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Artesunate
Systematic (IUPAC) name
	?
Identifiers
CAS number	83507-69-1 80155-81-3 (sodium salt)
ATC code	P01BE03
PubChem	5464098
Chemical data
Formula	C19H28O8
Mol. mass	384.421 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Not licensed in UK or US
Routes	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.

[edit] 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.^[1]

[edit] 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^[2]^[3] or amodiaquine^[4] so as to avoid the development of resistance. The combination of artesunate/amodiaquine has been found to be of equivalence to co-artemether.^[5]

[edit] Synthesis

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).

[edit] Drug resistance

Clinical evidence of drug resistance has appeared in Western Cambodia, where artemesinin monotherapy is common.^[6] There are as yet no reports of resistance emerging elsewhere.

[edit] References

^ Boulangier D, Dieng Y, Cisse B, et al. (2007). "Antischistosomal efficacy of artesunate combination therapies administered as curative treatments for malaria attacks". Trans R Soc Trop Med Hyg 101 (2): 113–16. doi:10.1016/j.trstmh.2006.03.003.
^ Looareesuwan S, Viravan C, Vanijanonta S, et al. (1992). "Randomised trial of artesunate and mefloquine alone and in sequence for acute uncomplicated falciparum malaria". Lancet 339 (8797): 821–4. doi:10.1016/0140-6736(92)90276-9. PMID 1347854.
^ Nosten F, van Vugt M, Price R, et al. (2000). "Effects of artesunate-mefloquine combination on incidence of Plasmodium falciparum malaria and mefloquine resistance in western Thailand: a prospective study". Lancet 356 (9226): 297–302. doi:10.1016/S0140-6736(00)02505-8. PMID 11071185.
^ Adjuik M, Agnamey P, Babiker A, et al. (2002). "Amodiaquine-artesunate versus amodiaquine for uncomplicated Plasmodium falciparum malaria in African children: a randomised, multicentre trial". Lancet 359 (9315): 1365–72. doi:10.1016/S0140-6736(02)08348-4. PMID 11978332.
^ Meremikwu M, Alaribe A, Ejemot R, et al. (2006). "Artemether-lumefantrine versus artesunate plus amodiaquine for treating uncomplicated childhood malaria in Nigeria: randomized controlled trial". Malar J 5: 43. doi:10.1186/1475-2875-5-43. PMID 16704735.
^ White NJ (2008). "Qinghaosu (Artemisinin): The price of success". Science 320 (5874): 330–334. doi:10.1126/science.1155165. PMID 18420924.

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[0] Boulangier D, Dieng Y, Cisse B, et al. (2007). "Antischistosomal efficacy of artesunate combination therapies administered as curative treatments for malaria attacks". Trans R Soc Trop Med Hyg 101 (2): 113–16. doi:10.1016/j.trstmh.2006.03.003.

[1] Looareesuwan S, Viravan C, Vanijanonta S, et al. (1992). "Randomised trial of artesunate and mefloquine alone and in sequence for acute uncomplicated falciparum malaria". Lancet 339 (8797): 821–4. doi:10.1016/0140-6736(92)90276-9. PMID 1347854.

[2] Nosten F, van Vugt M, Price R, et al. (2000). "Effects of artesunate-mefloquine combination on incidence of Plasmodium falciparum malaria and mefloquine resistance in western Thailand: a prospective study". Lancet 356 (9226): 297–302. doi:10.1016/S0140-6736(00)02505-8. PMID 11071185.

[3] Adjuik M, Agnamey P, Babiker A, et al. (2002). "Amodiaquine-artesunate versus amodiaquine for uncomplicated Plasmodium falciparum malaria in African children: a randomised, multicentre trial". Lancet 359 (9315): 1365–72. doi:10.1016/S0140-6736(02)08348-4. PMID 11978332.

[4] Meremikwu M, Alaribe A, Ejemot R, et al. (2006). "Artemether-lumefantrine versus artesunate plus amodiaquine for treating uncomplicated childhood malaria in Nigeria: randomized controlled trial". Malar J 5: 43. doi:10.1186/1475-2875-5-43. PMID 16704735.

[5] White NJ (2008). "Qinghaosu (Artemisinin): The price of success". Science 320 (5874): 330–334. doi:10.1126/science.1155165. PMID 18420924.

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Contents

[edit] Uses

[edit] Dosing

[edit] Synthesis

[edit] Drug resistance

[edit] References