Quinidine gluconateProduct ingredient for Quinidine
- Name
- Quinidine gluconate
- Drug Entry
- Quinidine
Quinidine is a D-isomer of quinine present in the bark of the Cinchona tree and similar plant species. This alkaloid was first described in 1848 and has a long history as an antiarrhythmic medication.1,2 Quinidine is considered the first antiarrhythmic drug (class Ia) and is moderately efficacious in the acute conversion of atrial fibrillation to normal sinus rhythm.1 It prolongs cellular action potential by blocking sodium and potassium currents. A phenomenon known as “quinidine syncope” was first described in the 1950s, characterized by syncopal attacks and ventricular fibrillation in patients treated with this drug.1 Due to its side effects and increased risk of mortality, the use of quinidine was reduced over the next few decades. However, it continues to be used in the treatment of Brugada syndrome, short QT syndrome and idiopathic ventricular fibrillation.2
- Accession Number
- DBSALT001251
- Structure
Structure for Quinidine gluconate (DBSALT001251)
- Synonyms
- Not Available
- UNII
- R6875N380F
- CAS Number
- 7054-25-3
- Weight
- Average: 520.579
Monoisotopic: 520.242080747 - Chemical Formula
- C26H36N2O9
- InChI Key
- XHKUDCCTVQUHJQ-LCYSNFERSA-N
- InChI
- InChI=1S/C20H24N2O2.C6H12O7/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;7-1-2(8)3(9)4(10)5(11)6(12)13/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2-5,7-11H,1H2,(H,12,13)/t13-,14-,19+,20-;2-,3-,4+,5-/m01/s1
- IUPAC Name
- (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid; (S)-[(1S,2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
- SMILES
- OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.COC1=CC=C2N=CC=C([C@H](O)[C@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)C2=C1
- External Links
- ChemSpider
- 10481901
- ChEBI
- 27502
- ChEMBL
- CHEMBL1200437
- Wikipedia
- Quinidine
- Predicted Properties
Property Value Source Water Solubility 0.334 mg/mL ALOGPS logP 2.82 ALOGPS logP 2.51 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 13.89 Chemaxon pKa (Strongest Basic) 9.05 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 45.59 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 94.69 m3·mol-1 Chemaxon Polarizability 35.97 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon