Tanespimycin

Tanespimycin
Names
IUPAC name
[(3S,5S,6R,7S,8E,10R,11S,12E,14E)-21-(allylamino)-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-8,12,14,18,21-pentaen-10-yl] carbamate
Other names
17-N-Allylamino-17-demethoxygeldanamycin
17-AAG
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1 checkY
    Key: AYUNIORJHRXIBJ-TXHRRWQRSA-N checkY
  • InChI=1/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
    Key: AYUNIORJHRXIBJ-TXHRRWQRBY
  • NC(=O)O[C@H]1C(/C)=C/[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)C\C2=C(/NCC=C)C(=O)\C=C(\NC(=O)C(\C)=C\C=C/[C@@H]1OC)C2=O
  • C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCC=C)/C)OC)OC(=O)N)\C)C)O)OC
Properties
C31H43N3O8
Molar mass 585.698 g·mol−1
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 ?)

Tanespimycin (17-N-allylamino-17-demethoxygeldanamycin, 17-AAG) is a derivative of the antibiotic geldanamycin that is being studied in the treatment of cancer, specifically in younger patients with certain types of leukemia or solid tumors, especially kidney tumors.

It works by inhibiting Hsp90, which is expressed in those tumors.[1]

It belongs to the family of drugs called antitumor antibiotics.

  1. ^ Dimopoulos MA, Mitsiades CS, Anderson KC, Richardson PG (February 2011). "Tanespimycin as antitumor therapy". Clinical Lymphoma, Myeloma & Leukemia. 11 (1): 17–22. doi:10.3816/CLML.2011.n.002. PMID 21454186.