Structure via PubChem · Public domain (PubChem)
quinidine
Sign in to saveAlso known as Quinaglute®, Quinidex®, quinidine hydrochloride, 6-methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol, alpha-(6-methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol, beta-quinine, pitayine, conquinine
Quinidine is a class IA antiarrhythmic agent used to treat heart rhythm disturbances. It is a diastereomer of antimalarial agent quinine, originally derived from the bark of the cinchona tree. The drug causes increased action potential duration, as well as a prolonged QT interval. As of 2019, its IV formulation is no longer being manufactured for use in the United States.
Chemical data
- Formula
- C20H24N2O2
- Molecular weight
- 324.4 g/mol
- IUPAC name
- (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
- SMILES
- COC1=CC2=C(C=CN=C2C=C1)[C@@H]([C@H]3C[C@@H]4CCN3C[C@@H]4C=C)O
- InChIKey
- LOUPRKONTZGTKE-LHHVKLHASA-N
- XLogP
- 2.9
- Polar surface area
- 45.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1950
- Admin. routes
- oral, parenteral
- Indications
- cardiac arrhythmia, atrial fibrillation, myocardial infarction, sudden cardiac arrest
via ChEMBL · EBI
Research
9,490 papers- Quinidine.The New England journal of medicine · 1998
- Quinidine revisited.The American journal of medicine · 2009
- Quinidine.Annals of the New York Academy of Sciences · 1984
- Quinidine--a re-evaluation.The Medical clinics of North America · 1966
- Quinidine-induced rheumatic syndromes.Seminars in arthritis and rheumatism · 1995
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 324.184
- Has use
- medication
Show 12 more facts
- chemical formula
- C₂₀H₂₄N₂O₂
- significant drug interaction
- thioridazine
- medical condition treated
- atrial fibrillation
- subject has role
- bactericide
- canonical SMILES
- COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
- isomeric SMILES
- COC1=CC2=C(C=CN=C2C=C1)[C@@H]([C@H]3C[C@@H]4CCN3C[C@@H]4C=C)O
- defined daily dose
- 1.2
- melting point
- 170
- Commons category
- Quinidine
- different from
- quinine
- found in taxon
- Cinchona calisaya
- stylized name
- quiNIDine
Sources (7)
via Wikidata · CC0
~8 min read
Encyclopedic overview
13 sectionsContents
- Medical uses
- Other uses
- Side effects
- Pharmacology
- Pharmacodynamics
- Mechanism of action
- Pharmacokinetics
- Elimination
- History
- Chemistry
- Veterinary use
- References
- External links
Quinidine is a class IA antiarrhythmic agent used to treat heart rhythm disturbances. It is a diastereomer of antimalarial agent quinine, originally derived from the bark of the cinchona tree. The drug causes increased action potential duration, as well as a prolonged QT interval. As of 2019, its IV formulation is no longer being manufactured for use in the United States.
==Medical uses== Quinidine is occasionally used as a class I antiarrhythmic agent to prevent ventricular arrhythmias, particularly in Brugada Syndrome, although its safety in this indication is uncertain.
Excerpted from Wikipedia’s “quinidine” article, available under the CC BY-SA 4.0 licence.