Artelinic acid

Artelinic acid

Systematic (IUPAC) name
4-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro- 3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2- benzodioxepin-10-yl]oxy]methylbenzoic acid
Identifiers
CAS Number	120020-26-0
ATC code	None
PubChem	CID 180423 beta-Artelinic acid: CID 10341948
ChemSpider	8517407
ChEMBL	CHEMBL477080
Chemical data
Formula	C23H30O7
Molar mass	418.48 g/mol
SMILES O=C(O)c1ccc(cc1)CO[C@H]4O[C@@H]5O[C@@]3(OO[C@]52[C@@H](CC[C@@H](C)[C@@H]2CC3)[C@H]4C)C
InChI InChI=1S/C23H30O7/c1-13-4-9-18-14(2)20(26-12-15-5-7-16(8-6-15)19(24)25)27-21-23(18)17(13)10-11-22(3,28-21)29-30-23/h5-8,13-14,17-18,20-21H,4,9-12H2,1-3H3,(H,24,25)/t13-,14-,17+,18+,20+,21-,22-,23-/m1/s1 Key:UVNHKOOJXSALHN-ILQPJIFQSA-N
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Artelinic acid (or its salt, artelinate) is an experimental drug that is being investigated as a treatment for malaria.^[1] It is a semi-synthetic derivative of the natural compound artemisinin. Artelinic acid has a lower rate of neurotoxicity than the related artemisin derivatives arteether and artemether,^[2] but is three times more toxic than artesunate.^[3] At present, artelinic acid seems unlikely to enter routine clinical use, because it offers no clear benefits over the artemesinins already available (artesunate and artemether). Artelinic acid has not yet been evaluated for use in humans.

References

1. Bustos MD, Gay F, Diquet B. (1994). "In-vitro tests on Philippine isolates of Plasmodium falciparum against four standard antimalarials and four qinghaosu derivatives.". Bull World Health Org 72: 729–35.
2. Genovese RF, Newman DB, Brewer TG (2000). "Behavioural and neural toxicity of the artemisinin antimalarial, arteether, but not artesunate and artelinate, in rats". Pharmacol Biochem Behav 67 (1): 37–44. doi:10.1016/S0091-3057(00)00309-9. PMID 11113482.
3. Li Q, Xie LH, Johnson TO; et al. (2007). "Toxicity exaluation of artesunate and artelinate in Plasmodium berghei-infected and uninfected rats". Trans R Soc Trop Med Hyg Z 101 (2): 104–12. doi:10.1016/j.trstmh.2006.04.010. PMID 16860356.