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Merck
CN

C5732

CA-074

synthetic (organic), ≥98% (HPLC), cathepsin B inhibitor, powder

Synonym(s):

(L-3-trans-(Propylcarbamyl)oxirane-2-carbonyl)-L-isoleucyl-L-proline

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About This Item

Empirical Formula (Hill Notation):
C18H29N3O6
CAS Number:
134448-10-5
Molecular Weight:
383.44
UNSPSC Code:
12352200
PubChem Substance ID:
24892580
NACRES:
NA.77
MDL number:
MFCD00797531

Key Documents

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Product Name

CA-074, ≥98% (HPLC)

SMILES string

CCCNC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H]([C@H](C)CC)C(=O)N2CCC[C@H]2C(O)=O

InChI key

ZEZGJKSEBRELAS-NSIINPIOSA-N

InChI

1S/C18H29N3O6/c1-4-8-19-15(22)13-14(27-13)16(23)20-12(10(3)5-2)17(24)21-9-6-7-11(21)18(25)26/h10-14H,4-9H2,1-3H3,(H,19,22)(H,20,23)(H,25,26)/t10?,11-,12-,13-,14-/m0/s1

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

solubility

methanol: 1 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

Related Categories

Application

CA-074 has been used as a cathepsin B inhibitor:
  • to study its effect on pseudotyped viruses bearing S proteins harboring R642M and N714K using HeLa cells
  • to determine the role of autophagy in glucose deprivation (GD)-induced damage
  • to study its effects on neuronal function upon exposure to His-cathepsin B (CATB)

Biochem/physiol Actions

CA-074 is a potent and a selective inhibitor of cathepsin B. It is useful to study the biological function of cathepsin B in vivo. Studies show that CA-074 can also inhibit cathepsin L under reducing conditions.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000502243
0000502243
0000467481
0000467481
SLCN6839

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Igor Stern et al.
The Biochemical journal, 381(Pt 2), 511-517 (2004-04-16)
The crystal structure of the inhibitor NS-134 in complex with bovine cathepsin B reveals that functional groups attached to both sides of the epoxysuccinyl reactive group bind to the part of active-site cleft as predicted. The -Leu-Pro-OH side binds to
The cathepsin B-selective inhibitors CA-074 and CA-074Me inactivate cathepsin L under reducing conditions
Steverding D
Open enzyme inhibition Journal, 4, 11-16 (2011)
M Murata et al.
FEBS letters, 280(2), 307-310 (1991-03-25)
A series of new epoxysuccinyl peptides were designed and synthesized to develop a specific inhibitor of cathepsin B. Of these compounds, N-(L-3-trans-ethoxycarbonyloxirane-2-carbonyl)-L-isoleucyl-L-proli ne (compound CA-030) and N-(L-3-trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-prol ine (compound CA-074) were the most potent and specific inhibitors of cathepsin B
Giuseppe Nicastro et al.
Proceedings of the National Academy of Sciences of the United States of America, 102(30), 10493-10498 (2005-07-16)
The Josephin domain plays an important role in the cellular functions of ataxin-3, the protein responsible for the neurodegenerative Machado-Joseph disease. We have determined the solution structure of Josephin and shown that it belongs to the family of papain-like cysteine
Masashi Asai et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 25(10), 3720-3730 (2011-07-13)
γ-Secretase catalyzes the cleavage of the intramembrane region of the Alzheimer amyloid precursor protein (APP), generating p3, amyloid-β peptide (Aβ), and the APP intracellular domain (AICD). Although a γ-secretase inhibitor has been shown to cause an accumulation of the APP
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