quinidine   

GtoPdb Ligand ID: 2342

Synonyms: Quinaglute® | Quinidex® | quinidine hydrochloride
quinidine is an approved drug (FDA (1950))
Comment: Quinidine is a stereoisomer of quinine. It acts as a class I antiarrhythmic agent, blocking the fast inward sodium current (INa).

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
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 45.59
Molecular weight 324.18
XLogP 2.6
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES C=CC1CN2CCC1CC2C(c1ccnc2c1cc(OC)cc2)O
Isomeric SMILES C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cc(OC)cc2)O
InChI InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-/m0/s1
InChI Key LOUPRKONTZGTKE-LHHVKLHASA-N
Classification
Compound class Natural product or derivative
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1950))
IUPAC Name
(S)-[(4S,5R,7R)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol
Synonyms
Quinaglute® | Quinidex® | quinidine hydrochloride
Database Links
BindingDB Ligand 50121975
CAS Registry No. 56-54-2 (source: Scifinder)
ChEBI CHEBI:127150
ChEMBL Ligand CHEMBL1294
DrugBank Ligand DB00908
DrugCentral Ligand 2346
GtoPdb PubChem SID 135650872
PubChem CID 441074
RCSB PDB Ligand QDN
Search Google for chemical match using the InChIKey LOUPRKONTZGTKE-LHHVKLHASA-N
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Search UniChem for chemical match using the InChIKey LOUPRKONTZGTKE-LHHVKLHASA-N
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Wikipedia Quinidine