TNP-470

TNP-470
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
CAS Number	129298-91-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:90748;
ChEMBL	ChEMBL424278;
ChemSpider	328427;
DrugBank	DB08633;
ECHA InfoCard	100.189.666
EC Number	663-348-8;
PubChem CID	369976;
UNII	X47GR46481;
CompTox Dashboard (EPA)	DTXSID0041141 ;
	InChI 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;
	SMILES 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
Chemical formula	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). Infobox references

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

^ 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.
^ 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.
^ 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.