Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C34H63N5O9 |
| Molecular Weight | 685.8921 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CC(C)C)C(C)C)C(C)C)[C@@H](O)CC(O)=O
InChI
InChIKey=FAXGPCHRFPCXOO-LXTPJMTPSA-N
InChI=1S/C34H63N5O9/c1-17(2)12-23(37-33(47)31(21(9)10)39-34(48)30(20(7)8)38-27(42)14-19(5)6)25(40)15-28(43)35-22(11)32(46)36-24(13-18(3)4)26(41)16-29(44)45/h17-26,30-31,40-41H,12-16H2,1-11H3,(H,35,43)(H,36,46)(H,37,47)(H,38,42)(H,39,48)(H,44,45)/t22-,23-,24-,25-,26-,30-,31-/m0/s1
Pepstatin is a pentapeptide of microbial origin. The peptide inhibits the acid proteases pepsin and cathepsin D and the pressor enzyme renin. Pepstatin was shown to provide long-lasting inhibition (3 to 6 days) of cathepsin D in vivo in non-tumor bearers particularly in spleen, liver, kidney, lung, and heart. Pepstatin may prove useful as "anticachexia" agent by decreasing proteolysis in muscle and other tissues. The in vivo pepstatin and IL-2 treatment decreased the T-cells and increased the natural killer-like LAK precursor cells, possibly also with an increase in its activity, which were further induced by in vitro IL-2 culture to generate an augmented LAK cell activity. This suggests the clinical potential of pepstatin in IL-2-related immunotherapy. In rats injected centrally with the specific cathepsin D inhibitor, pepstatin, the protease activity was inhibited up to 90% in most brain regions.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2714 |
1.0 nM [Ki] | ||
Target ID: CHEMBL2581 |
0.5 nM [Kd] | ||
Target ID: CHEMBL286 |
0.13 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Endothelial tubulogenesis within fibrin gels specifically requires the activity of membrane-type-matrix metalloproteinases (MT-MMPs). | 2002-09-01 |
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| Linear non-competitive inhibition of solubilized human gamma-secretase by pepstatin A methylester, L685458, sulfonamides, and benzodiazepines. | 2002-08-30 |
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| Novel inhibition of porcine pepsin by a substituted piperidine. Preference for one of the enzyme conformers. | 2002-08-09 |
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| Combinatorial diversity of fission yeast SCF ubiquitin ligases by homo- and heterooligomeric assemblies of the F-box proteins Pop1p and Pop2p. | 2002-08-07 |
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| Aspartic proteinase in Dugesia tigrina (Girard) planaria. | 2002-07-23 |
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| Correlation between beta-amyloid peptide production and human APP-induced neuronal death. | 2002-07 |
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| Microinjection of cathepsin d induces caspase-dependent apoptosis in fibroblasts. | 2002-07 |
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| Enzymes with gelatinolytic activity can be found in Tityus bahiensis and Tityus serrulatus venoms. | 2002-07 |
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| Probing the importance and potential roles of the binding of the PH-domain protein Boi1 to acidic phospholipids. | 2002-06-27 |
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| Complexity of agonist- and cyclic AMP-mediated downregulation of the human beta 1-adrenergic receptor: role of internalization, degradation, and mRNA destabilization. | 2002-06-25 |
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| Implication of mitochondria-derived ROS and cardiolipin peroxidation in N-(4-hydroxyphenyl)retinamide-induced apoptosis. | 2002-06-17 |
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| Purification and partial amino acid sequences of an esterase from tomato. | 2002-06 |
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| The regulation of protein synthesis and translation factors by CD3 and CD28 in human primary T lymphocytes. | 2002-05-17 |
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| Natural antisense RNA inhibits the expression of BCMA, a tumour necrosis factor receptor homologue. | 2002-04-18 |
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| Cdc5 influences phosphorylation of Net1 and disassembly of the RENT complex. | 2002-04-17 |
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| Mechanisms of nordihydroguaiaretic acid-induced growth inhibition and apoptosis in human cancer cells. | 2002-04-08 |
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| Phosphorothioate oligonucleotides, suramin and heparin inhibit DNA-dependent protein kinase activity. | 2002-04-08 |
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| Lens epithelial cell apoptosis and intracellular Ca2+ increase in the presence of xanthurenic acid. | 2002-04-05 |
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| A selective plasmin inhibitor, trans-aminomethylcyclohexanecarbonyl-L-(O-picolyl)tyrosine-octylamide (YO-2), induces thymocyte apoptosis. | 2002-04-01 |
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| FAD-linked mutations in presenilin 1 alter the length of Abeta peptides derived from betaAPP transmembrane domain mutants. | 2002-03-16 |
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| Endosomal proteolysis of internalized insulin at the C-terminal region of the B chain by cathepsin D. | 2002-03-15 |
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| Auto-protective redox buffering systems in stimulated macrophages. | 2002-03-12 |
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| Endoproteolysis of presenilin in vitro: inhibition by gamma-secretase inhibitors. | 2002-03-12 |
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| Decreased apoptotic response of inclusion-cell disease fibroblasts: a consequence of lysosomal enzyme missorting? | 2002-03-10 |
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| Imidazoline drugs stabilize lysosomes and inhibit oxidative cytotoxicity in astrocytes. | 2002-03-01 |
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| Role of Ca2+-dependent metalloprotease-2 in stimulating Ca2+ ATPase activity under peroxynitrite treatment in bovine pulmonary artery smooth muscle membrane. | 2002-03 |
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| Overexpression, purification, and partial characterization of Saccharomyces cerevisiae processing alpha glucosidase I. | 2002-03 |
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| Lysosomal proteases as potential targets for the induction of apoptotic cell death in human neuroblastomas. | 2002-02-20 |
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| Involvement of cathepsin E in exogenous antigen processing in primary cultured murine microglia. | 2002-02-15 |
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| Mxi1 inhibits the proliferation of U87 glioma cells through down-regulation of cyclin B1 gene expression. | 2002-02-01 |
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| Src tyrosine kinase augments taxotere-induced apoptosis through enhanced expression and phosphorylation of Bcl-2. | 2002-02-01 |
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| Pepsinogens, progastricsins, and prochymosins: structure, function, evolution, and development. | 2002-02 |
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| Absorption, transportation and digestion of egg white in quail embryos. | 2002-02 |
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| Molecular cloning of an extracellular aspartic proteinase from Rhizopus microsporus and evidence for its expression during infection. | 2002-02 |
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| Free-energy analysis of enzyme-inhibitor binding: aspartic proteinase-pepstatin complexes. | 2002-01-11 |
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| Cell-associated collagenolytic activity by Candida albicans. | 2002 |
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| Altered prostanoid production by fibroblasts cultured from the lungs of human subjects with idiopathic pulmonary fibrosis. | 2002 |
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| The farnesyl transferase inhibitor RPR-130401 does not alter radiation susceptibility in human tumor cells with a K-Ras mutation in spite of large changes in ploidy and lamin B distribution. | 2002 |
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| Ca2+-mediated activation of ERK in hepatocytes by norepinephrine and prostaglandin F2 alpha: role of calmodulin and Src kinases. | 2002 |
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| Cytokine-stimulated T cells induce macrophage IL-10 production dependent on phosphatidylinositol 3-kinase and p70S6K: implications for rheumatoid arthritis. | 2002 |
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| Pleureryn, a novel protease from fresh fruiting bodies of the edible mushroom Pleurotus eryngii. | 2001-12-07 |
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| Human muscle protein degradation in vitro by eosinophil cationic protein (ECP). | 2001-12 |
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| Cathepsin D cleaves aggrecan at unique sites within the interglobular domain and chondroitin sulfate attachment regions that are also cleaved when cartilage is maintained at acid pH. | 2001-12 |
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| Myocardial enzymatic activity of renin and cathepsin D before and after bilateral nephrectomy. | 2001-11 |
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| Corpuscles of Stannius secrete renin or an isorenin that regulates cardiovascular function in freshwater North American eels, Anguilla rostrata LeSueur. | 2001-11 |
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| Biochemical alteration of membrane-associated IL-6 RI (80-kDa) in adherent macrophages and vascular endothelium. | 2001-09 |
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| Molecular dynamics simulations of the three dimensional model of plasmepsin II-peptidic inhibitor complexes. | 2001 |
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| Reconstitution of licensed replication origins on Xenopus sperm nuclei using purified proteins. | 2001 |
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| Generation of choline for acetylcholine synthesis by phospholipase D isoforms. | 2001 |
|
| Cloning, expression and nuclear localization of human NPM3, a member of the nucleophosmin/nucleoplasmin family of nuclear chaperones. | 2001 |
Patents
Sample Use Guides
Pepstatin A was added to the culture medium at a final concentration of 10-4 M in 0.2% DMSO. Pepstatin A had no effects on growing HeLa cells that were not treated with IFN-gamma. Addition of pepstatin A to the IFN-gamma-treated DHFR-transfected cells inhibited, to some extent, the killing process, as reflected by the elevated values of neutral red dye uptake.
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NCI_THESAURUS |
C783
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V6Y2T27Q1U
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m8530
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7989
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100000082520
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PEPSTATIN
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247-600-0
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CHEMBL296588
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C031375
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26305-03-3
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5478883
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C96295
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272671
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ACTIVE MOIETY
