Quinine
Medicinal Chemistry
Molecular Weight
324.42
Molecular Formula
C20H24N2O2
IUPAC Name
(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]oct-2-yl](6-methoxyquinolin-4-yl)methanol
Pharmacognosy
Biological Source
Cinchona calisaya, Cinchona succirubra
Active Constituents
Quinine, Cinchonine
Pharmacology & Synthesis
Mechanism of Action
Interferes with heme polymerization in malaria parasites, intercalates into DNA.
Pharmacokinetics (ADME)
A: Well absorbed.
D: Widely distributed.
M: Hepatic via CYP3A4.
E: Renal.
Pharmacodynamics
Schizonticidal against all malaria species; skeletal muscle relaxant.
Synthesis Pathway
Synthesized from tryptophan and secologanin via strictosidine.
Safety, Warnings & Interactions
Adverse Effects
Cinchonism (tinnitus, headache, deafness), hypoglycemia.
Contraindications
G6PD deficiency, optic neuritis.
Drug Interactions
Antacids delay absorption; prolongs QT with mefloquine.
Pharmaceutics & Compendia
Dosage Forms
Capsules, Tablets, Injection
Official Compendia
IP, BP, USP