ALRESTATIN SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H8NO4.Na
Molecular Weight	277.2074
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[O-]C(=O)CN1C(=O)C2=CC=CC3=CC=CC(C1=O)=C23

InChI

InChIKey=FKZUETPACPDEAD-UHFFFAOYSA-M

InChI=1S/C14H9NO4.Na/c16-11(17)7-15-13(18)9-5-1-3-8-4-2-6-10(12(8)9)14(15)19;/h1-6H,7H2,(H,16,17);/q;+1/p-1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8003482 | https://www.ncbi.nlm.nih.gov/pubmed/8329799

Alrestatin, an inhibitor of aldose reductase, was studied in clinical trials for the treatment of diabetes. But this study was discontinued, because of the high hepatotoxicity events.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aldose reductase 44 Target ID: P15121 Gene ID: 231.0 Gene Symbol: AKR1B1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8003482	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/122298	Primary		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Proteomic analysis of oxidative stress-resistant cells: a specific role for aldose reductase overexpression in cytoprotection.	2004 Feb	14676331
Upregulation of aldose reductase by homocysteine in type II alveolar epithelial cells.	2005 Dec 2	16225842
Mechanism of high glucose induced angiotensin II production in rat vascular smooth muscle cells.	2007 Aug 31	17626897
Advances in pharmacological strategies for the prevention of cataract development.	2009 May-Jun	19384010
Diabetic cataract-pathogenesis, epidemiology and treatment.	2010	20634936

Sample Use Guides

In Vivo Use Guide

diabetic patients with severe peripheral neuropathy: intravenously (50 mg/kg body weight); orally (1 gm q.i.d.)

Route of Administration: Other

In Vitro Use Guide

Alrestatin (10 uM) attenuated the effect of high glucose (HG) to increase angiotensin (Ang) II accumulation in cells and media and decrease the Ang I level in media. The partial inhibitory effect of alrestatin could be attributable to posttranscriptional modification of aldose reductase such as S-thiolation, which makes this enzyme less sensitive to inhibitors.

Name

Type

Language

ALRESTATIN SODIUM

Official Name

English

AY-22,284A

Code

English

Sodium 1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetate

Systematic Name

English

Alrestatin sodium [WHO-DD]

Common Name

English

ALRESTATIN SODIUM [MART.]

Common Name

English

AY-22284A

Code

English

ALRESTATIN SODIUM [USAN]

Common Name

English

1H-BENZ(DE)ISOQUINOLINE-2(3H)ACETIC ACID, 1,3-DIOXO-, SODIUM SALT

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C72880