LEUPEPTIN

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 Search

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

Molecular Formula	C20H38N6O4
Molecular Weight	426.5535
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4243683 | https://www.ncbi.nlm.nih.gov/pubmed/15804428 | https://www.ncbi.nlm.nih.gov/pubmed/14704627 | https://www.ncbi.nlm.nih.gov/pubmed/5044133

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Protein methylesterase (rat) 3 Target ID: Protein methylesterase (rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3814152	Inhibitor 8297	35.0 nM [Ki]
Thrombokinase (Bos taurus) 3 Target ID: Thrombokinase (Bos taurus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/4243683	Inhibitor 8297
Trypsin 7 Target ID: CHEMBL2366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4243683 \| https://www.ncbi.nlm.nih.gov/pubmed/1911768	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Skin cancer 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5044133	Primary	Preclinical	Unknown Approved Use Unknown
Gingivitis 44 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11243579	Primary	Preclinical	Unknown Approved Use Unknown
Myocardial stunning 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14704627 https://www.ncbi.nlm.nih.gov/pubmed/7690085	Preventing	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of the growth of human coronavirus 229E by leupeptin.	1985 Feb	3968542
Purification and biochemical characterization of recombinant simian immunodeficiency virus protease and comparison to human immunodeficiency virus type 1 protease.	1991 Aug 27	1883829
Efficacy of serine protease inhibitors against Cryptosporidium parvum infection in a bovine fallopian tube epithelial cell culture system.	1996 Aug	8691375
Activation and enzymatic characterization of recombinant human kallikrein 8.	2006 Jun	16800733
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	19464575
Urban particulate matter activates Akt in human lung cells.	2012 Jan	21818627

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:42:21 GMT 2023` Edited by `admin` on `Fri Dec 15 15:42:21 GMT 2023`
Record UNII	J97339NR3V
Record Status	`Validated (UNII)`
Record Version

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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

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

49690