chloroquine

Ligand id: 5535

Name: chloroquine

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 28.16
Molecular weight 319.18
XLogP 4.15
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1949))
IUPAC Name
N'-(7-chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine
International Nonproprietary Names
INN number INN
386 chloroquine
Synonyms
Aralen® | chloraquine | Malaquin®
Comments
Chloroquine is primarily an antimalarial drug. In humans chloroquine inhibits thiamine uptake acting specifically on thiamine transporter 2 (SLC19A3). Other uses of chloroquine include treatment of autoimmune disorders (rheumatoid arthritis and lupus erythematosus), as an antiretroviral (HIV-1/AIDS and chikungunya fever) and as a radiosensitizing/chemosensitizing agent benefitting cancer therapies.
Marketed formulations may contain chloroquine phosphate (PubChem CID 64927).
Chloroquine is one of the antimalarials listed in the WHO 20th Essential Medicines List (2017).
Database Links
BitterDB Ligand 87
CAS Registry No. 54-05-7 (source: Scifinder)
ChEBI CHEBI:3638
ChEMBL Ligand CHEMBL76
DrugBank Ligand DB00608
GtoPdb PubChem SID 178102177
PubChem CID 2719
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Wikipedia Chloroquine