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Merck
CN

L9783

Leupeptin hydrochloride

powder, ≥90% (HPLC)

Synonym(s):

Acetyl-Leu-Leu-Arg-al hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C20H38N6O4 · HCl
CAS Number:
Molecular Weight:
463.01
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Product Name

Leupeptin hydrochloride, microbial, ≥90% (HPLC)

biological source

microbial

Quality Level

assay

≥90% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Cl.CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(CCCNC(N)=N)C=O

InChI

1S/C20H38N6O4.ClH/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22;/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);1H

InChI key

OQQYPQNFLLAILR-UHFFFAOYSA-N

Biochem/physiol Actions

Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM.
Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM. There have been numerous studies using leupeptin to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin. (Loss of cochlear hair cells is believed to be mediated by calpain.)

Analysis Note

Leupeptin gives multiple peaks on HPLC because of the formation of tautomeric isomers in solution. Majority of contaminating peptide is racemized leupeptin.


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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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Pharmacologic inhibition of site 1 protease activity inhibits sterol regulatory element-binding protein processing and reduces lipogenic enzyme gene expression and lipid synthesis in cultured cells and experimental animals.
Hawkins, J.L., et al.
The Journal of Nutrition, 326, 801-808 (2008)
Judi Bryant et al.
Thrombosis research, 122(4), 523-532 (2008-05-23)
ADP plays a key role in platelet aggregation which has led to the development of antiplatelet drugs that target the P2Y12 receptor. The aim of this study was to characterize the effects of two novel P2Y12 receptor antagonists, BX 667
Patrick J Devine et al.
Methods in molecular biology (Clifton, N.J.), 550, 137-157 (2009-06-06)
The female reproductive system is important as the site for development and fertilization of an oocyte, for implantation and development of an embryo, and for growth and delivery of the fetus. It also produces protein and steroid hormones that help



Global Trade Item Number

SKUGTIN
L9783-100MG04061833967003
L9783-25MG04061833967010
L9783-5MG04061833967027