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
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
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15100281Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15100281
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.
Originator
Sources: https://worldwide.espacenet.com/publicationDetails/biblio?CC=EP&FT=D&NR=0130679B1&KC=B1
Curator's Comment: David W. Rasnick
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3178145 |
|||
Target ID: CHEMBL3837 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2671722 |
|||
Target ID: CHEMBL2225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9923616 |
|||
Target ID: CHEMBL4801 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9923616 |
|||
Target ID: CHEMBL4884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12657720 |
6.15 µM [IC50] | ||
Target ID: CHEMBL2334 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12657720 |
15.41 µM [IC50] | ||
Target ID: CHEMBL3308 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12657720 |
32.45 µM [IC50] | ||
Target ID: CHEMBL3468 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12657720 |
9.08 µM [IC50] | ||
Target ID: CHEMBL2273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12657720 |
110.7 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20128771
8 mg/kg in 10% dimethyl sulphoxide
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25915766
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
Edited
Tue Apr 01 16:29:23 GMT 2025
by
admin
on
Tue Apr 01 16:29:23 GMT 2025
|
| Record UNII |
34O3P3306Z
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
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
|
PRIMARY | |||
|
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 | |||
|
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 | |||
|
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 |