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
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
| Molecular Formula | C16H26N2O6S2 |
| Molecular Weight | 406.517 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pre-clinical and Clinical Safety Studies of CMX-2043: a cytoprotective lipoic acid analogue for ischaemia-reperfusion injury. | 2014 Nov |
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| CMX-2043 Efficacy in a Rat Model of Cardiac Ischemia-Reperfusion Injury. | 2016 Nov |
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| CMX-2043 Mechanisms of Action In Vitro. | 2016 Sep |
Patents
| Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 08:37:53 GMT 2023
by
admin
on
Sat Dec 16 08:37:53 GMT 2023
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| Record UNII |
83V80O4XY1
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| Record Status |
Validated (UNII)
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ACTIVE MOIETY |
The CMX-2043 in vitro ADME profile is shown in table 2.
CMX-2043 was approximately 59.8% protein bound at a con-
centration of 4.065 lg/mL (10 lM). Other solution properties included solubility of > 100 mg/mL (PBS, pH 7.4) and ClogP of
0.27. CMX-2043 at a concentration of 0.4065 lg/mL (1 lM) was stable in human liver microsomes for 60 min. at 37C.
CMX-2043 was stable in human plasma for at least 60 min. at 37C at a concentration of 2.032 lg/mL (5 lM). At a concentration of 4.065 lg/mL (10 lM), CMX-2043 had an insignificant or no inhibitory effect on the human cytochrome P450
enzyme subtypes CYP1A2, CYP2C9, CYP2E1, CYP2B6,
CYP2C19, CYP3A4, CYP2C8, CYP2D6, CYP3A5.
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ACTIVE MOIETY |
Originator: Ischemix; Class: Ischaemic heart disorder therapy, Small molecule; Mechanism of Action: Proto oncogene protein c akt modulator; Orphan Drug Status: No; On Fast track: No
New Molecular Entity: Yes; Available For Licensing: Yes; Highest Development Phase: Phase II for Reperfusion injury; Most Recent Events: 03 May 2016 The phase IIa CARIN trial in Reperfusion injury (Prevention) did not meet the pre-specified endpoints, 09 Dec 2015 Ischemix receives patent allowance for CMX-2043 in New Zealand, 30 Sep 2015 Ischemix completes enrolment in the phase IIa CARIN trial for Reperfusion injury (Prevention) in USA and Canada (NCT02103959)
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ACTIVE MOIETY |
Official Title: A Prospective, Comparative, Randomized, Multi-Center, Double-Blinded, Placebo-Controlled, Phase 2a Study of the Safety and Efficacy of CMX-2043 for Periprocedural Injury Protection in Subjects Undergoing Coronary Angiography at Risk of Radio-contrast Induced Nephropathy (CARIN)
Purpose: The objective of this study is to evaluate CMX-2043 for prevention of renal and cardiac injury associated with coronary angiography in patients with acute coronary syndrome (ACS), but excluding ST-elevation myocardial infarction (STEMI) patients. This study will specifically examine the ability of CMX-2043 to prevent acute renal injury following coronary angiography. The study will also examine the ability of CMX 2043 for prevention of periprocedural cardiac injury. Information will be obtained relating to the ability of CMX 2043 for prevention of major adverse cardiac and renal events following the procedure. Additional information will be obtained in this study to evaluate safety of the drug. Dose and regimen information will also be obtained for future clinical studies of CMX-2043.
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