Compound Detail

CHEMBL1535

HYDROXYCHLOROQUINE

💊 Approved Drug

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💊 Approved Drug

CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1535
Name	HYDROXYCHLOROQUINE
Phase	Approved
Structure Type	MOL
InChI Key	XXSMGPRMXLTPCZ-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Hidroxicloroquina Hydroxychloroquine Polirreumin

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

335.9

MW (Da)

3.78

ALogP

HBA

HBD

48.4

PSA (Å²)

0.73

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1955
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula	C18H26ClN3O
MW	335.88
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	-1.23

Indications

Malaria Abortion, Habitual Antiphospholipid Syndrome Arthritis, Rheumatoid Coronavirus Infections Giant Cell Arteritis Graft vs Host Disease Infections Influenza, Human Lupus Erythematosus, Cutaneous Lupus Erythematosus, Systemic Osteoarthritis Pericarditis Pneumonia Pneumonia, Pneumocystis Pneumonia, Viral Polyendocrinopathies, Autoimmune Pre-Eclampsia Pregnancy Respiratory Distress Syndrome

ATC Classification

P01BA02

hydroxychloroquine

Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

Level 2: ANTIPROTOZOALS

Activity Summary

IC50 24 meas. best 9.68

Ki 15 meas. best 6.9

EC50 4 meas. best 6.14

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	9.68	8.0	0.2	2
Plasmodium falciparum CHEMBL364	IC50	7.67	6.66	21.5	2
Toll-like receptor 9 CHEMBL5804	IC50	6.96	6.96	110.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.9	6.9	125.9	1
Unchecked CHEMBL612545	Ki	6.5	6.5	319.0	1
SARS-CoV-2 CHEMBL4303835	IC50	6.17	5.72	676.1	4
SARS-CoV-2 CHEMBL4303835	EC50	6.14	5.7825	720.0	4
Angiotensin-converting enzyme 2 CHEMBL3736	IC50	6.14	6.14	720.0	1
Toll-like receptor 7 CHEMBL5936	IC50	6.1	5.7567	800.0	3
Sigma intracellular receptor 2 CHEMBL4105907	Ki	6.0	6.0	1000.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	5.98	5.635	1049.0	2
Alpha-1D adrenergic receptor CHEMBL223	Ki	5.63	5.63	2346.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	5.6	5.6	2511.9	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	5.53	5.53	2951.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	5.32	5.32	4786.3	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	5.32	5.32	4772.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	5.26	5.26	5495.4	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.19	5.19	6456.5	1
dengue virus type 2 CHEMBL613966	IC50	5.01	5.008	9700.0	5
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	4.81	4.81	15488.2	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	4.8	4.8	15848.9	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	4.7	4.7	19952.6	1
Cyclic GMP-AMP synthase CHEMBL4105728	IC50	4.64	4.64	23000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.48	4.2667	33000.0	3
Alpha-2B adrenergic receptor CHEMBL1942	Ki	4.14	4.14	72443.6	1
Nonstructural protein 3 CHEMBL4523954	Ki	4.04	4.04	92300.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	25325.35	ng.hr.mL-1	Homo sapiens
AUC	34360.52	ng.hr.mL-1	Homo sapiens
AUC	4097.74	ng.hr.mL-1	Homo sapiens
AUC	12662.68	ng.hr.mL-1	Homo sapiens
AUC	18003.17	ng.hr.mL-1	Homo sapiens
AUC	11419.92	ng.hr.mL-1	Homo sapiens
AUC	140.1	-	Chlorocebus sabaeus
CL	11.0	mL.min-1.kg-1	Homo sapiens
Cmax	1220.0	nM	Homo sapiens
Cmax	60.0	nM	Homo sapiens
Cmax	360.0	nM	Homo sapiens
Cmax	7000.0	nM	Homo sapiens
Fu	0.57	-	Homo sapiens
MRT	1300.0	hr	Homo sapiens
T1/2	850.0	hr	Homo sapiens
T1/2	172.3	hr	Homo sapiens
T1/2	549.9	hr	Homo sapiens
T1/2	241.0	hr	Homo sapiens
Tmax	2.4	hr	Homo sapiens
Tmax	6.1	hr	Homo sapiens
Tmax	72.8	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	0.21	nM	9.68	Inhibition of V-ATPase activity in lysosomes of human PC-3 cells	38295689
Plasmodium falciparum	IC50	=	21.5	nM	7.67	Antimalarial activity against chloroquine-resistant Plasmodium falciparum T996 i...	31911292
Toll-like receptor 9	IC50	=	110.0	nM	6.96	Antagonist activity at human TLR9 expressed in HEK-Blue cells assessed as reduct...	30292896
Sigma non-opioid intracellular receptor 1	Ki	=	125.89	nM	6.9	Displacement of [3H]-pentazocin from the Sigma1 receptor	32353859
Unchecked	Ki	=	319.0	nM	6.5	DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan)	-
Unchecked	IC50	=	479.0	nM	6.32	DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan)	-
SARS-CoV-2	IC50	=	676.08	nM	6.17	IC50 for antiviral activity against SARS-CoV-2 in the Vero E6 cell line at 48 h ...	32353859
SARS-CoV-2	EC50	=	720.0	nM	6.14	Antiviral activity against SARS-CoV-2 infected in Vero E6 cells assessed as redu...	33486200
SARS-CoV-2	IC50	=	720.0	nM	6.14	Antiviral activity against SARS-CoV-2 assessed as inhibition of viral growth	36966652
SARS-CoV-2	EC50	=	720.0	nM	6.14	Antiviral activity against Severe acute respiratory syndrome coronavirus 2 infec...	32771797
SARS-CoV-2	IC50	=	720.0	nM	6.14	Antiviral activity against SARS-CoV-2 infected in African green monkey Vero cell...	32845145
Angiotensin-converting enzyme 2	IC50	=	720.0	nM	6.14	Inhibition of human recombinant ACE2 at 50 uM using (7Mca-Y-V-A- D -A-P- K(Knp) ...	32539378
Toll-like receptor 7	IC50	=	800.0	nM	6.1	Antagonist activity at human TLR7 expressed in HEK-Blue cells assessed as reduct...	30292896
Toll-like receptor 7	IC50	=	800.0	nM	6.1	Antagonist activity at TLR7 (unknown origin)	33189437
Sigma intracellular receptor 2	Ki	=	1000.0	nM	6.0	Displacement of [3H]-DTG from the Sigma2 receptor	32353859
Muscarinic acetylcholine receptor M2	Ki	=	1049.0	nM	5.98	DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
SARS-CoV-2	EC50	=	1740.0	nM	5.76	Antiviral activity against SARS-CoV-2 UC-1075 infected in African green monkey V...	33479570
Plasmodium falciparum	IC50	=	2217.0	nM	5.65	Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 inf...	31911292
Alpha-1D adrenergic receptor	Ki	=	2346.0	nM	5.63	DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin)	-
Voltage-gated inwardly rectifying potassium channel KCNH2	Ki	=	2511.89	nM	5.6	hERG binding assays: Displacement of [3H]-Dofetilide (5 nM final) from hERG memb...	32353859

Literature References

PubMed	DOI	Target Context	# Activities
19188392	10.1128/aac.00339-08	Homo sapiens	19
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
25699157	10.1021/ml500348p	NCI-H460	5
28570977	10.1016/j.ejmech.2017.05.050	A549	5
18426954	10.1124/dmd.108.020479	ADMET	4
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
26771861	10.1021/acs.jmedchem.5b01653	dengue virus type 2	4
32353859	10.1038/s41586-020-2286-9	SARS-CoV-2	3
25699157	10.1021/ml500348p	NON-PROTEIN TARGET	3
32353859	10.1038/s41586-020-2286-9	Vero C1008	2
32353859	10.1038/s41586-020-2286-9	ADMET	2
31550663	10.1016/j.ejmech.2019.111715	Polycomb protein EED	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
26948801	10.1016/j.drudis.2016.02.015	Homo sapiens	2
33479570	10.1021/acsmedchemlett.0c00485	Vero	2
31911292	10.1016/j.ejmech.2019.111983	Plasmodium falciparum	2
33479570	10.1021/acsmedchemlett.0c00485	SARS-CoV-2	2
-	10.6019/CHEMBL4651402	Vero C1008	2

Data from ChEMBL 36 via Core Engine