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 |
|---|---|---|
| Synthesis of a new cell penetrating calpain inhibitor (calpeptin). | 1988 Jun 30 |
|
| Role of intracellular proteases in differentiation of L6 myoblast cells. | 1994 Mar |
|
| Mechanism of growth inhibition by calpain inhibitor in MCF-7 cells. | 1997 May-Jun |
|
| Role of calpain in spinal cord injury: effects of calpain and free radical inhibitors. | 1998 May 30 |
|
| Inhibition of proteolysis by a cyclooxygenase inhibitor, indomethacin. | 2000 Nov |
|
| Arsenic trioxide-induced death of neuroblastoma cells involves activation of Bax and does not require p53. | 2004 May 1 |
|
| Degraded collagen induces calpain-mediated apoptosis and destruction of the X-chromosome-linked inhibitor of apoptosis (xIAP) in human vascular smooth muscle cells. | 2006 Feb 15 |
|
| Cadmium induces Ca2+-dependent necrotic cell death through calpain-triggered mitochondrial depolarization and reactive oxygen species-mediated inhibition of nuclear factor-kappaB activity. | 2007 Mar |
|
| Mechanism of arsenic-induced neurotoxicity may be explained through cleavage of p35 to p25 by calpain. | 2008 Apr |
|
| Calpain as a potential therapeutic target in Parkinson's disease. | 2008 Jun |
|
| Dehydroeburicoic acid induces calcium- and calpain-dependent necrosis in human U87MG glioblastomas. | 2009 Nov |
|
| Neuroprotective effects of MAPK/ERK1/2 and calpain inhibitors on lactacystin-induced cell damage in primary cortical neurons. | 2011 Dec |
|
| P73 regulates cisplatin-induced apoptosis in ovarian cancer cells via a calcium/calpain-dependent mechanism. | 2011 Oct 13 |
|
| Distinct regulatory functions of calpain 1 and 2 during neural stem cell self-renewal and differentiation. | 2012 |
|
| Anti-breast cancer effects of histone deacetylase inhibitors and calpain inhibitor. | 2012 Jul |
|
| Amelioration of cisplatin-induced experimental peripheral neuropathy by a small molecule targeting p75 NTR. | 2014 Dec |
|
| Calpain inhibitor calpeptin suppresses pancreatic cancer by disrupting cancer-stromal interactions in a mouse xenograft model. | 2016 Oct |
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
by
admin
on
Edited
Fri Dec 15 18:07:36 GMT 2023
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admin
on
Fri Dec 15 18:07:36 GMT 2023
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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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