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Loxistatin

Loxistatin structure

CAS No:
88321-09-9
Formula:
C17H30N2O5
Chemical Name:
Loxistatin
Synonyms:
2-Oxiranecarboxylic acid,3-[[[(1S)-3-methyl-1-[[(3-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-,ethyl ester,(2S,3S)-;Oxiranecarboxylic acid,3-[[[3-methyl-1-[[(3-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-,ethyl ester,[2S-[2α,3β(R*)]]-;Oxiranecarboxylic acid,3-[[[(1S)-3-methyl-1-[[(3-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-,ethyl ester,(2S,3S)-;EP 453;EST;E 64d;Loxistatin;E 64c ethyl ester;Aloxistatin;EST (pharmaceutical);NSC 694281;Pepstatin E64d;E64d/pepstatin;207396-71-2
Categories:
Biochemical Engineering > Inhibitors

Description

Aloxistatin (E64d) is a cell-permeable and irreversible broad-spectrum cysteine protease inhibitor.

Aloxistatin is an L-leucine derivative that is the amide obtained by formal condensation of the carboxy group of (2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid with the amino group of N-(3-methylbutyl)-L-leucinamide. It has a role as a cathepsin B inhibitor and an anticoronaviral agent. It is a L-leucine derivative, a monocarboxylic acid amide, an epoxide and an ethyl ester.|Aloxistatin is an inhibitor of cysteine protease with blood platelet aggregation inhibiting activity. Aloxistatin is an irreversible, membrane-permeable inhibitor of lysosomal and cytosolic cysteine proteases with the ability to inhibit calpain activity in intact platelets.

Loxistatin Basic Attributes

Molecular Weight：

342.43

Exact Mass：

342.43

UNII：

L5W337AOUR

NCI Thesaurus Code：

C76907

HScode：

29242990

Characteristics

PSA：

XLogP3：

2.3

Density：

1.2±0.1 g/cm3

Melting Point：

126.2°C

Boiling Point：

538°C at 760 mmHg

Flash Point：

238.4±31.5 °C

Refractive Index：

1.530

Water Solubility：

Soluble in DMSO, DMF or ethanol

Storage Conditions：

−20°C

Toxicity：

cyt-ham:lng 200 mg/L IYKEDH 17,815,86

Safety Information

Transport codes：

3077

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36-24/25

RTECS Number：

RR0404300

Marks：

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)|Exogenous and endogenous compounds which inhibit CYSTEINE ENDOPEPTIDASES. (See all compounds classified as Cysteine Proteinase Inhibitors.)

MeSH Entry Terms：

(2S,3S)-trans-epoxysuccinyl-L-leucylamido-3-methylbutane ethyl ester

Loxistatin Use and Manufacturing

Methods of Manufacturing

To a solution of (2S, 3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid (5) (25 g, 0.16 mol) and (S)-1-(isopentylamino)-2-amino-4-methyl-1-oxopentan hydrochloride (3c) (38 g, 0.16 mol) in CHTo a solution of (2S, 3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid (5) (4.6 g, 27 mmol) and (S)-1-(isopentylamino)-4-methyl-1-oxopentan-2-aminium 4-methylbenzenesulfonate (3b) (11 g, 29 mmol) in CH

Uses

E-64d is an inhibitor of cathepsins B and L as well as a potential inhibitor of calpain. E-64d has been shown to inhibit lysosomal proteases. E-64d has been used in combination with Prepstatin A to interfere with autolysosomal digestion. E-64d displays neurovascular and neuronal protective effects after focal cerebral ischemia in rats.

Computed Properties

Molecular Weight:342.4
XLogP3:2.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:11
Exact Mass:342.21547206
Monoisotopic Mass:342.21547206
Topological Polar Surface Area:97
Heavy Atom Count:24
Complexity:450
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Aloxistatin

CAS No.: 88321-09-9

Content: 99.00%

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