An inhibitor of cysteine proteases, including cathepsin B
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Alternative(s)
42444Z-FA-FMK
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Z-FA-FMK

Item No. 14462

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S)-2-[(3-fluoro-1-methyl-2-oxopropyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid, phenylmethyl ester
CAS Number
197855-65-5
Synonyms
  • Z-Phe-Ala-Fluoromethyl Ketone
Molecular Formula
C21H23FN2O4
Formula Weight
386.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/ml
SMILES
O=C(N[C@@H](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)/t15?,18-/m0/s1
InChi Key
ASXVEBPEZMSPHB-PKHIMPSTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $81

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    5 mg

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    Product Description

    Z-FA-FMK is an irreversible inhibitor of cysteine proteases, including cathepsins B, L, and S, cruzain, and papain.1 It also inhibits effector caspases-2, -3, -6, and -7 (IC50 = 6-32 µM) without affecting the initiator caspases-8 and -10.2 Z-FA-FMK also modulates infection by certain bacteria, parasites, and viruses.3,4,5 It can be used both in cells and in vivo.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ahmed, N.K., Martin, L.A., Watts, L.M., et al. Peptidyl fluoromethyl ketones as inhibitors of cathepsin B. Implication for treatment of rheumatoid arthritis. Biochem. Pharmacol. 44(6), 1201-1207 (1992).

    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. Harth, G., Andrews, N., Mills, A.A., et al. Peptide-fluoromethyl ketones arrest intracellular replication and intercellular transmission of Trypanosoma cruzi. Mol. Biochem. Parasitol. 58(1), 17-24 (1993).

    4. Lawrence, C.P., Kadioglu, A., Yang, A.L., et al. The cathepsin B inhibitor, z-FA-FMK, inhibits human T cell proliferation in vitro and modulates host response to pneumococcal infection in vivo. J. Immunol. 177(6), 3827-3836 (2006).

    5. Kim, M., Hansen, K.K., Davis, L., et al. Z-FA-FMK as a novel potent inhibitor of reovirus pathogenesis and oncolysis in vivo. Antivir.Ther. 15(6), 897-905 (2010).