Artelinic acid

Artelinic acid
Clinical data
ATC code	none;
Identifiers
	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;
CAS Number	120020-26-0 ;
PubChem CID	180423; beta-Artelinic acid: 10341948;
ChemSpider	8517407 ;
UNII	08X93406PG;
ChEMBL	ChEMBL477080 ;
Chemical and physical data
Formula	C23H30O7
Molar mass	418.486 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(what is this?) (verify)

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 artemisinin derivatives arteether and artemether,^[2] but is three times more toxic than artesunate.^[3] At present,^[when?] 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.^[when?]

References

^ 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 Organ. 72 (5): 729–35. PMC 2486549. PMID 7955021.
^ 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. S2CID 21246490.
^ 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.

[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 Organ. 72 (5): 729–35. PMC 2486549. PMID 7955021.

[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. S2CID 21246490.

[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.

[1]

[2]

[3]

Clinical data

ATC code	none
Identifiers
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
CAS Number	120020-26-0^Y
PubChem CID	180423 beta-Artelinic acid: 10341948
ChemSpider	8517407^N
UNII	08X93406PG
ChEMBL	ChEMBL477080^N
Chemical and physical data
Formula	C₂₃H₃₀O₇
Molar mass	418.486 g·mol⁻¹
3D model (JSmol)	Interactive image
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^N Key:UVNHKOOJXSALHN-ILQPJIFQSA-N^N
^NY (what is this?) (verify)

Artelinic acid

References

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