Z-FA-FMK

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
CAS Number	197855-65-5  Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL5271003
ChemSpider	108843
IUPHAR/BPS	11257
PubChem CID	122019 6915837
UNII	34O3P3306Z  Y
InChI InChI=1S/C21H23FN2O4/c1-15(19(25)13-22)23-20(26)18(12-16-8-4-2-5-9-16)24-21(27)28-14-17-10-6-3-7-11-17/h2-11,15,18H,12-14H2,1H3,(H,23,26)(H,24,27) Key: ASXVEBPEZMSPHB-UHFFFAOYSA-N Key: ASXVEBPEZMSPHB-PKHIMPSTSA-N
SMILES FCC(=O)C(NC(=O)C(NC(=O)OCc1ccccc1)Cc2ccccc2)C CC(C(=O)CF)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2
Properties
Chemical formula	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). Infobox references

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): 3827–3836. doi:10.4049/jimmunol.177.6.3827. PMID   16951345. S2CID   23419301.