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Details

Stereochemistry EPIMERIC
Molecular Formula C21H23FN2O4
Molecular Weight 386.4167
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MDL-201053, (DL-ALANINE)-

SMILES

CC(NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2)C(=O)CF

InChI

InChIKey=ASXVEBPEZMSPHB-PKHIMPSTSA-N
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

HIDE SMILES / InChI

Molecular Formula C21H23FN2O4
Molecular Weight 386.4167
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Z-FA-FMK | https://www.ncbi.nlm.nih.gov/pubmed/20834102 | https://www.ncbi.nlm.nih.gov/pubmed/12657720 | https://www.ncbi.nlm.nih.gov/pubmed/16951345 | https://www.ncbi.nlm.nih.gov/pubmed/3178145

MDL-201053, (DL-ALANINE)- (Z-FA-FMK) is an irreversible inhibitor of cysteine proteases, such as cathepsin B, L, and S. The compound has also inhibitited papain and cruzain. Z-FA-FMK has been shown to selectively inhibit effector caspase-2, caspase-3, caspase-6, and caspase-7 without affecting initiator caspase-8 and caspase-10 while showing minimal toxicity to normal mammalian cells in vitro. Due to Z-FA-FMK's effector caspase specificity, the compound has been recorded to inhibit some forms of caspase mediated apoptosis. The compound has been observed to be an effective in time dependent inactivation of cathepsin B isozymes from a number of tissues. Studies show Cathepsin B-like activity plays a role in the cascade of proteolytic cartilage destruction. Z-FA-FMK is an inhibitor of cathepsin H. 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. Z-FA-FMK blocks not only NF-kappaB activation but inhibits, also, T cell blast formation, and prevents cells from entering and leaving the cell cycle revealing demonstrating immunosuppressive abilities. Z-FA-FMK is a very effective viral inhibitor that can prevent reovirus replication in vitro and reovirus-mediated myocarditis, as well as reovirus-mediated oncolysis, in vivo.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.15 µM [IC50]
15.41 µM [IC50]
32.45 µM [IC50]
9.08 µM [IC50]
110.7 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Cysteine proteinase activity in arthritic rat knee joints and the effects of a selective systemic inhibitor, Z-Phe-AlaCH2F.
1988-10
Visualization of time-dependent inactivation of human tumor cathepsin B isozymes by a peptidyl fluoromethyl ketone using a fluorescent print technique.
1988-07-01
Patents

Sample Use Guides

8 mg/kg in 10% dimethyl sulphoxide
Route of Administration: Intravenous
T cell proliferation induced by anti-CD3 was inhibited in a concentration-dependent manner by z-FA-FMK (IC50 ~50 μM).
Substance Class Chemical
Created
by admin
on Tue Apr 01 16:29:23 GMT 2025
Edited
by admin
on Tue Apr 01 16:29:23 GMT 2025
Record UNII
34O3P3306Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MDL-201053, (DL-ALANINE)-
Common Name English
BENZYLOXYCARBONYL-PHE-DL-ALA-FLUOROMETHYLKETONE
Preferred Name English
CARBAMIC ACID, (2-((3-FLUORO-1-METHYL-2-OXOPROPYL)AMINO)-2-OXO-1-(PHENYLMETHYL)ETHYL)-, PHENYLMETHYL ESTER, (1(S))-
Systematic Name English
Z-FA-FMK, (DL-A)-
Common Name English
CARBAMIC ACID, N-((1S)-2-((3-FLUORO-1-METHYL-2-OXOPROPYL)AMINO)-2-OXO-1-(PHENYLMETHYL)ETHYL)-, PHENYLMETHYL ESTER
Systematic Name English
Z-PHE-DL-ALA-FLUOROMETHYLKETONE
Common Name English
Code System Code Type Description
CAS
197855-65-5
Created by admin on Tue Apr 01 16:29:23 GMT 2025 , Edited by admin on Tue Apr 01 16:29:23 GMT 2025
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EPA CompTox
DTXSID701336087
Created by admin on Tue Apr 01 16:29:23 GMT 2025 , Edited by admin on Tue Apr 01 16:29:23 GMT 2025
PRIMARY
FDA UNII
34O3P3306Z
Created by admin on Tue Apr 01 16:29:23 GMT 2025 , Edited by admin on Tue Apr 01 16:29:23 GMT 2025
PRIMARY
PUBCHEM
6915837
Created by admin on Tue Apr 01 16:29:23 GMT 2025 , Edited by admin on Tue Apr 01 16:29:23 GMT 2025
PRIMARY