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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H38N6O4
Molecular Weight 426.5535
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEUPEPTIN

SMILES

CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C=O

InChI

InChIKey=GDBQQVLCIARPGH-ULQDDVLXSA-N
InChI=1S/C20H38N6O4/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)/t15-,16-,17-/m0/s1

HIDE SMILES / InChI
Leupeptin is produced by various species of Actinomycetes. It strongly inhibits proteolysis by plasmin, trypsin and papin. Leupeptin is well absorbed through oral route. Leupeptin has been known to cause various neuropathological changes in vivo resembling those of aging or neurodegenerative processes in the human brain, including the accumulation of neuronal processes and neuronal cytoskeletal abnormalities leading to neurofibrillary tangle (NFT)-like formations. In in vitro experiments, leupeptin protects the heart from myocardial stunning. Leupeptin was found to inhibit tumorigenesis in mouse skin induced by a single, noncarcinogenic dose of 7,12- dimethylbenz(a)anthracene followed by repeated application of croton oil. Tumors that had already been induced were scarcely affected by leupeptin.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Protein methylesterase (rat)
35.0 nM [Ki]
Target ID: Thrombokinase (Bos taurus)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Drug-induced lysosomal changes and nephrotoxicity in rats.
1978 Nov
Inhibition of the growth of human coronavirus 229E by leupeptin.
1985 Feb
Purification and biochemical characterization of recombinant simian immunodeficiency virus protease and comparison to human immunodeficiency virus type 1 protease.
1991 Aug 27
Peptide aldehydes as inhibitors of HIV protease.
1993 Mar 22
Antiviral effect of oryzacystatin, a proteinase inhibitor in rice, against herpes simplex virus type 1 in vitro and in vivo.
1995 Apr
Efficacy of serine protease inhibitors against Cryptosporidium parvum infection in a bovine fallopian tube epithelial cell culture system.
1996 Aug
Cryptosporidium parvum metalloaminopeptidase inhibitors prevent in vitro excystation.
1996 Dec
Characterization of cytochrome P4502E1 turnover in transfected HepG2 cells expressing human CYP2E1.
1997 May 1
Inhibition of proteolysis by a cyclooxygenase inhibitor, indomethacin.
2000 Nov
Transforming growth factor-beta1 inhibits all-trans retinoic acid-induced apoptosis.
2006 May
2,2',4,4',5,5'-hexachlorobiphenyl (PCB 153) induces degradation of adherens junction proteins and inhibits beta-catenin-dependent transcription in liver epithelial cells.
2009 Jun 16
Molecular modeling: a search for a calpain inhibitor as a new treatment for cataractogenesis.
2011 Nov 10
Urban particulate matter activates Akt in human lung cells.
2012 Jan
Patents

Sample Use Guides

Rat: 0.2 ml (1 mg/ml) was administrated five times at 2-h intervals per day.
Route of Administration: Oral
In Vitro Use Guide
The activity of the skin TAME (p-toluene-sulfonyl-L-arginine methyl ester) esterase had increased almost 2.5 times at 24 hr after 0.3% croton oil treatment. The TAME esterase activity was significantly inhibited by addition of leupeptin, 0.1 mg/ml, and it was progressively inhibited by higher concentrations of leupeptin. The activity was less than 10% of the control in the presence of leupeptin, 2.5 mg/ml.
Name Type Language
LEUPEPTIN
Common Name English
L-LEUCINAMIDE, N-ACETYL-L-LEUCYL-N-((1S)-4-((AMINOIMINOMETHYL)AMINO)-1-FORMYLBUTYL)-
Systematic Name English
ACETYL-LEUCYL-LEUCYL-ARGININAL
Systematic Name English
LEUPEPTINS [MI]
Common Name English
L-LEUCINAMIDE, N-ACETYL-L-LEUCYL-N-(4-((AMINOIMINOMETHYL)AMINO)-1-FORMYLBUTYL)-, (S)-
Systematic Name English
ACETYL-L-LEUCYL-L-LEUCYL-L-ARGININAL
Systematic Name English
LEUPEPTINS
MI  
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 49690
Created by admin on Fri Dec 15 15:42:21 GMT 2023 , Edited by admin on Fri Dec 15 15:42:21 GMT 2023
Code System Code Type Description
WIKIPEDIA
LEUPEPTIN
Created by admin on Fri Dec 15 15:42:21 GMT 2023 , Edited by admin on Fri Dec 15 15:42:21 GMT 2023
PRIMARY
FDA UNII
J97339NR3V
Created by admin on Fri Dec 15 15:42:21 GMT 2023 , Edited by admin on Fri Dec 15 15:42:21 GMT 2023
PRIMARY
PUBCHEM
72429
Created by admin on Fri Dec 15 15:42:21 GMT 2023 , Edited by admin on Fri Dec 15 15:42:21 GMT 2023
PRIMARY
MERCK INDEX
m6778
Created by admin on Fri Dec 15 15:42:21 GMT 2023 , Edited by admin on Fri Dec 15 15:42:21 GMT 2023
PRIMARY Merck Index
MESH
C032854
Created by admin on Fri Dec 15 15:42:21 GMT 2023 , Edited by admin on Fri Dec 15 15:42:21 GMT 2023
PRIMARY
CAS
55123-66-5
Created by admin on Fri Dec 15 15:42:21 GMT 2023 , Edited by admin on Fri Dec 15 15:42:21 GMT 2023
PRIMARY