Lurtotecan

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Lurtotecan
Lurtotecan.svg
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
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: RVFGKBWWUQOIOU-NDEPHWFRSA-N checkY
  • 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
  • O=C2OCC=1C(=O)N6/C(=C\C=1[C@@]2(O)CC)c5nc4cc3OCCOc3cc4c(c5C6)CN7CCN(C)CC7
Properties
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).
☒N verify (what is checkY☒N ?)

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

Lurtotecan synthesis[3]

References

  1. ^ Seiden, MV; Muggia, F; Astrow, A; Matulonis, U; Campos, S; Roche, M; Sivret, J; Rusk, J; Barrett, E (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". Adis Insight. Springer International Publishing AG. Retrieved 15 July 2016.
  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.; Lowery, M. W.; McDougald, D. L.; Meerholz, C. A.; Partridge, J. J.; Sharp, M. J.; Xie, S. (1997). "Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C". Tetrahedron. 53 (32): 10953. doi:10.1016/S0040-4020(97)00357-8.