Z-FA-FMK
Names
IUPAC name
N-[(1S)-2-[(3-Fluoro-1-methyl-2-oxopropyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-,phenylmethyl ester
Other names
Z-Phe-Ala-Fluoromethyl Ketone
Identifiers
3D model (JSmol)
UNII
  • FCC(=O)C(NC(=O)C(NC(=O)OCc1ccccc1)Cc2ccccc2)C
Properties
C21H23FN2O4
Molar mass 386.423 g·mol−1
Density 1.207 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Z-FA-FMK, abbreviating for benzyloxycarbonyl-phenylalanyl-alanyl-fluoromethyl ketone, is a very potent irreversible inhibitor of cysteine proteases, including cathepsins B, L, and S, cruzain, and papain. It also selectively inhibits effector caspases 2, 3, 6, and 7 but not caspases 8 and 10.[1] This compound has been shown to block the production of IL1-α, IL1-β, and TNF-α induced by LPS in macrophages by inhibiting NF-κB pathways.

References

  1. ^ Lawrence CP, et al. (15 September 2006). "The cathepsin B inhibitor, Z-FA-FMK, inhibits human T cell proliferation in vitro and modulates host response to pneumococcal infection in vivo". Journal of Immunology. 177 (6): 3827–36. doi:10.4049/jimmunol.177.6.3827. PMID 16951345. S2CID 23419301.


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