LEUPEPTIN HEMISULFATE MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C20H38N6O4.2H2O.H2O4S
Molecular Weight	987.216
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LEUPEPTIN HEMISULFATE MONOHYDRATE

Structure Search

SMILES

O.O.OS(O)(=O)=O.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.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=FWGRMOYQEJXKOZ-XZZFGKIVSA-N

InChI=1S/2C20H38N6O4.H2O4S.2H2O/c2*1-12(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;1-5(2,3)4;;/h2*11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);(H2,1,2,3,4);2*1H2/t2*15-,16-,17-;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Purification and biochemical characterization of recombinant simian immunodeficiency virus protease and comparison to human immunodeficiency virus type 1 protease.	1991 Aug 27	1883829
Peptide aldehydes as inhibitors of HIV protease.	1993 Mar 22	8458418
Antiviral effect of oryzacystatin, a proteinase inhibitor in rice, against herpes simplex virus type 1 in vitro and in vivo.	1995 Apr	7785982
Efficacy of serine protease inhibitors against Cryptosporidium parvum infection in a bovine fallopian tube epithelial cell culture system.	1996 Aug	8691375
Cryptosporidium parvum metalloaminopeptidase inhibitors prevent in vitro excystation.	1996 Dec	9124840
Characterization of cytochrome P4502E1 turnover in transfected HepG2 cells expressing human CYP2E1.	1997 May 1	9143349
Inhibition of proteolysis by a cyclooxygenase inhibitor, indomethacin.	2000 Nov	11071371
Proteasomal degradation of caspase-6 in 17beta-estradiol-treated neurons.	2004 May	15086513
Activation and enzymatic characterization of recombinant human kallikrein 8.	2006 Jun	16800733
Transforming growth factor-beta1 inhibits all-trans retinoic acid-induced apoptosis.	2006 May	16242776
Endothelial gap junctions are down-regulated by arsenic trioxide.	2007 Aug 13	17559834
Regulation of adipocyte lipolysis by degradation of the perilipin protein: nelfinavir enhances lysosome-mediated perilipin proteolysis.	2007 Jul 27	17488708
Defective hepatocyte aquaporin-8 expression and reduced canalicular membrane water permeability in estrogen-induced cholestasis.	2007 Mar	17110522
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
Molecular modeling: a search for a calpain inhibitor as a new treatment for cataractogenesis.	2011 Nov 10	21955158

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 20:04:30 GMT 2023` Edited by `admin` on `Fri Dec 15 20:04:30 GMT 2023`
Record UNII	P4TZ8HY7S7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEUPEPTIN HEMISULFATE MONOHYDRATE

Common Name

English

L-LEUCINAMIDE, N-ACETYL-L-LEUCYL-N-((1S)-4-((AMINOIMINOMETHYL)AMINO)-1-FORMYLBUTYL)-, SULFATE, HYDRATE (2:1:2)

Common Name

English

Code System Code Type Description

PUBCHEM

71587926

Created by admin on Fri Dec 15 20:04:30 GMT 2023 , Edited by admin on Fri Dec 15 20:04:30 GMT 2023

PRIMARY

FDA UNII

P4TZ8HY7S7

Created by admin on Fri Dec 15 20:04:30 GMT 2023 , Edited by admin on Fri Dec 15 20:04:30 GMT 2023

PRIMARY

EPA CompTox

DTXSID70148463

Created by admin on Fri Dec 15 20:04:30 GMT 2023 , Edited by admin on Fri Dec 15 20:04:30 GMT 2023

PRIMARY

CAS

1082207-96-2

Created by admin on Fri Dec 15 20:04:30 GMT 2023 , Edited by admin on Fri Dec 15 20:04:30 GMT 2023

PRIMARY

Related Record Type Details


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LEUPEPTIN HEMISULFATE ANHYDROUS

ANHYDROUS->SOLVATE

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					J97339NR3V

LEUPEPTIN

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: 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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

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