HYDROXYCHLOROQUINE

Search structure
Synonyms:
Status: Approved (1955)
Entry Type: Small molecule
Molecule Category: Parent
ATC: P01BA02
UNII: 4QWG6N8QKH

Structure
InChI Key XXSMGPRMXLTPCZ-UHFFFAOYSA-N
Smile 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

Pharmacology

Primary Target
TLR7
TLR9
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Toll-like and Il-1 receptors
- 800-8600 - - -
Unclassified protein
- - - 92300 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Osteoarthritis 3 D010003 ClinicalTrials
Coronavirus Infections 3 D018352 ClinicalTrials
Arthritis, Rheumatoid 3 D001172 ClinicalTrials
Antiphospholipid Syndrome 3 D016736 ClinicalTrials
Lupus Erythematosus, Systemic 3 D008180 ClinicalTrials
Pregnancy 3 D011247 ClinicalTrials
Lupus Erythematosus, Cutaneous 3 D008178 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Sjogren's Syndrome 3 D012859 ClinicalTrials
Pneumonia 3 D011014 ClinicalTrials
Sarcoidosis, Pulmonary 3 D017565 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Respiratory Insufficiency 3 D012131 ClinicalTrials
Abortion, Habitual 3 D000026 ClinicalTrials
Giant Cell Arteritis 3 D013700 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Thrombocytopenia 3 D013921 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Respiratory Distress Syndrome 3 D012128 ClinicalTrials
Respiratory Distress Syndrome 3 D012128 ClinicalTrials
Pneumonia, Pneumocystis 3 D011020 ClinicalTrials
Pneumonia, Viral 3 D011024 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Carcinoma, Hepatocellular 2 D006528 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Crohn Disease 2 D003424 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Small Cell Lung Carcinoma 2 D055752 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Diabetes Mellitus, Type 1 2 D003922 ClinicalTrials
Diabetes Mellitus, Type 2 2 D003924 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Multiple Sclerosis, Chronic Progressive 2 D020528 ClinicalTrials
Osteoarthritis, Knee 2 D020370 ClinicalTrials
Lichen Planus 2 D008010 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Porphyria Cutanea Tarda 2 D017119 ClinicalTrials
Zellweger Syndrome 2 D015211 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Cholangiocarcinoma 2 D018281 ClinicalTrials
Adenocarcinoma 1 D000230 ClinicalTrials
Hidradenitis Suppurativa 1 D017497 ClinicalTrials
Hepatitis C, Chronic 1 D019698 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Insulin Resistance 1 D007333 ClinicalTrials
Osteosarcoma 1 D012516 ClinicalTrials
Lymphangioleiomyomatosis 1 D018192 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Central Nervous System Neoplasms 1 D016543 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Glioma 1 D005910 ClinicalTrials
Ovarian Neoplasms 1 D010051 ClinicalTrials
Retinitis Pigmentosa 1 D012174 ClinicalTrials
Lung Neoplasms 1 D008175 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Cystic Fibrosis 1 D003550 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials
Prostatic Neoplasms 0 D011471 ClinicalTrials
Lung Diseases, Interstitial 0 D017563 ClinicalTrials

Related Entries

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 118-42-3
ChEBI 5801
ChEMBL CHEMBL1535
DrugBank DB01611
DrugCentral 1395
EPA CompTox DTXSID8023135
FDA SRS 4QWG6N8QKH
Human Metabolome Database HMDB0015549
Guide to Pharmacology 7198
KEGG C07043
PharmGKB PA164777036
PubChem 3652
SureChEMBL SCHEMBL8170
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