Hydroxychloroquine

Hydroxychloroquine
	Skeletal formula of hydroxychloroquine
	Ball-and-stick model of the hydroxychloroquine freebase molecule
Clinical data
Trade names	Plaquenil, others
Other names	HCQ
AHFS/Drugs.com	Monograph
MedlinePlus	a601240
License data	US DailyMed: Hydroxychloroquine;
Pregnancy; category	AU: D; ;
Routes of; administration	By mouth (tablets)
ATC code	P01BA02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Variable (74% on average)
Protein binding	45%
Metabolism	Liver
Elimination half-life	32–50 days
Excretion	Mostly kidney (23–25% as unchanged drug), also biliary (<10%)
Identifiers
	IUPAC name (RS)-2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol;
CAS Number	118-42-3 ;
PubChem CID	3652;
IUPHAR/BPS	7198;
DrugBank	DB01611 ;
ChemSpider	3526 ;
UNII	4QWG6N8QKH;
KEGG	D08050 ; C07043 ;
ChEBI	CHEBI:5801 ;
ChEMBL	ChEMBL1535 ;
CompTox Dashboard (EPA)	DTXSID8023135 ;
ECHA InfoCard	100.003.864
Chemical and physical data
Formula	C18H26ClN3O
Molar mass	335.88 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1cc2nccc(c2cc1)NC(C)CCCN(CC)CCO;
	InChI InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21) ; Key:XXSMGPRMXLTPCZ-UHFFFAOYSA-N ;
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Hydroxychloroquine, sold under the brand name Plaquenil among others, is a medication used to prevent and treat malaria in areas where malaria remains sensitive to chloroquine. Other uses include treatment of rheumatoid arthritis, lupus, and porphyria cutanea tarda. It is taken by mouth, often in the form of hydroxychloroquine sulfate.^[3]

Common side effects may include vomiting, headache, blurred vision, and muscle weakness.^[3] Severe side effects may include allergic reactions, retinopathy, and irregular heart rate.^[3]^[4] Although all risk cannot be excluded, it remains a treatment for rheumatic disease during pregnancy.^[5] Hydroxychloroquine is in the antimalarial and 4-aminoquinoline families of medication.^[3]

Hydroxychloroquine was approved for medical use in the United States in 1955.^[3] It is on the World Health Organization's List of Essential Medicines.^[6] In 2021, it was the 116th most commonly prescribed medication in the United States, with more than 5 million prescriptions.^[7]^[8]

Hydroxychloroquine has been studied for an ability to prevent and treat coronavirus disease 2019 (COVID-19), but clinical trials found it ineffective for this purpose and a possible risk of dangerous side effects.^[9] Among studies that deemed hydroxychloroquine intake to cause harmful side effects, a publication by The Lancet was retracted due to data flaws.^[10] The speculative use of hydroxychloroquine for COVID-19 threatens its availability for people with established indications.^[11]

^ "Hydroxychloroquine Use During Pregnancy". Drugs.com. 28 February 2020. Retrieved 21 March 2020.
^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ ^a ^b ^c ^d ^e "Hydroxychloroquine Sulfate Monograph for Professionals". The American Society of Health-System Pharmacists. 20 March 2020. Archived from the original on 20 March 2020. Retrieved 20 March 2020.
^ Cite error: The named reference mayoclinic1 was invoked but never defined (see the help page).
^ Flint J, Panchal S, Hurrell A, van de Venne M, Gayed M, Schreiber K, et al. (BSR and BHPR Standards, Guidelines and Audit Working Group) (September 2016). "BSR and BHPR guideline on prescribing drugs in pregnancy and breastfeeding-Part I: standard and biologic disease modifying anti-rheumatic drugs and corticosteroids". Rheumatology. 55 (9): 1693–7. doi:10.1093/rheumatology/kev404. PMID 26750124.
^ World Health Organization (2023). 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. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Hydroxychloroquine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
^ "Chloroquine or Hydroxychloroquine". COVID-19 Treatment Guidelines. National Institutes of Health. Archived from the original on 28 August 2020. Retrieved 14 February 2021.
^ Edwards E (4 June 2020). "The Lancet retracts large study on hydroxychloroquine". NBC News. Retrieved 4 January 2021.
^ Cite error: The named reference Juurlink2020 was invoked but never defined (see the help page).

[Drugs.com_pregnancy-1] "Hydroxychloroquine Use During Pregnancy". Drugs.com. 28 February 2020. Retrieved 21 March 2020.

[2] "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.

[AHFS2020-3] "Hydroxychloroquine Sulfate Monograph for Professionals". The American Society of Health-System Pharmacists. 20 March 2020. Archived from the original on 20 March 2020. Retrieved 20 March 2020.

[mayoclinic1-4] Cite error: The named reference mayoclinic1 was invoked but never defined (see the help page).

[5] Flint J, Panchal S, Hurrell A, van de Venne M, Gayed M, Schreiber K, et al. (BSR and BHPR Standards, Guidelines and Audit Working Group) (September 2016). "BSR and BHPR guideline on prescribing drugs in pregnancy and breastfeeding-Part I: standard and biologic disease modifying anti-rheumatic drugs and corticosteroids". Rheumatology. 55 (9): 1693–7. doi:10.1093/rheumatology/kev404. PMID 26750124.

[WHO23rd-6] World Health Organization (2023). 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. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[7] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[8] "Hydroxychloroquine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[nih-9] "Chloroquine or Hydroxychloroquine". COVID-19 Treatment Guidelines. National Institutes of Health. Archived from the original on 28 August 2020. Retrieved 14 February 2021.

[10] Edwards E (4 June 2020). "The Lancet retracts large study on hydroxychloroquine". NBC News. Retrieved 4 January 2021.

[Juurlink2020-11] Cite error: The named reference Juurlink2020 was invoked but never defined (see the help page).

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