Synonym
(S)-Z-FA-FMK; Z-FA-fluoromethyl ketone
IUPAC/Chemical Name
N-[(1S)-2-[(3-fluoro-1-methyl-2-oxopropyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid, phenylmethyl ester
InChi Key
ASXVEBPEZMSPHB-YJBOKZPZSA-N
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
SMILES Code
O=C(OCC1=CC=CC=C1)N[C@@H](CC2=CC=CC=C2)C(NC(C)C(CF)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
386.42
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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. Biochemical Pharmacology 44, 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. Molecular Cancer Therapeutics 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. Molecular and Biochemical Parasitology 58, 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. Journal of Immunology 177, 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).
-Z-FA-FMK5656.jpg "(S)-Z-FA-FMK")
