Quinidine

Quinidine
Clinical data
Trade names	Quinaglute, Quinidex
Other names	(2-Ethenyl-4-azabicyclo[2.2.2]oct-5-yl)-(6-methoxyquinolin-4-yl)-methanol
AHFS/Drugs.com	Monograph
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
Bioavailability	70–85%
Metabolism	50–90% (by liver)
Elimination half-life	6–8 hours
Excretion	By 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 ;
PubChem CID	441074;
IUPHAR/BPS	2342;
DrugBank	DB00908 ;
ChemSpider	389880 ;
UNII	ITX08688JL;
KEGG	D08458 ;
ChEBI	CHEBI:28593 ;
ChEMBL	ChEMBL97 ;
CompTox Dashboard (EPA)	DTXSID4023549 ;
ECHA InfoCard	100.000.254
Chemical and physical data
Formula	C20H24N2O2
Molar mass	324.424 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 ; Key:LOUPRKONTZGTKE-LHHVKLHASA-N ;
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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]

^ Grace AA, Camm AJ (January 1998). "Quinidine". The New England Journal of Medicine. 338 (1): 35–45. doi:10.1056/NEJM199801013380107. PMID 9414330.
^ 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.
^ "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.