Dihydroartemisinin

Dihydroartemisinin
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability12%
MetabolismLiver
Elimination half-lifeAbout 4–11 hours
ExcretionMainly bile
Identifiers
  • (3R,5aS,6R,8aS,9R,12S,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.128.242 Edit this at Wikidata
Chemical and physical data
FormulaC15H24O5
Molar mass284.352 g·mol−1
3D model (JSmol)
  • O1[C@H](O)[C@@H](C4CC[C@@H](C)[C@H]3[C@@]42OOC(O[C@@H]12)(C)CC3)C
  • InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11?,12+,13-,14?,15-/m1/s1 checkY
  • Key:BJDCWCLMFKKGEE-KWWHLYHASA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dihydroartemisinin (also known as dihydroqinghaosu, artenimol or DHA) is a drug used to treat malaria. Dihydroartemisinin is the active metabolite of all artemisinin compounds (artemisinin, artesunate, artemether, etc.) and is also available as a drug in itself. It is a semi-synthetic derivative of artemisinin and is widely used as an intermediate in the preparation of other artemisinin-derived antimalarial drugs.[1] It is sold commercially in combination with piperaquine and has been shown to be equivalent to artemether/lumefantrine.[2]

  1. ^ Woo SH, Parker MH, Ploypradith P, Northrop J, Posner GH (1998). "Direct conversion of pyranose anomeric OH→F→R in the artemisinin family of antimalarial trioxanes". Tetrahedron Letters. 39 (12): 1533–6. doi:10.1016/S0040-4039(98)00132-4.
  2. ^ Arinaitwe E, Sandison TG, Wanzira H, Kakuru A, Homsy J, Kalamya J, et al. (December 2009). "Artemether-lumefantrine versus dihydroartemisinin-piperaquine for falciparum malaria: a longitudinal, randomized trial in young Ugandan children". Clinical Infectious Diseases. 49 (11): 1629–1637. doi:10.1086/647946. PMID 19877969.