mepacrine   Click here for help

GtoPdb Ligand ID: 10172

Synonyms: Atabrine® | quinacrine
PDB Ligand Immunopharmacology Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: Mepacrine is an acridine derivative with antiprotozoal activity. Historically used as an antimalarial drug it is now used off-license as an immunomodulatory agent.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 37.39
Molecular weight 399.21
XLogP 5.54
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES CCN(CCCC(Nc1c2cc(OC)ccc2nc2c1ccc(c2)Cl)C)CC
Isomeric SMILES CCN(CCCC(Nc1c2cc(OC)ccc2nc2c1ccc(c2)Cl)C)CC
InChI InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
396 mepacrine
Synonyms Click here for help
Atabrine® | quinacrine
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9695421
Reactome Reaction Reactome logo R-HSA-9695415
Other databases
CAS Registry No. 83-89-6 (source: Scifinder)
ChEMBL Ligand CHEMBL7568
DrugBank Ligand DB01103
DrugCentral Ligand 2338
GtoPdb PubChem SID 381118882
PubChem CID 237
Search Google for chemical match using the InChIKey GPKJTRJOBQGKQK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GPKJTRJOBQGKQK
Search PubMed clinical trials mepacrine
Search PubMed titles mepacrine
Search PubMed titles/abstracts mepacrine
UniChem Compound Search for chemical match using the InChIKey GPKJTRJOBQGKQK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GPKJTRJOBQGKQK-UHFFFAOYSA-N
Wikipedia Mepacrine