Chloroquine

Chloroquine
Clinical data
Pronunciation	/ˈklɔːrəkwiːn/
Trade names	Aralen, other
Other names	Chloroquine phosphate
AHFS/Drugs.com	Monograph
License data	US DailyMed: Chloroquine;
Routes of; administration	By mouth
ATC code	P01BA01 (WHO) P01BB52 (WHO);
Legal status
Legal status	UK: P (Pharmacy medicines); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver
Elimination half-life	1-2 months
Identifiers
	IUPAC name (RS)-N'-(7-chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine;
CAS Number	54-05-7 ;
PubChem CID	2719;
IUPHAR/BPS	5535;
DrugBank	DB00608 ;
ChemSpider	2618 ;
UNII	886U3H6UFF;
KEGG	D02366 ;
ChEBI	CHEBI:3638 ;
ChEMBL	ChEMBL76 ;
NIAID ChemDB	000733;
CompTox Dashboard (EPA)	DTXSID2040446 ;
ECHA InfoCard	100.000.175
Chemical and physical data
Formula	C18H26ClN3
Molar mass	319.88 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:WHTVZRBIWZFKQO-UHFFFAOYSA-N ;
	(verify)

Chloroquine is a medication primarily used to prevent and treat malaria in areas where malaria remains sensitive to its effects.^[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 was studied to treat COVID-19 early in the pandemic, but these studies were largely halted in the summer of 2020, and the NIH does not recommend its use for this purpose.^[3] It is taken by mouth.^[1]

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]

^ ^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.
^ "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.
^ "Chloroquine or Hydroxychloroquine". COVID-19 Treatment Guidelines. National Institutes of Health. Archived from the original on 28 August 2020. Retrieved 14 February 2021.
^ 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.
^ 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.
^ 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.
^ 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.

[AHFS2015-1] ^ ^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.

[:1-3] "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.

[WHO21st-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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