NVP-AUY922

NVP-AUY922

Names
IUPAC name 5-(2,4-Dihydroxy-5-isopropyl-phenyl)-N-ethyl-4-[4-(morpholinomethyl)phenyl]isoxazole-3-carboxamide
Other names NVP-AUY-922; AUY922; VER-52296
Identifiers
CAS Number	747412-49-3
ChEBI	CHEBI:83656
ChEMBL	ChEMBL252164
ChemSpider	21377936
Jmol interactive 3D	Image
InChI InChI=1S/C26H31N3O5/c1-4-27-26(32)24-23(18-7-5-17(6-8-18)15-29-9-11-33-12-10-29)25(34-28-24)20-13-19(16(2)3)21(30)14-22(20)31/h5-8,13-14,16,30-31H,4,9-12,15H2,1-3H3,(H,27,32) Key: NDAZATDQFDPQBD-UHFFFAOYSA-N InChI=1S/C26H31N3O5/c1-4-27-26(32)24-23(18-7-5-17(6-8-18)15-29-9-11-33-12-10-29)25(34-28-24)20-13-19(16(2)3)21(30)14-22(20)31/h5-8,13-14,16,30-31H,4,9-12,15H2,1-3H3,(H,27,32)
SMILES CC(C)c1cc(c(O)cc1O)c2onc(C(=O)NCC)c2c3ccc(cc3)CN4CCOCC4
Properties
Chemical formula	C26H31N3O5
Molar mass	465.55 g·mol^−1
Appearance	Colorless solid[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

NVP-AUY922 is an experimental drug candidate for the treatment of cancer. It was discovered through a collaboration between The Institute of Cancer Research and the pharmaceutical company Vernalis^[2] and licensed to Novartis.^[3] It is currently in Phase II clinical trials.^[4]

NVP-AUY922 is an inhibitor of heat shock protein 90 (Hsp90),^[1] which is a chaperone protein that plays a role in the modification of a variety of proteins that have been implicated in oncogenesis. NVP-AUY922 has shown promising activity in preclinical testing against several different tumor types.^[5][6][7][8]

See also

• Hsp90 inhibitors

References

1. Brough, Paul A.; Aherne, Wynne; Barril, Xavier; Borgognoni, Jenifer; Boxall, Kathy; Cansfield, Julie E.; Cheung, Kwai-Ming J.; Collins, Ian; Davies, Nicholas G. M. (2008). "4,5-Diarylisoxazole Hsp90 Chaperone Inhibitors: Potential Therapeutic Agents for the Treatment of Cancer". Journal of Medicinal Chemistry 51 (2): 196–218. doi:10.1021/jm701018h. PMID 18020435.
2. "Structure-based design of cancer therapeutics" (PDF). The Institute of Cancer Research.
3. "AUY922". Vernalis.
4. "Small caps: Vernalis drug fillip". Financial Times. July 19, 2011.
5. Jensen, Michael; Schoepfer, Joseph; Radimerski, Thomas; Massey, Andrew; Guy, Chantale T; Brueggen, Josef; Quadt, Cornelia; Buckler, Alan; Cozens, Robert (2008). "NVP-AUY922: a small molecule HSP90 inhibitor with potent antitumor activity in preclinical breast cancer models". Breast Cancer Research 10 (2): R33. doi:10.1186/bcr1996. PMC 2397535. PMID 18430202.
6. Gaspar, N.; Sharp, S. Y.; Eccles, S. A.; Gowan, S.; Popov, S.; Jones, C.; Pearson, A.; Vassal, G.; Workman, P. (2010). "Mechanistic Evaluation of the Novel HSP90 Inhibitor NVP-AUY922 in Adult and Pediatric Glioblastoma". Molecular Cancer Therapeutics 9 (5): 1219–1233. doi:10.1158/1535-7163.MCT-09-0683. PMC 2875164. PMID 20457619.
7. Okui, T; Shimo, T; Hassan, NM; Fukazawa, T; Kurio, N; Takaoka, M; Naomoto, Y; Sasaki, A (2011). "Antitumor effect of novel HSP90 inhibitor NVP-AUY922 against oral squamous cell carcinoma". Anticancer research 31 (4): 1197–204. PMID 21508365.
8. Eccles, S. A.; Massey, A.; Raynaud, F. I.; Sharp, S. Y.; Box, G.; Valenti, M.; Patterson, L.; De Haven Brandon, A.; Gowan, S. (2008). "NVP-AUY922: A Novel Heat Shock Protein 90 Inhibitor Active against Xenograft Tumor Growth, Angiogenesis, and Metastasis". Cancer Research 68 (8): 2850–2860. doi:10.1158/0008-5472.CAN-07-5256. PMID 18413753.