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Quinidine information


Quinidine
Clinical data
Trade namesQuinaglute, Quinidex
Other names(2-Ethenyl-4-azabicyclo[2.2.2]oct-5-yl)-(6-methoxyquinolin-4-yl)-methanol
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: C
Routes of
administration
By mouth, intramuscular injection, intravenous
ATC code
  • C01BA01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability70–85%
Metabolism50–90% (by liver)
Elimination half-life6–8 hours
ExcretionBy the liver (20% as unchanged quinidine via urine)
Identifiers
IUPAC name
  • (S)-(6-Methoxyquinolin-4-yl)[(1S,2R,4S,5R)-5-vinylquinuclidin-2-yl]methanol
CAS Number
  • 56-54-2 checkY
PubChem CID
  • 441074
IUPHAR/BPS
  • 2342
DrugBank
  • DB00908 checkY
ChemSpider
  • 389880 checkY
UNII
  • ITX08688JL
KEGG
  • D08458 ☒N
ChEBI
  • CHEBI:28593 checkY
ChEMBL
  • ChEMBL97 ☒N
CompTox Dashboard (EPA)
  • DTXSID4023549 Edit this at Wikidata
ECHA InfoCard100.000.254 Edit this at Wikidata
Chemical and physical data
FormulaC20H24N2O2
Molar mass324.424 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O(c4cc1c(nccc1[C@H](O)[C@@H]2N3CC[C@@H](C2)[C@@H](/C=C)C3)cc4)C
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 checkY
  • Key:LOUPRKONTZGTKE-LHHVKLHASA-N checkY
 ☒NcheckY (what is this?)  (verify)

Quinidine is a class IA antiarrhythmic agent used to treat heart rhythm disturbances.[1] It is a diastereomer of antimalarial agent quinine,[2] 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.[3]

  1. ^ Grace AA, Camm AJ (January 1998). "Quinidine". The New England Journal of Medicine. 338 (1): 35–45. doi:10.1056/NEJM199801013380107. PMID 9414330.
  2. ^ Shiomi S, Misaka R, Kaneko M, Ishikawa H (November 2019). "Enantioselective total synthesis of the unnatural enantiomer of quinine". Chemical Science. 10 (41): 9433–9437. doi:10.1039/c9sc03879e. PMC 7020653. PMID 32110303.
  3. ^ "Artesunate Now First-Line Treatment for Severe Malaria in the United States". CDC Online Newsroom. U.S. Centers for Disease Control and Prevention. 28 March 2019. Retrieved 6 April 2019.

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Quinidine

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Quinidine is a class IA antiarrhythmic agent used to treat heart rhythm disturbances. It is a diastereomer of antimalarial agent quinine, originally derived...

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agents. In 2010, the FDA approved the combination drug dextromethorphan/quinidine under the brand name Nuedexta for the treatment of pseudobulbar affect...

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Pseudobulbar affect

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dextromethorphan hydrobromide 30 mg/quinidine sulfate 10 mg (N=110) Nuedexta – dextromethorphan hydrobromide 20 mg/quinidine sulfate 10 mg (N=107) 283 patients...

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heart rate, there are rare instances of dysrhythmia and AV node block. Quinidine should not be used concurrently with calcium channel blockers because...

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Quinoline Yellow WS

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names C.I. Acid Yellow 3 Food Yellow 13 D&C Yellow No. 10 Acid yellow 3 Quinidine Yellow KT Japan Yellow 203 Lemon Yellow ZN 3 C.I. 47005 Identifiers CAS...

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Sodium channel blocker

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intravenous formulations are still available. While procainamide and quinidine may be used in the conversion of atrial fibrillation to normal sinus rhythm...

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Disopyramide

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intravenous forms. In 1972, when it was one of the only alternatives to quinidine, it was praised for being more potent and somewhat less toxic. However...

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Ammonium thiocyanate

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drinks by colorimetry. Ammonium thiocyanate may also be used to separate quinidine, from liquors, after the isolation of quinine from the neutral, aqueous...

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Sinus bradycardia

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pressure Medications, most commonly: digitalis glycosides, beta-blockers, quinidine, adenosine, calcium channel blockers, class I antiarrhythmic agents, ivabradine...

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Brugada syndrome

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those who have frequent life-threatening abnormal heart rhythms, while quinidine may be used longer term. Testing people's family members may be recommended...

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Amaurosis

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Amaurosis (Greek meaning darkening, dark, or obscure) is vision loss or weakness that occurs without an apparent lesion affecting the eye. It may result...

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Acetazolamide

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primidone. Hence reducing anticonvulsant effect. Quinidine, reduces urinary excretion of quinidine, hence increasing the potential for toxicity. Salicylates...

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Loperamide

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a P-glycoprotein inhibitor. Common P-glycoprotein inhibitors include quinidine, ritonavir, and ketoconazole. Loperamide is capable of decreasing the...

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Quinine

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half dose. No injectable preparation of quinine is licensed in the US; quinidine is used instead. Quinine is a flavor component of tonic water and bitter...

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Procainamide

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Indonesia in World War II, the source for cinchona alkaloids, a precursor of quinidine, was reduced. This led to research for a new antiarrhythmic drug. As a...

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Itraconazole

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amiodarone (Cordarone); cisapride dofetilide nisoldipine alcohol pimozide quinidine lurasidone lovastatin or simvastatin midazolam or triazolam ergot medicines...

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Rilmenidine

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nefazodone, trazodone, triazoledione) Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine Spiperone Talipexole Tamsulosin Terazosin Tiodazosin...

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Cocaine

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Linopirdine Lolitrem B Maurotoxin Nifekalant Notoxin Paxilline Pinokalant Quinidine ShK-186 Sotalol Tedisamil Terikalant Tetraethylammonium Vernakalant hERG...

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Methamphetamine

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(pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine See...

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Coombs test

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Methyldopa (IgG mediated type II hypersensitivity) Penicillin (high dose) Quinidine (IgM mediated activation of classical complement pathway and Membrane...

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Cinchona

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Pelletier and Joseph Bienaimé Caventou in 1820. Two more key alkaloids, quinidine and cinchonidine, were later identified and it became a routine in quinology...

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Chlorpromazine

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hypotension experienced by those receiving chlorpromazine treatment. Quinidine may interact with chlorpromazine to increase myocardial depression. Likewise...

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Ipratropium bromide

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anticholinergics like tricyclic antidepressants, anti-Parkinson drugs and quinidine, which theoretically increase side effects, are clinically irrelevant...

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Phytochemistry

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(opium poppy), nicotine (tobacco), reserpine (Rauvolfia serpentina), quinidine and quinine (Cinchona), vincamine (Vinca minor), and vincristine (Catharanthus...

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Cinchona officinalis

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that are extracted from this tree include cinchonine, cinchonidine and quinidine. Standley, Paul C. (1936). "Rubiaceae". In Macbride, J.F. (ed.). Flora...

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Cinchonism

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therapeutic doses of quinine, either from one or several large doses. Quinidine (a Class 1A anti-arrhythmic) can also cause cinchonism symptoms to develop...

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