Lurtotecan

Lurtotecan
Names
	Preferred IUPAC name (8S)-8-Ethyl-8-hydroxy-15-[(4-methylpiperazin-1-yl)methyl]-2,3-dihydro-11H-[1,4]dioxino[2,3-g]pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-9,12(8H,14H)-dione
Identifiers
CAS Number	149882-10-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL305666 ;
ChemSpider	54919 ;
PubChem CID	60956;
UNII	4J1L80T08I ;
	InChI InChI=1S/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3/t28-/m0/s1 Key: RVFGKBWWUQOIOU-NDEPHWFRSA-N ; InChI=1/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3/t28-/m0/s1 Key: RVFGKBWWUQOIOU-NDEPHWFRBI;
	SMILES O=C2OCC=1C(=O)N6/C(=C\C=1[C@@]2(O)CC)c5nc4cc3OCCOc3cc4c(c5C6)CN7CCN(C)CC7;
Properties
Chemical formula	C28H30N4O6
Molar mass	518.561 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Lurtotecan is a semi-synthetic analog of camptothecin with antineoplastic activity. Liposomal lurtotecan was in clinical trials as a treatment for topotecan-resistant ovarian cancer,^[1] but was discontinued.^[2]

Synthesis

References

↑ Seiden, MV; Muggia, F; Astrow, A; Matulonis, U; Campos, S; Roche, M; Sivret, J; Rusk, J et al. (April 2004). "A Phase II Study of Liposomal Lurtotecan (OSI-211) in Patients with Topotecan Resistant Ovarian Cancer". Gynecologic Oncology 93 (1): 229–32. doi:10.1016/j.ygyno.2003.12.037. PMID 15047241.
↑ "Liposomal lurtotecan (OSI 211) on AdisInsight". Springer International Publishing AG. http://adisinsight.springer.com/drugs/800010410.
↑ Fang, F. G.; Bankston, D. D.; Huie, E. M.; Ross Johnson, M.; Kang, M. C.; Lehoullier, C. S.; Lewis, G. C.; Lovelace, T. C. et al. (1997). "Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C". Tetrahedron 53 (32): 10953. doi:10.1016/S0040-4020(97)00357-8.

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[1] Seiden, MV; Muggia, F; Astrow, A; Matulonis, U; Campos, S; Roche, M; Sivret, J; Rusk, J et al. (April 2004). "A Phase II Study of Liposomal Lurtotecan (OSI-211) in Patients with Topotecan Resistant Ovarian Cancer". Gynecologic Oncology 93 (1): 229–32. doi:10.1016/j.ygyno.2003.12.037. PMID 15047241.

[2] "Liposomal lurtotecan (OSI 211) on AdisInsight". Springer International Publishing AG. http://adisinsight.springer.com/drugs/800010410.

[3] Fang, F. G.; Bankston, D. D.; Huie, E. M.; Ross Johnson, M.; Kang, M. C.; Lehoullier, C. S.; Lewis, G. C.; Lovelace, T. C. et al. (1997). "Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C". Tetrahedron 53 (32): 10953. doi:10.1016/S0040-4020(97)00357-8.

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Lurtotecan

Topic: Chemistry

Synthesis

References