Quinine
| Subclass of | Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-, quinidine, epiquinine |
|---|---|
| Get use | Medication |
| Stylized name | quiNINE |
| Stereoisomer of | epiquinidine |
| Chemical formula | C₂₀H₂₄N₂O₂ |
| 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 |
| Active ingredient in | Qualaquin |
| Medical condition treated | Babesiosis, muscle cramp, Plasmodium falciparum malaria |
| Physically dey interact plus | Potassium voltage-gated channel subfamily B member 2, Solute carrier family 29 member 4, taste receptor type 2 |
| Legal status (medicine) | boxed warning |
| Pregnancy category | Australian pregnancy category D, US pregnancy category C |
| LiverTox likelihood score | LiverTox toxicity likelihood category B |
| Natural product of taxon | Cinchona |
| Get characteristic | bitterness |
Quinine be a medication dem use to treat malaria den babesiosis.[1] Dis dey include de treatment of malaria secof Plasmodium falciparum wey be resistant to chloroquine wen artesunate no be available.[1][2] While dem sam times use am give nocturnal leg cramps, quinine no be recommended for dis purpose secof de risk of serious side effects.[1] Dem fi be take am by mouth anaa intravenously.[1] Malaria resistance to quinine dey occur insyd certain areas of de world.[3] Quinine sanso be used as an ingredient insyd tonic water den oda beverages to impart a bitter taste.[4]
Common side effects dey include headache, ringing insyd de ears, vision issues, den sweating.[1] More severe side effects dey include deafness, low blood platelets, den an irregular heartbeat.[1] Ein use fi make one more prone to sunburn.[1] While e be unclear if ein use during pregnancy dey carry potential for fetal harm, treating malaria during pregnancy .plus quinine wen appropriate still be recommended.[1] Quinine be an alkaloid, a naturally occurring chemical compound. E dey possess a C9H7N quinoline functional group (pyridine dem fuse to benzene).[1]
Quinine be first isolated insyd 1820 from de bark of a cinchona tree, wich be native to Peru,[1][5][6] den ein molecular formula be determined by Adolph Strecker insyd 1854.[7] De class of chemical compounds to wich e dey belong be thus called de cinchona alkaloids. Na bark extracts be used to treat malaria since at least 1632 wey e be introduced to Spain as early as 1636 by Jesuit missionaries wey dey return from de New World.[8] E dey on de World Health Organization's List of Essential Medicines.[9] Treatment of malaria plus quinine dey mark de first known use of a chemical compound to treat an infectious disease.[10]
References
[edit | edit source]- 1 2 3 4 5 6 7 8 9 10 "Quinine sulfate". Drugs.com. 20 February 2020. Retrieved 14 May 2020.
- ↑ Esu EB, Effa EE, Opie ON, Meremikwu MM (June 2019). "Artemether for severe malaria". The Cochrane Database of Systematic Reviews. 6 (6) CD010678. doi:10.1002/14651858.CD010678.pub3. PMC 6580442. PMID 31210357.
- ↑ Foley M, Tilley L (February 1997). "Quinoline antimalarials: mechanisms of action and resistance". International Journal for Parasitology. 27 (2): 231–240. doi:10.1016/s0020-7519(96)00152-x. PMID 9088993.
- ↑ Olmsted J, Williams GM (1997). Chemistry: The Molecular Science. Jones & Bartlett Learning. p. 137. ISBN 978-0-815-18450-8. Archived from the original on 15 September 2016.
- ↑ Willcox M (28 June 2004). Traditional Medicinal Plants and Malaria. CRC Press. p. 231. ISBN 978-0-203-50232-7.
- ↑ Cechinel-Filho V (2012). Plant bioactives and drug discovery: principles, practice, and perspectives. Hoboken, N.J.: John Wiley & Sons. p. 2. ISBN 978-0-470-58226-8. Archived from the original on 4 March 2016.
- ↑ Strecker A (1854). "Untersuchungen über die Constitution des Chinins". Liebigs Ann. Chem. 91 (2): 155–170. doi:10.1002/jlac.18540910204.
- ↑ Staines HM, Krishna S (2011). Treatment and Prevention of Malaria: Antimalarial Drug Chemistry, Action and Use. [S.l.]: Springer Verlag. p. 45. ISBN 978-3-0346-0479-6.
- ↑ The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. 2023. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
- ↑ "Quinine". Encyclopedia Britannica. Retrieved 12 November 2021.
External links
[edit | edit source]- Pages using Sister project links with hidden wikidata
- Quinine
- Antimalarial agents
- Bitter compounds
- CYP2D6 inhibitors
- Hepatotoxins
- Phenol ethers
- Quinoline alkaloids
- Quinuclidine alkaloids
- Secondary alcohols
- Vinyl compounds
- World Health Organization essential medicines
- Methoxy compounds
- Tree-derived bioactive compounds
- Translated from MDWiki