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Avagacestat (BMS-708163) — Datasheet

CAT. NO. DC3114

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ParameterValue
Chemical NameAvagacestat
CAS No.1146699-66-2
Synonyms(R)-2-(4-Chloro-N-(2-fluoro-4-(1,2,4-oxadiazol-3-yl)benzyl)phenylsulfonamido)-5,5,5-trifluoropentanamide;BMS-708163;Avagacestat (BMS-708163);(2R)-2-[(4-chlorophenyl)sulfonyl-[[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoropentanamide;(R)-2-(4-Chloro-N-(2-fluoro-4-(1,2,4-oxadiazol-3-yl)benzyl)-phenylsulfonamido)-5,5,5-trifluoropentanamide;(R)-2-[[4-chlorophenyl)sulfonyl][[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoropentanamide;Avagacestat;BMS-708163 (avagacestat);Pentanamide, 2-[[(4-chlorophenyl)sulfonyl][[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoro-, (2R)-;BMS708163;(2R)-2-[N-[(4-Chlorophenyl)sulfonyl]-N-[[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoropentanamide;(2R)-2-[N-[(4-Chlorophenyl)sulfonyl]-N-[2-fluoro-4-(1,2,4-oxadiazol-3-yl)benzyl]amino]-5,5,5-trifluoropentanamide;BMS 708163;TQ44WWY45Q;(2R)-2-[(4-Chlorophenyl)sulfonyl-[[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoro-pentanamide;(2R)-5,5,5-trifluoro-2-(N-;(2R)-5,5,5-trifluoro-2-(N-{[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl}4-chlorobenzenesulfonamido)pentanamide;(2R)-2-[(4-Chlorophenyl)sulfo;BMS-708163-01;EX-A2871;BDBM50458169;D09869;(2R)-2-[(4-chlorophenyl)sulonyl-[[2-luoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-triluoropentanamide;AKOS005146523;MFCD13195458;(R)-2-((4-Chloro-N-(2-fluoro-4-(1,2,4-oxadiazol-3-yl)benzyl)phenyl)sulfonamido)-5,5,5-trifluoropentanamide;PENTANAMIDE, 2-(((4-CHLOROPHENYL)SULFONYL)((2-FLUORO-4-(1,2,4-OXADIAZOL-3-YL)PHENYL)METHYL)AMINO)-5,5,5-TRIFLUORO-, (2R)-;BCPP000327;HMS3884O07;SW218162-2;C71464;DB11893;1146699-66-2;UNII-TQ44WWY45Q;AKOS016016280;s1262;CHEMBL1090771;CCG-269860;(2R)-2-[[(4-Chlorophenyl)sulfonyl][[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoro-pentanamide;BCP9000429;AVAGACESTAT [WHO-DD];SCHEMBL310019;Avagacestat; BMS-708163;CHEBI:177493;Avagacestat (USAN);(2R)-2-[[(4-Chlorophenyl)sulfonyl][[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-trifluoropentanamide;BCP01770;GTPL6489;(2R)-2-[(4-chlorophenyl)sulfonyl-[[2-fluoranyl-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]amino]-5,5,5-tris(fluoranyl)pentanamide;MRF-0000009;DTXSID40150811;Avagacestat [USAN];MLS006011074;A894166;Avagacestat, >=98% (HPLC);NSC-761217;SMR004676648;HY-50845;EN9;AVAGACESTAT [INN];AS-75078;BMS-708163;(R)-2-(4-chloro-N-(2-fluoro-4-(1,2,4-oxadiazol-3-yl)benzyl)phenylsulfonamido)-5,5,5-trifluoropentanamide;Avagacestat [USAN:INN];BMS-70816301;NCGC00346504-01;NS00072555;Q27074630;(2R)-2-(N-((4-Chlorophenyl)sulfonyl)-N-((2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl)methyl)amino)-5,5,5-trifluoropentanamide;BCP0726000124;CS-0180;NSC761217;(2R)-5,5,5-trifluoro-2-(N-((2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl)methyl)4-chlorobenzenesulfonamido)pentanamide;BRD-K83720053-001-03-8;N~2~-[(4-chlorophenyl)sulfonyl]-5,5,...
FormulaC20H17ClF4N4O4S
M.Wt520.884996175766
SMILESClC1C=CC(=CC=1)S(N(CC1C=CC(C2=NOC=N2)=CC=1F)[C@@H](C(N)=O)CCC(F)(F)F)(=O)=O
Purity>98%
Storage2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO

Biological Activity

BMS-708163 is a potent inhibitor of γ-secretase, with IC50s of 0.27 nM and 0.30 nM for Aβ42 and Aβ40 inhibition; BMS-708163 also inhibits NICD (Notch IntraCellular Domain) with IC50 of 0.84 nM and shows weak inhibition of CYP2C19, with IC50 of 20 μM.

In Vitro

IC50: 0.27 nM (γ-secretase, Aβ42), 0.30 nM (γ-secretase, Aβ40), 20 μM (CYP2C19)[1], 0.84 nM (NICD)[2]

In Vivo

BMS-708163 significantly reduces both plasma and brain Aβ40 levels relative to control at 10 and 100 mg/kg for the entire dosing interval, demonstrates significant Aβ40 lowering for 8 h after an oral dose of 1 mg/kg, and significantly lowers CSF Aβ40 levels in rats, when measured 5 h after single oral doses ranging from 3 to 100 mg/kg[1]. BMS-708163 (10 mg/kg) monotherapy has a minor inhibitory effect on PC9/AB2 tumor growth compared with gefitinib alone. BMS-708163 monotherapy results in a slight increase in caspase 3 expression as well as a mild decrease in Ki-67 expression in vivo. In the xenograft lung cancer samples treated with BMS-708163 plus gefitinib, there are a marked increase in caspase 3 expression and a reduction in Ki-67 staining[3].

References & source

DC Chemicals original product information

Published experimental findings depend on the model and assay conditions. They do not guarantee equivalent performance in every application. For laboratory research use only.

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