E-64

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H27N5O5
Molecular Weight	357.4054
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(=O)[C@H]1O[C@@H]1C(O)=O)C(=O)NCCCCNC(N)=N

InChI

InChIKey=LTLYEAJONXGNFG-DCAQKATOSA-N

InChI=1S/C15H27N5O5/c1-8(2)7-9(20-13(22)10-11(25-10)14(23)24)12(21)18-5-3-4-6-19-15(16)17/h8-11H,3-7H2,1-2H3,(H,18,21)(H,20,22)(H,23,24)(H4,16,17,19)/t9-,10-,11-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H27N5O5
Molecular Weight	357.4054
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/1440613

E-64 is an inhibitor of calpain and other cysteine proteases such as cathepsin B, cathepsin L, cathepsin H. The low toxic effects of the inhibitor, in addition to its effective mechanism of action, makes E-64 a potential template for drugs to treat diseases where high levels of a cysteine proteases are the primary cause. It was discovered, that this drug slowed the rate of formation of cataract in cultured rat lenses, but this study was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cathepsin B 9 Target ID: CHEMBL4072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7044372	Inhibitor 8504
Cathepsin L 4 Target ID: CHEMBL3837 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7044372	Inhibitor 8504
Cathepsin H 2 Target ID: CHEMBL2225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7044372	Inhibitor 8504
Calpain1/2 1 Target ID: CHEMBL3038466 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1848210	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cataract 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1848210	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Crystal structure of a papain-E-64 complex.	1989-02-07	2713367
L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L.	1982-01-01	7044372

Sample Use Guides

In Vivo Use Guide

in rats teratogenic effects: Wistar rats were injected with 10-30 mg/kg of E-64 intra-peritoneally on days 9 and 10 of gestation

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:06:37 GMT 2025` Edited by `admin` on `Mon Mar 31 19:06:37 GMT 2025`
Record UNII	R76F7856MV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

E-64

Common Name

English

PROTEINASE INHIBITOR E-64

Preferred Name

English

2-OXIRANECARBOXYLIC ACID, 3-((((1S)-1-(((4-((AMINOIMINOMETHYL)AMINO)BUTYL)AMINO)CARBONYL)-3-METHYLBUTYL)AMINO)CARBONYL)-, (2S,3S)-

Systematic Name

English

Code System Code Type Description

PUBCHEM

123985