Hydroxychloroquine

Hydroxychloroquine

Clinical data
Trade names	Plaquenil, others
AHFS/Drugs.com	Monograph
MedlinePlus	a601240
Pregnancy category	AU: D US: C (Risk not ruled out)
Routes of administration	By mouth (tablets)
ATC code	P01BA02 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Variable (74% on average); Tmax = 2–4.5 hours
Protein binding	45%
Metabolism	Liver
Biological 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 Y
PubChem (CID)	3652
IUPHAR/BPS	7198
DrugBank	DB01611 Y
ChemSpider	3526 Y
UNII	4QWG6N8QKH Y
KEGG	D08050 Y
ChEBI	CHEBI:5801 N
ChEMBL	CHEMBL1535 Y
ECHA InfoCard	100.003.864
Chemical and physical data
Formula	C18H26ClN3O
Molar mass	335.872 g/mol
3D model (Jmol)	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) Y Key:XXSMGPRMXLTPCZ-UHFFFAOYSA-N Y
NY (what is this?)

Hydroxychloroquine (HCQ), sold under the brand names Plaquenil among others, is a medication used for the prevention and treatment of certain types of malaria. Specifically it is used for chloroquine sensitive malaria. Other uses include rheumatoid arthritis, lupus, and porphyria cutanea tarda. It is taken by mouth.

Common side effects include vomiting, headache, changes in vision, and muscle weakness. Severe side effects may include allergic reactions. It appears to be safe in pregnancy but this use has not been well studied. Hydroxychloroquine is in the antimalarial and 4-aminoquinoline families of medication.

Hydroxychloroquine was approved for medical use in the United States in 1955. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 5.40 to 7.44 USD per month. In the United Kingdom this dose costs the NHS about 5.15 pounds. In the United States a month of treatment costs less than 25 USD.

Hydroxychloroquine has been used for many years to treat malaria. It is also used to treat systemic lupus erythematosus, rheumatic disorders like rheumatoid arthritis and Sjögren's syndrome, and porphyria cutanea tarda. Its efficacy to treat Sjögren's syndrome has recently been called into question in a double-blind study involving 120 patients over a 48-week period. Hydroxychloroquine increases lysosomal pH in antigen-presenting cells. In inflammatory conditions, it blocks toll-like receptors on plasmacytoid dendritic cells (PDCs).Toll-like receptor 9 (TLR 9), which recognizes DNA-containing immune complexes, leads to the production of interferon and causes the dendritic cells to mature and present antigen to T cells. Hydroxychloroquine, by decreasing TLR signaling, reduces the activation of dendritic cells and the inflammatory process.