Ganetespib (STA-9090)

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WARNING: This product is for research use only, not for human or veterinary use.

Description:Ganetespib, also known as STA-9090, is a synthetic small-molecule inhibitor of heat shock protein 90 (Hsp90) with potential antineoplastic activity. Hsp90 inhibitor STA-9090 binds to and inhibits Hsp90, resulting in the proteasomal degradation of oncogenic client proteins, the inhibition of cell proliferation and the elevation of heat shock protein 72 (Hsp72); it may inhibit the activity of multiple kinases, such as c-Kit, EGFR, and Bcr-Abl, which as client proteins depend on functional HsP90 for maintenance.

Price and Availability

Ganetespib (STA-9090), purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 202703Name: Ganetespib (STA-9090)CAS#: 888216-25-9Chemical Formula: C20H20N4O3Exact Mass: 364.15354Molecular Weight: 364.4Elemental Analysis:C, 65.92; H, 5.53; N, 15.38; O, 13.17

Synonym:STA9090; STA 9090; STA-9090; Ganetespib

IUPAC/Chemical Name:5-[2,4-dihydroxy-5-(1-methylethyl)phenyl]-4-(1-methyl-1H-indol-5-yl)-2,4-dihydro-3H- 1,2,4-triazol-3-one

InChi Key:RVAQIUULWULRNW-UHFFFAOYSA-N

InChi Code:InChI=1S/C20H20N4O3/c1-11(2)14-9-15(18(26)10-17(14)25)19-21-22-20(27)24(19)13-4-5-16-12(8-13)6-7-23(16)3/h4-11,25-26H,1-3H3,(H,22,27)

SMILES Code:O=C1NN=C(C2=CC(C(C)C)=C(O)C=C2O)N1C3=CC4=C(N(C)C=C4)C=C3

Technical Data

References

1: Xiang L, Gilkes DM, Chaturvedi P, Luo W, Hu H,Takano N, Liang H, Semenza GL. Ganetespib blocks HIF-1 activity andinhibits tumor growth, vascularization, stem cell maintenance, invasion,and metastasis in orthotopic mouse models of triple-negative breastcancer. J Mol Med (Berl). 2013 Nov 20. [Epub ahead of print] PubMedPMID: 24248265.

2: Proia DA, Zhang C, Sequeira M, Jimenez JP, He S, Spector NL, ShapiroGI, Tolaney S, Nagai M, Acquaviva J, Smith DL, Sang J, Bates RC, El-HariryI. Preclinical activity profile and therapeutic efficacy of the Hsp90inhibitor ganetespib in triple-negative breast cancer. Clin Cancer Res.2013 Oct 30. [Epub ahead of print] PubMed PMID: 24173541.

3: Lai CH, Park KS, Lee DH, Alberobello AT, Raffeld M, Pierobon M, PinE, Petricoin Iii EF, Wang Y, Giaccone G. HSP-90 inhibitor ganetespib issynergistic with doxorubicin in small cell lung cancer. Oncogene. 2013Oct 28. doi: 10.1038/onc.2013.439. [Epub ahead of print] PubMed PMID:24166505.

4: Miyajima N, Tsutsumi S, Sourbier C, Beebe K, Mollapour M, Rivas C,Yoshida S, Trepel JB, Huang Y, Tatokoro M, Shinohara N, Nonomura K,Neckers L. The HSP90 Inhibitor Ganetespib Synergizes with the MET KinaseInhibitor Crizotinib in both Crizotinib-Sensitive and -ResistantMET-Driven Tumor Models. Cancer Res. 2013 Dec 1;73(23):7022-33. doi:10.1158/0008-5472.CAN-13-1156. Epub 2013 Oct 11. PubMed PMID: 24121490.

5: Ganetespib AIDS lung cancer survival. Cancer Discov. 2013Jul;3(7):OF7. doi: 10.1158/2159-8290.CD-NB2013-085. Epub 2013 Jun 6.PubMed PMID: 23847382.

6: Nagaraju GP, Park W, Wen J, Mahaseth H, Landry J, Farris AB,Willingham F, Sullivan PS, Proia DA, El-Hariry I, Taliaferro-Smith L,Diaz R, El-Rayes BF. Antiangiogenic effects of ganetespib in colorectalcancer mediated through inhibition of HIF-1α and STAT-3. Angiogenesis.2013 Oct;16(4):903-17. doi: 10.1007/s10456-013-9364-7. Epub 2013 Jul 10.Erratum in: Angiogenesis. 2013 Oct;16(4):919. Ganji, PurnachandraNagaraju [corrected to Nagaraju, Ganji Purnachandra]. PubMed PMID:23838996.

7: Friedland JC, Smith DL, Sang J, Acquaviva J, He S, Zhang C, Proia DA.Targeted inhibition of Hsp90 by ganetespib is effective across a broadspectrum of breast cancer subtypes. Invest New Drugs. 2013 May 18. [Epubahead of print] PubMed PMID: 23686707.

8: Socinski MA, Goldman J, El-Hariry I, Koczywas M, Vukovic V, Horn L,Paschold E, Salgia R, West H, Sequist LV, Bonomi P, Brahmer J, Chen LC,Sandler A, Belani CP, Webb T, Harper H, Huberman M, Ramalingam S, WongKK, Teofilovici F, Guo W, Shapiro GI. A multicenter phase II study ofganetespib monotherapy in patients with genotypically defined advancednon-small cell lung cancer. Clin Cancer Res. 2013 Jun 1;19(11):3068-77.doi: 10.1158/1078-0432.CCR-12-3381. Epub 2013 Apr 3. PubMed PMID:23553849.

9: Goldman JW, Raju RN, Gordon GA, El-Hariry I, Teofilivici F, VukovicVM, Bradley R, Karol MD, Chen Y, Guo W, Inoue T, Rosen LS. A first inhuman, safety, pharmacokinetics, and clinical activity phase I study ofonce weekly administration of the Hsp90 inhibitor ganetespib (STA-9090)in patients with solid malignancies. BMC Cancer. 2013 Mar 25;13:152. doi:10.1186/1471-2407-13-152. PubMed PMID: 23530663; PubMed Central PMCID:PMC3626541.

10: Wu X, Marmarelis ME, Hodi FS. Activity of the heat shock protein 90inhibitor ganetespib in melanoma. PLoS One. 2013;8(2):e56134. doi:10.1371/journal.pone.0056134. Epub 2013 Feb 13. PubMed PMID: 23418523;PubMed Central PMCID: PMC3572008.