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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H26N2O6S2
Molecular Weight 406.517
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CMX-2043

SMILES

C[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)CCCC[C@@H]1CCSS1)C(O)=O

InChI

InChIKey=MQXRTCVZPIHBLD-TUAOUCFPSA-N
InChI=1S/C16H26N2O6S2/c1-10(16(23)24)17-15(22)12(6-7-14(20)21)18-13(19)5-3-2-4-11-8-9-25-26-11/h10-12H,2-9H2,1H3,(H,17,22)(H,18,19)(H,20,21)(H,23,24)/t10-,11+,12-/m0/s1

HIDE SMILES / InChI
CMX-2043 is a is an α-lipoic acid analog developed by Ischemix LLC for reduction of cellular injury and organ damage due to ischemia-reperfusion injury (IRI). CMX-2043 was more effective than lipoic acid in antioxidant effect, activation of insulin receptor kinase, soluble tyrosine kinase, and Akt phosphorylation, and activated insulin-like growth factor 1 as effectively as lipoic acid. In a rat model of cardiac ischemia-reperfusion injury, treatment with CMX-2043 reduced myocardial IRI as measured by the myocardial infarction/area at risk ratio, and reduced the incidence of arrhythmia. In a 360-patient Phase 2 trial, CMX-2043 demonstrated safety but did not meet pre-specified endpoints regarding prevention of contrast-induced acute kidney injury or cardiac injury in cardiac catheterization lab subjects, and no further development of the drug was reported.

Approval Year

PubMed

PubMed

TitleDatePubMed
Pre-clinical and Clinical Safety Studies of CMX-2043: a cytoprotective lipoic acid analogue for ischaemia-reperfusion injury.
2014 Nov
CMX-2043 Efficacy in a Rat Model of Cardiac Ischemia-Reperfusion Injury.
2016 Nov
Patents
Name Type Language
CMX-2043
Common Name English
LIP-EA
Common Name English
.ALPHA.-N-((R )-1,2-DITHIOLANE-3-PENTANOYL)-L-GLUTAMYL-L-ALANINE
Common Name English
(R)-LIP-L-GLU-L-ALA-OH
Common Name English
(4S)-4-(5-((3R)-DITHIOLAN-3-YL)PENTANOYLAMINO)-5-(((1S)-2-HYDROXY-1-METHYL-2-OXO-ETHYL)AMINO)-5-OXO-PENTANOIC ACID
Systematic Name English
R-LIPOIC ACID-L-GLUTAMATE-L-ALANINE
Common Name English
L-ALANINE, N-(5-(3R)-1,2-DITHIOLAN-3-YL-1-OXOPENTYL)-L-.ALPHA.-GLUTAMYL-
Systematic Name English
R-LIP-EA-OH
Common Name English
Code System Code Type Description
CAS
910627-26-8
Created by admin on Sat Dec 16 08:37:53 GMT 2023 , Edited by admin on Sat Dec 16 08:37:53 GMT 2023
PRIMARY
PUBCHEM
49802864
Created by admin on Sat Dec 16 08:37:53 GMT 2023 , Edited by admin on Sat Dec 16 08:37:53 GMT 2023
PRIMARY
DRUG BANK
DB12795
Created by admin on Sat Dec 16 08:37:53 GMT 2023 , Edited by admin on Sat Dec 16 08:37:53 GMT 2023
PRIMARY
FDA UNII
83V80O4XY1
Created by admin on Sat Dec 16 08:37:53 GMT 2023 , Edited by admin on Sat Dec 16 08:37:53 GMT 2023
PRIMARY