Quinine

Medication used to treat malaria and babesiosis / From Wikipedia, the free encyclopedia

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Quinine is a medication used to treat malaria and babesiosis.[4] This includes the treatment of malaria due to Plasmodium falciparum that is resistant to chloroquine when artesunate is not available.[4][5] While sometimes used for nocturnal leg cramps, quinine is not recommended for this purpose due to the risk of serious side effects.[4] It can be taken by mouth or intravenously.[4] Malaria resistance to quinine occurs in certain areas of the world.[4] Quinine is also used as an ingredient in tonic water to impart a bitter taste.[6]

Quick facts: Clinical data, Pronunciation, Trade names, AH... ▼
Quinine
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Quinine-3D-balls.png
Clinical data
PronunciationUS: /ˈkwaɪnaɪn/, /kwɪˈniːn/ or UK: /ˈkwɪniːn/ KWIN-een
Trade namesQualaquin, Quinbisul, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa682322
License data
Pregnancy
category
Routes of
administration		By mouth, intramuscular, intravenous, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding70–95%[3]
MetabolismLiver (mostly CYP3A4 and CYP2C19-mediated)
Elimination half-life8–14 hours (adults), 6–12 hours (children)[3]
ExcretionKidney (20%)
Identifiers
  • (R)-(6-Methoxyquinolin-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.550 Edit this at Wikidata
Chemical and physical data
FormulaC20H24N2O2
Molar mass324.424 g·mol−1
3D model (JSmol)
Melting point177 °C (351 °F)
  • [H][C@@]1([C@@H](C2=CC=NC3=CC=C(C=C23)OC)O)C[C@@H]4CC[N@]1C[C@@H]4C=C
  • 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-WZBLMQSHSA-N checkY
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Common side effects include headache, ringing in the ears, vision issues, and sweating.[4] More severe side effects include deafness, low blood platelets, and an irregular heartbeat.[4] Use can make one more prone to sunburn.[4] While it is unclear if use during pregnancy carries potential for fetal harm, treating malaria during pregnancy with quinine when appropriate is still recommended.[4] Quinine is an alkaloid, a naturally occurring chemical compound.[4] How it works as a medicine is not entirely clear.[4]

Quinine was first isolated in 1820 from the bark of a cinchona tree, which is native to Peru,[4][7][8] and its molecular formula was determined by Adolph Strecker in 1854.[9] The class of chemical compounds to which it belongs is thus called the cinchona alkaloids. Bark extracts had been used to treat malaria since at least 1632 and it was introduced to Spain as early as 1636 by Jesuit missionaries returning from the New World.[10] It is on the World Health Organization's List of Essential Medicines.[11][12] Treatment of malaria with quinine marks the first known use of a chemical compound to treat an infectious disease.[13]