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

Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1949))
International Nonproprietary Names
INN number INN
386 chloroquine
Aralen® | chloraquine | Malaquin®
Chloroquine is a 4-aminoquinoline and used primarily as 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.
The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 444810 and PubChem CID 639540.
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)
DrugBank Ligand DB00608
GtoPdb PubChem SID 178102177
PubChem CID 2719
Search Google for chemical match using the InChIKey WHTVZRBIWZFKQO-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WHTVZRBIWZFKQO
Search PubMed clinical trials chloroquine
Search PubMed titles chloroquine
Search PubMed titles/abstracts chloroquine
Search UniChem for chemical match using the InChIKey WHTVZRBIWZFKQO-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone WHTVZRBIWZFKQO
Wikipedia Chloroquine