Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H14NOS.Cl |
| Molecular Weight | 267.774 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].CC1=C(C)[N+](CC(=O)C2=CC=CC=C2)=CS1
InChI
InChIKey=MKOMESMZHZNBIZ-UHFFFAOYSA-M
InChI=1S/C13H14NOS.ClH/c1-10-11(2)16-9-14(10)8-13(15)12-6-4-3-5-7-12;/h3-7,9H,8H2,1-2H3;1H/q+1;/p-1
| Molecular Formula | C13H14NOS |
| Molecular Weight | 232.321 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Alagebrium (formerly known as ALT-711) - is one of the better known compounds discovered and developed with the intent of repairing a type of accumulated damage that leads to age-related degeneration. In this case, the damage is the buildup of extracellular protein crosslinks, and amongst them the type known as advanced glycation endproducts. The formation of advanced glycation end-products is associated with arterial stiffness in experimental models and alagebrium, an advanced glycation end-product cross-link breaker, has been shown to reduce arterial stiffness in elderly subjects. Alagebrium is an AGE-lowering agent with beneficial effects in renal structural and functional parameters in diabetes, decreased diabetes-accelerated atherosclerosis, and age-related myocardial stiffening. ALT-711 exhibits a structural homology to thiamine, and it was suggested to interfere with thiamine metabolism. Enzyme kinetic experiments showed that ALT-711 dose-dependently decreased TDPK activity with K(i)s, calculated by different experiments and fitting models ranging from 0.88 to 1.09 uM. Alagebrium has been investigated for the treatment and prevention of aging, heart failure, physical activity, diabetic nephropathy, and cardiovascular disease, among others. However, this research has been discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Glycoxidative stress and cardiovascular complications in experimentally-induced diabetes: effects of antioxidant treatment. | 2010-11-26 |
|
| Alagebrium chloride, a novel advanced glycation end-product cross linkage breaker, inhibits neointimal proliferation in a diabetic rat carotid balloon injury model. | 2010-10 |
|
| Deletion of the receptor for advanced glycation end products reduces glomerulosclerosis and preserves renal function in the diabetic OVE26 mouse. | 2010-08 |
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| Effects of alagebrium, an advanced glycation end-product breaker, in patients with chronic heart failure: study design and baseline characteristics of the BENEFICIAL trial. | 2010-03 |
|
| Disparate effects on renal and oxidative parameters following RAGE deletion, AGE accumulation inhibition, or dietary AGE control in experimental diabetic nephropathy. | 2010-03 |
|
| Alagebrium attenuates acute methylglyoxal-induced glucose intolerance in Sprague-Dawley rats. | 2010-01 |
|
| Modulation of the cellular expression of circulating advanced glycation end-product receptors in type 2 diabetic nephropathy. | 2010 |
|
| Effect of the age cross-link breaker alagebrium on anterior segment physiology, morphology, and ocular age and rage. | 2009-12 |
|
| Advanced glycation end-products (AGEs): a novel therapeutic target for osteoporosis in patients with rheumatoid arthritis. | 2009-08 |
|
| Methylglyoxal-induced mitochondrial dysfunction in vascular smooth muscle cells. | 2009-06-01 |
|
| RAGE-induced cytosolic ROS promote mitochondrial superoxide generation in diabetes. | 2009-04 |
|
| The breakdown of preformed peritoneal advanced glycation end products by intraperitoneal alagebrium. | 2009-01 |
|
| Receptor for advanced glycation end products (RAGE) deficiency attenuates the development of atherosclerosis in diabetes. | 2008-09 |
|
| Reversal of chaperone activity loss of glycated alphaA-crystallin by a crosslink breaker. | 2008-08 |
|
| Effects of cross-link breakers, glycation inhibitors and insulin sensitisers on HDL function and the non-enzymatic glycation of apolipoprotein A-I. | 2008-06 |
|
| The evolution of systolic blood pressure as a strong predictor of cardiovascular risk and the effectiveness of fixed-dose ARB/CCB combinations in lowering levels of this preferential target. | 2008 |
|
| Cross-link breakers as a new therapeutic approach to cardiovascular disease. | 2007-11 |
|
| Endogenous Secretory RAGE as a Novel Biomarker for Metabolic Syndrome and Cardiovascular Diseases. | 2007-09-17 |
|
| Role of the AGE crosslink breaker, alagebrium, as a renoprotective agent in diabetes. | 2007-08 |
|
| Advanced glycation end-products and arterial stiffness in hypertension. | 2007-03 |
|
| Advanced glycation endproduct crosslink breaker (alagebrium) improves endothelial function in patients with isolated systolic hypertension. | 2007-03 |
|
| Combination therapy with the advanced glycation end product cross-link breaker, alagebrium, and angiotensin converting enzyme inhibitors in diabetes: synergy or redundancy? | 2007-02 |
|
| Alagebrium: benefit on peripheral arteries. | 2006-09 |
|
| Aldose reductase pathway inhibition improved vascular and C-fiber functions, allowing for pressure-induced vasodilation restoration during severe diabetic neuropathy. | 2006-05 |
|
| Preservation of pressure-induced cutaneous vasodilation by limiting oxidative stress in short-term diabetic mice. | 2006-01 |
|
| Beneficial effect of low ethanol intake on the cardiovascular system: possible biochemical mechanisms. | 2006 |
|
| Prevention and reversal of diabetic nephropathy in db/db mice treated with alagebrium (ALT-711). | 2006 |
|
| Extracellular glycation crosslinks: prospects for removal. | 2006 |
|
| The next generation of diabetic nephropathy therapies: an update. | 2005-04 |
|
| The effect of alagebrium chloride (ALT-711), a novel glucose cross-link breaker, in the treatment of elderly patients with diastolic heart failure. | 2005-04 |
|
| Advanced glycation end-product cross-link breakers. A novel approach to cardiovascular pathologies related to the aging process. | 2004-12 |
Patents
Sample Use Guides
One hundred and two patients with heart failure (78% male, aged 62 ± 11 years), and a left ventricular ejection fraction (LVEF) ≤0.45, were randomized to either 200 mg alagebrium twice daily or placebo.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:27:03 GMT 2025
by
admin
on
Mon Mar 31 18:27:03 GMT 2025
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| Record UNII |
79QS8K2877
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C270
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m1466
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PP-36
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