TNP-470

Last updated
TNP-470
TNP-470 structure.png
Names
Preferred IUPAC name
[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] N-(2-chloroacetyl)carbamate
Other names
TNP-470, O-(chloroacetylcarbamoyl)fumagillol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.189.666 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 663-348-8
PubChem CID
UNII
  • InChI=1S/C19H28ClNO6/c1-11(2)5-6-13-18(3,27-13)16-15(24-4)12(7-8-19(16)10-25-19)26-17(23)21-14(22)9-20/h5,12-13,15-16H,6-10H2,1-4H3,(H,21,22,23)/t12-,13-,15-,16-,18+,19+/m1/s1
    Key: MSHZHSPISPJWHW-PVDLLORBSA-N
  • CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)NC(=O)CCl)OC)C
Properties
C19H28ClNO6
Molar mass 401.88 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

TNP-470 is an methionine aminopeptidase 2 inhibitor. Although it was one of the first angiogenesis inhibitor tested in clinical trials, its potential was hampered by neurotoxic effects and lack of effectiveness. [1] [2] [3]

References

  1. ↑ Goya Grocin, Andrea; Kallemeijn, Wouter W.; Tate, Edward W. (October 2021). "Targeting methionine aminopeptidase 2 in cancer, obesity, and autoimmunity". Trends in Pharmacological Sciences. 42 (10): 870–882. doi:10.1016/j.tips.2021.07.004. hdl: 10044/1/102175 . PMID   34446297. S2CID   237321716.
  2. ↑ Kruger, E. A.; Figg, W. D. (June 2000). "TNP-470: an angiogenesis inhibitor in clinical development for cancer". Expert Opinion on Investigational Drugs. 9 (6): 1383–1396. doi:10.1517/13543784.9.6.1383. ISSN   1354-3784. PMID   11060750. S2CID   45149960.
  3. ↑ Stadler, Walter M.; Kuzel, Timothy; Shapiro, Charles; Sosman, Jeffery; Clark, Joseph; Vogelzang, Nicholas J. (August 1999). "Multi-Institutional Study of the Angiogenesis Inhibitor TNP-470 in Metastatic Renal Carcinoma" . Journal of Clinical Oncology. 17 (8): 2541–2545. doi:10.1200/JCO.1999.17.8.2541. ISSN   0732-183X. PMID   10561320.
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