_TCMDC: Percent inhibition of human HepG2 cell line. Test compounds present at 10uM.	Homo sapiens	3.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	90.44 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	90.84 %
ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmGLUT1 that are glucose transport deficient and complemented with the human glucose transporter GLUT1. Activity is measured by DNA content using SYBR green in vitro	Leishmania mexicana	7.0 %
ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmPfHT that are glucose transport deficient and complemented with the Plasmodium falciparum hexose transporter. Activity is measured by by DNA content using SYBR green in vitro	Leishmania mexicana	7.44 %
ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmGT2 that are glucose transport deficient and complemented with the L. Mexicana glucose transporter 2. Activity is measured by by DNA content using SYBR green in vitro	Leishmania mexicana	6.05 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	3.2 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	13.04 %
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 %

Cross References

Resources	Reference
ChEMBL	CHEMBL1690
FDA SRS	8Q2869CNVH
PubChem	12947
SureChEMBL	SCHEMBL41114

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).