Artesunate

drugbox
IUPAC_name =

---

CAS_number = 83507-69-1
CAS_supplemental = CAS|80155-81-3 (sodium salt)
ATC_prefix = P01
ATC_suffix = BE03
PubChem = 5464098
DrugBank =
C = 19 | H = 28 | O = 8
molecular_weight = 384.421 g/mol
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
excretion =
pregnancy_AU =
pregnancy_US =
pregnancy_category =
legal_AU =
legal_CA =
legal_UK =
legal_US =
legal_status = Not licensed in UK or US
routes_of_administration = oral, IV, IM

Artesunate (INN) is part of the artemisinin group of drugs that treat malaria. It is a semi-synthetic derivative of artemisinin that is water-soluble and may therefore be given by injection. It is sometimes abbreviated AS.Artesunate is prepared from Dihydroartemisinin (DHA) by reacting it with succinic acid anhydride in basic medium. Pyridine as base/solvent, sodium bicarbonate in chloroform and catalyst DMAP (N, N-Dimethylaminopyridine) and triethylamine in 1,2-dichloroethane have been used, with yields of up to 100%. A large scale process involves treatment of DHA in dichloromethane with a mixture of pyridine, a catalytic amount of DMAP and succinic anhydride. The dichloromethane mixture is stirred for 6-9 h to get artesunate in quantitative yield. The product is further re-crystallized from dichloromethane. alpha-Artesunate is exclusively formed (m.p 135-137˚C).

Uses

Artesunate is used primarily as treatment for malaria; but it has also been shown to be >90% efficacious at reducing egg production in "Schistosoma haematobium" infection. [cite journal | author=Boulangier D, Dieng Y, Cisse B, "et al." | title=Antischistosomal efficacy of artesunate combination therapies administered as curative treatments for malaria attacks | year=2007 | journal=Trans R Soc Trop Med Hyg | volume=101 | issue=2 | pages=113–16 | doi=10.1016/j.trstmh.2006.03.003 ]

Dosing

There are no licensed forms of artesunate available in the U.S. or UK. In the UK, artesunate is available on a named patient basis only.

Intravenous dose of IV artesunate:
*2.4 mg/kg loading dose over 5 minutes
*1.2 mg/kg dose 12 hours later
*1.2 mg/kg once daily after that

Artesunate must always be given with another antimalarial such as mefloquine [cite journal | journal=Lancet | year=1992 | volume=339 | issue=8797 | pages=821–4 | title=Randomised trial of artesunate and mefloquine alone and in sequence for acute uncomplicated falciparum malaria | author=Looareesuwan S, Viravan C, Vanijanonta S, "et al." | pmid=1347854 | doi=10.1016/0140-6736(92)90276-9 ] [cite journal | author=Nosten F, van Vugt M, Price R, "et al." | title=Effects of artesunate-mefloquine combination on incidence of Plasmodium falciparum malaria and mefloquine resistance in western Thailand: a prospective study | journal=Lancet | year=2000 | volume=356 | issue=9226 | pages=297–302 | pmid=11071185 | doi=10.1016/S0140-6736(00)02505-8 ] or amodiaquine [cite journal | journal=Lancet | year=2002 | volume=359 | issue=9315 | pages=1365–72 | title=Amodiaquine-artesunate versus amodiaquine for uncomplicated Plasmodium falciparum malaria in African children: a randomised, multicentre trial | author=Adjuik M, Agnamey P, Babiker A, "et al." | pmid=11978332 | doi=10.1016/S0140-6736(02)08348-4 ] so as to avoid the development of resistance. The combination of artesunate/amodiaquine has been found to be of equivalence to co-artemether. [cite journal | journal=Malar J | year=2006 | volume=5 | pages=43 | title=Artemether-lumefantrine versus artesunate plus amodiaquine for treating uncomplicated childhood malaria in Nigeria: randomized controlled trial | author=Meremikwu M, Alaribe A, Ejemot R, "et al." | pmid=16704735 | doi=10.1186/1475-2875-5-43 ]

References