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Safety Information

C5732

Sigma-Aldrich

CA-074

≥98% (HPLC)

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
MDL number:
MFCD00797531
UNSPSC Code:
12352200
PubChem Substance ID:
24892580
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

methanol: 1 mg/mL, clear, colorless

storage temp.

−20°C

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

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

InChI key

ZEZGJKSEBRELAS-NSIINPIOSA-N

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLCN6839
SLCL7511
SLCL0989
SLCB8931
SLBX5549

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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
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)
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
Eduardo Villalobo et al.
Eukaryotic cell, 2(6), 1234-1245 (2003-12-11)
The process of excystment of Sterkiella histriomuscorum (Ciliophora, Oxytrichidae) leads in a few hours, through a massive influx of water and the resorption of the cyst wall, from an undifferentiated resting cyst to a highly differentiated and dividing vegetative cell.
Arjen R de Boer et al.
Analytical chemistry, 77(24), 7894-7900 (2005-12-15)
The potential of high-temperature liquid chromatography (HTLC) was investigated in an on-line combination with a screening system for bioactive compounds against the enzyme cathepsin B. Samples were separated by HTLC and subsequently analyzed by an on-line continuous-flow enzymatic assay. Detection
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