Ligand id: 7198

Name: hydroxychloroquine

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Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 48.39
Molecular weight 335.18
XLogP 3.14
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 (1955))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
International Nonproprietary Names
INN number INN
796 hydroxychloroquine
Dolquine® | Plaquenil®
Hydroxychloroquine is a 4-aminoquinoline and used primarily as an antimalarial drug.
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 178395 and PubChem CID 178396.
The marketed formulations contain hydroxychloroquine sulfate (PubChem CID 3044369).

Activity at non-malarial protein targets:
Although this drug has direct effects on survival of the malaria parasite it also appears to be an antagonist of two of the human TOLL-like receptors (TLR7 and TLR9). Antagonism of these receptors is likely related to the anti-inflammatory action of this drug in some auto-immune diseases.
Database Links
CAS Registry No. 118-42-3
ChEMBL Ligand CHEMBL1535
DrugBank Ligand DB01611
GtoPdb PubChem SID 178103773
PubChem CID 3652
Search Google for chemical match using the InChIKey XXSMGPRMXLTPCZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XXSMGPRMXLTPCZ
Search PubMed clinical trials hydroxychloroquine
Search PubMed titles hydroxychloroquine
Search PubMed titles/abstracts hydroxychloroquine
Search UniChem for chemical match using the InChIKey XXSMGPRMXLTPCZ-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone XXSMGPRMXLTPCZ
Wikipedia Hydroxychloroquine