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ChemicalBook--->CAS DataBase List--->747412-49-3

747412-49-3

747412-49-3 Structure

747412-49-3 Structure
IdentificationBack Directory
[Name]

5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide
[CAS]

747412-49-3
[Synonyms]

AUY 922
VER 52296
VER-52296
LuMinespib
NVP-AUY922
AUY922, VER-52296
NVP-AUY922, >=98%
AUY922 (NVP-AUY922)
Luminespib (NVP-AUY922)
AUY922,NVP-AUY-922,Luminespib
NVP-AUY922, Luminespib, VER52296
Luminespib (AUY-922, NVP-AUY922)
5-(2,4-Dihydroxy-5-isopropylphenyl)-N-ethyl-4-(4-(morpholinomethyl)phenyl)isoxazole-3-carboxam
5-(2,4-dihydroxy-5-isopropylphenyl)-N-ethyl-4-(4-(morpholinomethyl)phenyl)isoxazole-3-carboxamide
5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide
5-[2,4-Dihydroxy-5-isopropylphenyl]-N-ethyl-4-[4-(4-morpholinylmethyl)phenyl]-3-isoxazolecarboxamide AUY922 (NVP-AUY922)
[Molecular Formula]

C26H31N3O5
[MDL Number]

MFCD14635361
[MOL File]

747412-49-3.mol
[Molecular Weight]

465.547
Chemical PropertiesBack Directory
[Melting point ]

180-184°C
[Boiling point ]

640.1±55.0 °C(Predicted)
[density ]

1.234
[storage temp. ]

-20°C
[solubility ]

Soluble in DMSO (>25 mg/ml)
[form ]

solid
[pka]

8.47±0.48(Predicted)
[color ]

White
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
[CAS DataBase Reference]

747412-49-3
Hazard InformationBack Directory
[Uses]

NVP-AUY 922 is a potent inhibitor of heat shock protein 90 (Hsp90) that prevents the proliferation of a range of human cancer cell lines. NVP-AUY 922 has been shown to enhance the radiation sensitivity of tumor cell lines under hypoxia.
[Definition]

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-(2,4-dihydroxy-5-isopropylphenyl)-4-[4-(morpholin-4-ylmethyl)phenyl]-1,2-oxazole-3-carboxylic acid with the amino group of ethylamine.
[target]

HSP90α
[storage]

Store at -20°C
[References]

Brough et al. (2008), 4,5-Diarylisoxazole Hsp90 chaperone inhibitors: potential therapeutic agents for the treatment of cancer; Med. Chem. 51 196 Eccles et al. (2008), NVP-AUY922: a novel heat shock protein 90 inhibitor active against xenograft tumor growth, angiogenesis, and metastasis; Cancer Res. 68 2850 Massey et al. (2010), Preclinical antitumor activity of the orally available heat shock protein 90 inhibitor; Cancer Ther. 5 1807 Song et al. (2020), HSP90A inhibition promotes anti-tumor immunity by reversing multi-modal resistance and stem-like property of immune-refractory tumors; Commun. 11 562 Schwab and Multhoff (2022), A Low Membrane Hsp70 Expression in Tumor Cells With Impaired Lactate Metabolism Mediates Radiosensitization by NVP-AUY922; Oncol. 12 861266 Djuzenova et al. (2012), Hsp90 inhibitor NVP-AUY922 enhances radiation sensitivity of tumor cells lines under hypoxia; Cancer Biol. Ther. 13 425 Schilling et al. (2015), Sensitizing tumor cells to radiation by targeting the heat shock response; Cancer Lett. 360 294
Safety DataBack Directory
[HS Code ]

2934999090
Questions And AnswerBack Directory
[Description]

Luminespib (AUY-922, NVP-AUY922) is a highly potent HSP90 inhibitor for HSP90α/β with IC50 of 13 nM /21 nM in cell-free assays, weaker potency against the HSP90 family members GRP94 and TRAP-1, exhibits the tightest binding of any small-molecule HSP90 ligand. Phase 2.
[In vitro]

NVP-AUY922 inhibits proliferation of various human cancer cell lines in vitro, with an average GI50 of 9 nM. The IC50 values of NVP-AUY922 fall in the range of 2 to 40 nM in these gastric cancer cell lines. IC50 value for the BEAS-2B cells is 28.49 nM. Treatment with NVP-AUY922 does not influence the expression of HSP90, but expression of HSP70 gets elevated by NVP-AUY922 treatment. NVP-AUY922 increases the binding of HSP70 to HSP90. NVP-AUY922 causes p23 dissociation from the HSP90 complex and can then recruit HSP70 to the HSP90 complex. After the treatment with NVP-AUY922, expression of receptor tyrosine kinases including VEGFR1, 2, 3 and PDGFRɑ is decreased. A decrease is also noticed in the expression of Akt and phospho-Akt. Meanwhile, treatment with NVP-AUY922 causes decreased expression of HER-2 in NCI-N87 cells. NVP-AUY922 treatment results in binding of HSP90 to client proteins and setting them up as targets for degradation by the proteasome. NVP-AUY922 can influence cell growth by affecting multiple signaling pathways. In addition, treatment with the proteasome inhibitor, MG132, restores expression of thymidylate synthase, which is decreased by NVP-AUY922. NVP-AUY922 increases the expression of cleaved caspase-3 leading to apoptosis in HSC-2 cells.
[In vivo]

Treatment with NVP-AUY922 causes a robust antitumor response and inhibits p-Akt and VEGF expression in an HSC-2 xenograft model. In BT474, NVP-AUY922 shows complete loss of ERBB2 and substantial depletion of ERα, in addition to reductions in CDK4 and phospho-ERK1/2.
Spectrum DetailBack Directory
[Spectrum Detail]

Luminespib(747412-49-3)1HNMR
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