117591-20-5 Usage
Uses
Used in Pharmaceutical Applications:
CALPEPTIN is used as an inhibitor for the activities of cathepsin L and calpain-1, blocking the expression of aspartyl protease cathepsin D, amyloid precursor protein, and calparin. It acts as an inhibitor of the Ca2+-dependent protease, calpain, and prevents collagenand thrombin-induced platelet aggregation, likely by blocking calpain-induced phospholipase C and thromboxane synthase activation.
Used in Neuroprotection:
CALPEPTIN is used as a neuroprotective agent for the treatment of experimental autoimmune encephalomyelitis (EAE) and multiple sclerosis (MS) due to its ability to decrease microgliosis, astrogliosis, axonal damage, and neuron and oligodendrocyte death in EAE spinal cord.
Used in Enzyme Inhibition:
CALPEPTIN is used as a potent cathepsin L inhibitor and has been shown to preferentially inhibit a subset of protein-tyrosine phosphatases, making it a valuable tool in the study and regulation of these enzymes.
Biological Activity
Potent, cell-permeable inhibitor of the Ca 2+ -dependent protease, calpain. Prevents collagen- and thrombin-induced platelet aggregation, probably by blocking calpain induced phospholipase C and thromboxane synthase activation. Potent cathepsin L inhibitor. Recently shown to preferentially inhibit a subset of protein-tyrosine phosphatases.
Biochem/physiol Actions
Calpeptin is a rho kinase activator and an inhibitor of calpains, a family of calcium-dependent cysteine proteases involved in apoptosis, long-term potentiation in neurons, and cell cycle progression.
in vitro
calpeptin reduced production of tgf-b1, il-6, angiopoietin-1 and collagen synthesis from lung fibroblasts. calpeptin also reduced both angiopoietin-1-dependent migration and il-6-dependent proliferation of the cells, which could be the underlying mechanism of the preventive effect of calpeptin on pulmonary fibrosis [1].
in vivo
the preventive effect of calpeptin has been examined on bleomycin-induced pulmonary fibrosis in mice. histological examinations and quantitative measurements of related proteins in bleomycin-treated mouse lung tissues with or without calpeptin were performed. calpeptin histologically ameliorated bleomycininduced pulmonary fibrosis in mice. results showed that calpeptin decreased the expression of il-6, tgf-b1, angiopoietin-1 and collagen type ia1 mrna in mouse lung tissues [1].
IC 50
5 nm for human calpain 1
references
[1] tabata c,tabata r,nakano t. the calpain inhibitor calpeptin prevents bleomycin-induced pulmonary fibrosis in mice. clin exp immunol.2010 dec;162(3):560-7.
Check Digit Verification of cas no
The CAS Registry Mumber 117591-20-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,7,5,9 and 1 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 117591-20:
(8*1)+(7*1)+(6*7)+(5*5)+(4*9)+(3*1)+(2*2)+(1*0)=125
125 % 10 = 5
So 117591-20-5 is a valid CAS Registry Number.
InChI:InChI=1/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
117591-20-5Relevant academic research and scientific papers
Cycloalkylcarbonylamino Acid Derivative and Process For Producing The Same
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Page/Page column 68, (2009/05/28)
Cycloalkylcarbonylamino acid derivatives, which are raw material intermediates of a novel cycloalkane carboxamide derivative that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkylcarbonylamino acid derivative r
Cycloalkylcarbonylamino Acid Ester Derivative and Process for Producing The Same
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Page/Page column 68, (2009/06/27)
Cycloalkylcarbonylamino acid ester derivatives, which are raw material intermediates for a novel cycloalkane carboxamide derivative having an action that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkylcarbony
OXAZOLONE DERIVATIVE
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Page/Page column 92-93, (2008/12/07)
Novel raw material compounds are provided that are useful for producing novel cycloalkane carboxamide derivatives having cathepsin K inhibitory action. An oxazolone derivative represented by formula (I): [wherein, R1 represents a substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted phenyl group, substituted or unsubstituted naphthyl group or substituted or unsubstituted heterocyclic group, and ring A represents a saturated cyclic alkylidene group having 6 to 7 carbon atoms].
CYCLOALKANECARBOXAMIDE DERIVATIVE AND METHOD FOR PRODUCING SAME
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Page/Page column 96, (2008/12/08)
Novel cycloalkane carboxamide derivatives having an action that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkane carboxamide derivative represented by the following general formula (I), or a pharmaceutically acceptable salt thereof: (wherein R1 and R2 represent (substituted) alkyl groups, (substituted) alkenyl groups, (substituted) alkynyl groups, (substituted) aromatic hydrocarbon groups or (substituted) heterocyclic groups, ring A represents an alkylidene group having 5 to 7 carbon atoms, and ring B represents a formyl group or a hydroxymethyl group).
Ketoheterocycle-based inhibitors of cathepsin K: A novel entry into the synthesis of peptidic ketoheterocycles
Tavares, Francis X.,Deaton, David N.,Miller, Aaron B.,Miller, Larry R.,Wright, Lois L.
, p. 3891 - 3895 (2007/10/03)
Ketoheterocyclic inhibitors of cathepsin K have been disclosed. SAR of potency enhancing P2-P3 groups coupled with ketoheterocyclic warheads to provide cathepsin K inhibitors have been described. In addition, a novel route to access
PROTEINASE INHIBITOR
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, (2008/06/13)
A novel N-substituted peptidyl compound represented by the general formula (1): STR1 where R 1 is a straight-chained or branched acyl group having 2-10 carbon atoms, a branched, cyclic or partly branched cyclic alkyloxycarbonyl group having 4-15 carbon at
