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.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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)
InChI Key GPKJTRJOBQGKQK-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
N'-(6-chloro-2-methoxyacridin-9-yl)-N,N-diethylpentane-1,4-diamine
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
CAS Registry No. 83-89-6 (source: Scifinder)
ChEBI CHEBI:8711
ChEMBL Ligand CHEMBL7568
DrugBank Ligand DB01103
DrugCentral Ligand 2338
GtoPdb PubChem SID 381118882
PubChem CID 237
RCSB PDB Ligand QUN
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Wikipedia Mepacrine