A cathepsin B inhibitor
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Alternative(s)
14462Z-FA-FMK
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Z-FA-FMK

Item No. 42444

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[2-[(3-fluoro-1-methyl-2-oxopropyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid, phenylmethyl ester
CAS Number
96922-64-4
Synonyms
  • Cathepsin B Inhibitor
  • Z-Phe-Ala-Fluoromethyl Ketone
Molecular Formula
C21H23FN2O4
Formula Weight
386.4
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
O=C(NC(CC1=CC=CC=C1)C(NC(C)C(CF)=O)=O)OCC2=CC=CC=C2
InChi Code
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)
InChi Key
ASXVEBPEZMSPHB-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $138

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    Product Description

    Z-FA-FMK is an inhibitor of cathepsin B (Ki = 1.5 µM).1 It also is an inhibitor of caspase-2, -3, -6, -7, and -9 (IC50 = 6.147, 15.41, 32.45, 9.077, and 110.7 µM, respectively).2 Z-FA-FMK inhibits severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) main protease (Mpro), also known as 3C-like protease (3CLpro), in a cell-free assay (IC50 = 11.39 µM).3 It inhibits SARS-CoV-2 replication in infected Vero E6 cells (EC50 = 0.13 µM) without inducing cytotoxicity in the same cells with a 50% cytotoxic concentration (CC50) value of >20 µM. Z-FA-FMK (50 µM) decreases the proliferation of, and levels of glutathione (GSH) in, and increases levels of reactive oxygen species (ROS) in anti-CD3-stimulated primary human peripheral blood mononuclear cells (PBMCs).4 It inhibits LPS-induced increases in levels of IL-1β in PU5-1.8 macrophages and Nf-κB transactivation in Mf4/4 macrophages when used at a concentration of 50 µM.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Smith, R.A., Copp, L.J., Donnelly, S.L., et al. Inhibition of cathepsin B by peptidyl aldehydes and ketones: Slow-binding behavior of a trifluoromethyl ketone. Biochemistry 27(17), 6568-6573 (1988).

    2. Lopez-Hernandez, F.J., Ortiz, M.A., Bayon, Y., et al. Z-FA-fmk inhibits effector caspases but not initiator caspases 8 and 10, and demonstrates that novel anticancer retinoid-related molecules induce apoptosis via the intrinsic pathway. Mol. Cancer Ther. 2(3), 255-263 (2003).

    3. Zhu, W., Xu, M., Chen, C.Z., et al. Identification of SARS-CoV-2 3CL protease inhibitors by a quantitative high-throughput screening. ACS Pharmacol. Transl. Sci. 3(5), 1008-1016 (2020).

    4. Rajah, T., and Chow, S.C. Suppression of human T cell proliferation mediated by the cathepsin B inhibitor, z-FA-FMK is due to oxidative stress. PLoS One 10(4), e0123711 (2015).

    5. Schotte, P., Schauvliege, R., Janssens, S., et al. The cathepsin B inhibitor z-FA.fmk inhibits cytokine production in macrophages stimulated by lipopolysaccharide. The Journal of Biological Chemisty 276(24), 21153-21157 (2001).