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Tanespimycin

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(Redirected from 17-N-allylamino-17-demethoxygeldanamycin)

Tanespimycin
Names
IUPAC name docosa-8,12,14,18,21-pentaen-10-yl] carbamate
Other names 17-N-Allylamino-17-demethoxygeldanamycin
17-AAG
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
IUPHAR/BPS
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: AYUNIORJHRXIBJ-TXHRRWQRSA-N
  • 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/s1Key: AYUNIORJHRXIBJ-TXHRRWQRBY
SMILES
  • NC(=O)O1C(/C)=C/(C)(O)(OC)C(C)C\C2=C(/NCC=C)C(=O)\C=C(\NC(=O)C(\C)=C\C=C/1OC)C2=O
  • C1C(((/C=C(/((/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 585.698 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

It belongs to the family of drugs called antitumor antibiotics.

Clinical trials

Bristol-Myers Squibb conducted Phase 1 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.

References

  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.
  2. Clinical trial number NCT00093821 for "Phase 1 trial: 17-N-Allylamino-17-Demethoxygeldanamycin (17-AAG) in Treating Young Patients With Recurrent or Refractory Leukemia or Solid Tumors" at ClinicalTrials.gov
  3. Clinical trial number NCT00079404 for "Phase 1 trial: 17-N-Allylamino-17-Demethoxygeldanamycin in Treating Young Patients With Relapsed or Refractory Solid Tumors or Leukemia" at ClinicalTrials.gov
  4. "Bristol-Myers Squibb Halts Development of Tanespimycin". The Myeloma Beacon. 22 July 2010. Archived from the original on 28 December 2010.

External links

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