Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H30N2O4 |
| Molecular Weight | 362.4632 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1)C=O
InChI
InChIKey=PGGUOGKHUUUWAF-ROUUACIJSA-N
InChI=1S/C20H30N2O4/c1-4-5-11-17(13-23)21-19(24)18(12-15(2)3)22-20(25)26-14-16-9-7-6-8-10-16/h6-10,13,15,17-18H,4-5,11-12,14H2,1-3H3,(H,21,24)(H,22,25)/t17-,18-/m0/s1
| Molecular Formula | C20H30N2O4 |
| Molecular Weight | 362.4632 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Сalpeptin is useful cell-penetrative calpain inhibitor. Calpeptin inhibits the cell growth of ER (estrogen receptor) positive breast cancer cells, such as MCF-7, T-47D, and ZR-75-1 in the presence of Estradiol. Studies in rodent and cell culture models of Parkinson's disease suggest that treatment with calpain inhibitor calpeptin can prevent neuronal death and restore functions. The combination of histone deacetylase inhibitors and calpeptin inhibited the growth of two distinctly different types of breast cancer cells and could have wide clinical applications. Calpeptin is a promising antitumor agent for pancreatic cancer.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2111357 |
0.04 µM [IC50] | ||
Target ID: CHEMBL4143 |
0.034 µM [IC50] | ||
Target ID: CHEMBL2176800 |
|||
Target ID: CHEMBL2305 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Calpain inhibitor calpeptin suppresses pancreatic cancer by disrupting cancer-stromal interactions in a mouse xenograft model. | 2016-10 |
|
| Amelioration of cisplatin-induced experimental peripheral neuropathy by a small molecule targeting p75 NTR. | 2014-12 |
|
| Anti-breast cancer effects of histone deacetylase inhibitors and calpain inhibitor. | 2012-07 |
|
| Distinct regulatory functions of calpain 1 and 2 during neural stem cell self-renewal and differentiation. | 2012 |
|
| Neuroprotective effects of MAPK/ERK1/2 and calpain inhibitors on lactacystin-induced cell damage in primary cortical neurons. | 2011-12 |
|
| P73 regulates cisplatin-induced apoptosis in ovarian cancer cells via a calcium/calpain-dependent mechanism. | 2011-10-13 |
|
| Dehydroeburicoic acid induces calcium- and calpain-dependent necrosis in human U87MG glioblastomas. | 2009-11 |
|
| Calpain as a potential therapeutic target in Parkinson's disease. | 2008-06 |
|
| Mechanism of arsenic-induced neurotoxicity may be explained through cleavage of p35 to p25 by calpain. | 2008-04 |
|
| Cadmium induces Ca2+-dependent necrotic cell death through calpain-triggered mitochondrial depolarization and reactive oxygen species-mediated inhibition of nuclear factor-kappaB activity. | 2007-03 |
|
| Degraded collagen induces calpain-mediated apoptosis and destruction of the X-chromosome-linked inhibitor of apoptosis (xIAP) in human vascular smooth muscle cells. | 2006-02-15 |
|
| Arsenic trioxide-induced death of neuroblastoma cells involves activation of Bax and does not require p53. | 2004-05-01 |
|
| Inhibition of proteolysis by a cyclooxygenase inhibitor, indomethacin. | 2000-11 |
|
| Role of calpain in spinal cord injury: effects of calpain and free radical inhibitors. | 1998-05-30 |
|
| Mechanism of growth inhibition by calpain inhibitor in MCF-7 cells. | 1997-05-01 |
|
| Role of intracellular proteases in differentiation of L6 myoblast cells. | 1994-03 |
|
| Synthesis of a new cell penetrating calpain inhibitor (calpeptin). | 1988-06-30 |
Patents
Sample Use Guides
Mice: 0.04 mg three times a week for 4 weeks
Route of Administration:
Intraperitoneal
Calpeptin suppressed the proliferation of SW1990 cells at high doses (>20 uM), whereas calpeptin did not suppress proliferation at low doses (1 or 10 uM; P<0.05). The IC50 value was 74.2 uM. Calpeptin similarly suppressed the proliferation of SUIT-2 cells and inhibited the migration (P < 0.05) and invasion (P < 0.05) of pancreatic cancer cells.
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
18X9FR245W
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| Record Status |
Validated (UNII)
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| Record Version |
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