Hydroxychloroquine

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.

"HCQ" redirects here. For other uses, see HCQ (disambiguation).
Not to be confused with chloroquine.

Hydroxychloroquine
Skeletal formula of hydroxychloroquine
Ball-and-stick model of the hydroxychloroquine freebase molecule
Clinical data
Trade namesPlaquenil, others
Other namesHCQ
AHFS/Drugs.comMonograph
MedlinePlusa601240
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth (tablets)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityVariable (74% on average)
Protein binding45%
MetabolismLiver
Elimination half-life32–50 days
ExcretionMostly kidney (23–25% as unchanged drug), also biliary (<10%)
Identifiers
  • (RS)-2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.003.864
Chemical and physical data
FormulaC18H26ClN3O
Molar mass335.88 g·mol−1
3D model (JSmol)
SMILES
  • Clc1cc2nccc(c2cc1)NC(C)CCCN(CC)CCO
  • 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?)  (verify)

Common side effects may include vomiting, headache, blurred vision, and muscle weakness. Severe side effects may include allergic reactions, retinopathy, and irregular heart rate. Although all risk cannot be excluded, it remains a treatment for rheumatic disease during pregnancy. 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. In 2021, it was the 116th most commonly prescribed medication in the United States, with more than 5 million prescriptions.

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. Among studies that deemed hydroxychloroquine intake to cause harmful side effects, a publication by The Lancet was retracted due to data flaws. The speculative use of hydroxychloroquine for COVID-19 threatens its availability for people with established indications.

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