17-N-Allylamino-17-demethoxygeldanamycin

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
CAS Number	75747-14-7^N
ChEMBL	ChEMBL109480^Y
ChemSpider	21106220^Y
IUPHAR/BPS	7751
Jmol interactive 3D	Image Image
PubChem	6440175
UNII	4GY0AVT3L4^Y
InChI 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^Y Key: AYUNIORJHRXIBJ-TXHRRWQRSA-N^Y 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
SMILES 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
Chemical formula	C₃₁H₄₃N₃O₈
Molar mass	585.70 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 ^YN ?)
Infobox references

Tanespimycin (17-N-allylamino-17-demethoxygeldanamycin, 17-AAG) is a derivative of the antibiotic geldanamycin that is being studied in the treatment of cancer, specific young 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.

Clinical trials

Tanespimycin Bristol-Myers Squibb conducted Phase 1^[2]^[3] and Phase 2 clinical trials. However, in 2010 the company halted development of tanespimycin, during late-stage clinical trials as a potential treatment for multiple myeloma. While no definitive explanation was given, it has been suggested that Bristol-Myers Squibb halted development over concerns of the financial feasibility of tanespimycin development given the 2014 expiry of the patent on this compound, and the relative expense of manufacture.^[4]

References

↑ Dimopoulos, MA; Mitsiades, CS; Anderson, KC; Richardson, PG (2011). "Tanespimycin as antitumor therapy". Clinical lymphoma, myeloma & leukemia 11 (1): 17–22. doi:10.3816/CLML.2011.n.002. PMID 21454186.
↑ http://www.clinicaltrials.gov/ct/show/NCT00093821 Phase 1 trial: 17-N-Allylamino-17-Demethoxygeldanamycin (17-AAG) in Treating Young Patients With Recurrent or Refractory Leukemia or Solid Tumors
↑ http://www.clinicaltrials.gov/ct/show/NCT00079404 Phase 1 trial : 17-N-Allylamino-17-Demethoxygeldanamycin in Treating Young Patients With Relapsed or Refractory Solid Tumors or Leukemia
↑

External links

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