quinidine   Click here for help

GtoPdb Ligand ID: 2342

Synonyms: Quinaglute® | Quinidex® | quinidine hydrochloride
Approved drug PDB Ligand Antimalarial Ligand
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
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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
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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
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Organic cation transporter 3
Multidrug and toxin extrusion 17
Selectivity at ion channels
Key to terms and symbols Click on species/strain names for details Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
KNa1.2 Rn Channel blocker Inhibition - - 1x10-3 2
Conc range: 1x10-3 M [2]
KNa1.1 Hs Channel blocker Antagonist - - 1x10-4 - 3x10-4 10
Conc range: 1x10-4 - 3x10-4 M [10]
K2P18.1 N/A Channel blocker - - - 1x10-4 - 2x10-4
Conc range: 1x10-4 - 2x10-4 M
KCa5.1 Hs Channel blocker - - - < 1x10-4 15
Conc range: < 1x10-4 M [15]
K2P16.1 Hs Channel blocker - - - 1x10-4 6
Conc range: 1x10-4 M [6]
KCa5.1 Mm Channel blocker - - - 2x10-5 16,20
Conc range: 2x10-5 M [16,20]
Kv1.5 Hs Channel blocker - 5.2 pKd - 14
pKd 5.2 [14]
Kv1.7 Hs Channel blocker - 4.8 pKd - 1
pKd 4.8 [1]
Kv10.1 Hs Channel blocker - 5.8 pIC50 - 12
pIC50 5.8 [12]
Kv4.2 Rn Channel blocker - 4.9 pIC50 - 3
pIC50 4.9 [3]
Nav1.5 Rn Channel blocker Pore blocker 4.4 – 5.0 pIC50 - 8,13
pIC50 4.4 – 5.0 [8,13]
Voltage: Physiological
KNa1.1 Rn Channel blocker - 4.0 pIC50 - 2,22
pIC50 4.0 [2,22]
Kv10.2 Hs Channel blocker Pore blocker 3.8 pIC50 - 5
pIC50 3.8 [5]
Kv1.4 Rn Channel blocker - 3.7 pIC50 - 21
pIC50 3.7 [21]
K2P6.1 Rn Channel blocker - - pIC50 < 1x10-4 11
pIC50 Conc range: < 1x10-4 M [11]
K2P5.1 Hs Channel blocker - - - - 9
[9]
K2P10.1 Rn Channel blocker - - - - 7
[7]
VRAC Hs Channel blocker - - - -
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Plasma membrane monoamine transporter Hs Inhibitor Inhibition 4.6 pKi - 4,18
pKi 4.6 (Ki 2.53x10-5 M) [4,18]