Chloroquine

Not to be confused with Hydroxychloroquine.

Chloroquine
Clinical data
Pronunciation/ˈklɔːrəkwiːn/
Trade namesAralen, other
Other namesChloroquine phosphate
AHFS/Drugs.comMonograph
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
Elimination half-life1-2 months
Identifiers
IUPAC name
  • (RS)-N'-(7-chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.175
Chemical and physical data
FormulaC18H26ClN3
Molar mass319.88 g·mol−1
3D model (JSmol)
SMILES
  • Clc1cc2nccc(c2cc1)NC(C)CCCN(CC)CC
InChI
  • InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21) Y
  • Key:WHTVZRBIWZFKQO-UHFFFAOYSA-N Y
  (verify)

Chloroquine is an antiparasitic medication that treats malaria. It works by increasing the levels of heme in the blood, a substance toxic to the malarial parasite. This kills the parasite and stops the infection from spreading.[1] Certain types of malaria, resistant strains, and complicated cases typically require different or additional medication.[1] Chloroquine is also occasionally used for amebiasis that is occurring outside the intestines, rheumatoid arthritis, and lupus erythematosus. [1] While it has not been formally studied in pregnancy, it appears safe.[1][2] It is taken by mouth.[1] It was studied to treat COVID-19 early in the pandemic, but these studies were largely halted in the northern summer of 2020, and the NIH does not recommend its use for this purpose.[3]

Common side effects include muscle problems, loss of appetite, diarrhea, and skin rash.[1] Serious side effects include problems with vision, muscle damage, seizures, and low blood cell levels.[1][4] Chloroquine is a member of the drug class 4-aminoquinoline.[1] As an antimalarial, it works against the asexual form of the malaria parasite in the stage of its life cycle within the red blood cell.[1] How it works in rheumatoid arthritis and lupus erythematosus is unclear.[1]

Chloroquine was discovered in 1934 by Hans Andersag.[5][6] It is on the World Health Organization's List of Essential Medicines.[7] It is available as a generic medication.[1]

  1. ^ a b c d e f g h i j k "Aralen Phosphate". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  2. ^ "Chloroquine Use During Pregnancy". Drugs.com. Archived from the original on 16 April 2019. Retrieved 16 April 2019. There are no controlled data in human pregnancies.
  3. ^ "Chloroquine or Hydroxychloroquine". COVID-19 Treatment Guidelines. National Institutes of Health. Archived from the original on 28 August 2020. Retrieved 14 February 2021.
  4. ^ Mittra RA, Mieler WG (2013). "Chapter 89 – Drug Toxicity of the Posterior Segment". Retina (Fifth ed.). W.B. Saunders. pp. 1532–1554. doi:10.1016/B978-1-4557-0737-9.00089-8. ISBN 978-1-4557-0737-9. Retrieved 25 March 2020.
  5. ^ Manson P, Cooke G, Zumla A, eds. (2009). Manson's tropical diseases (22nd ed.). [Edinburgh]: Saunders. p. 1240. ISBN 978-1-4160-4470-3. Archived from the original on 2 November 2018. Retrieved 9 September 2017.
  6. ^ Bhattacharjee M (2016). Chemistry of Antibiotics and Related Drugs. Springer. p. 184. ISBN 978-3-319-40746-3. Archived from the original on 1 November 2018. Retrieved 9 September 2017.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06.
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