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 |
|---|---|---|
| The next generation of diabetic nephropathy therapies: an update. | 2005 Apr |
|
| The effect of alagebrium chloride (ALT-711), a novel glucose cross-link breaker, in the treatment of elderly patients with diastolic heart failure. | 2005 Apr |
|
| 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 |
|
| Preservation of pressure-induced cutaneous vasodilation by limiting oxidative stress in short-term diabetic mice. | 2006 Jan |
|
| Aldose reductase pathway inhibition improved vascular and C-fiber functions, allowing for pressure-induced vasodilation restoration during severe diabetic neuropathy. | 2006 May |
|
| Alagebrium: benefit on peripheral arteries. | 2006 Sep |
|
| Extracellular glycation crosslinks: prospects for removal. | 2006 Summer |
|
| Role of the AGE crosslink breaker, alagebrium, as a renoprotective agent in diabetes. | 2007 Aug |
|
| Combination therapy with the advanced glycation end product cross-link breaker, alagebrium, and angiotensin converting enzyme inhibitors in diabetes: synergy or redundancy? | 2007 Feb |
|
| Advanced glycation end-products and arterial stiffness in hypertension. | 2007 Mar |
|
| Advanced glycation endproduct crosslink breaker (alagebrium) improves endothelial function in patients with isolated systolic hypertension. | 2007 Mar |
|
| Cross-link breakers as a new therapeutic approach to cardiovascular disease. | 2007 Nov |
|
| Endogenous Secretory RAGE as a Novel Biomarker for Metabolic Syndrome and Cardiovascular Diseases. | 2007 Sep 17 |
|
| 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 |
|
| Reversal of chaperone activity loss of glycated alphaA-crystallin by a crosslink breaker. | 2008 Aug |
|
| Effects of cross-link breakers, glycation inhibitors and insulin sensitisers on HDL function and the non-enzymatic glycation of apolipoprotein A-I. | 2008 Jun |
|
| Receptor for advanced glycation end products (RAGE) deficiency attenuates the development of atherosclerosis in diabetes. | 2008 Sep |
|
| RAGE-induced cytosolic ROS promote mitochondrial superoxide generation in diabetes. | 2009 Apr |
|
| Advanced glycation end-products (AGEs): a novel therapeutic target for osteoporosis in patients with rheumatoid arthritis. | 2009 Aug |
|
| Effect of the age cross-link breaker alagebrium on anterior segment physiology, morphology, and ocular age and rage. | 2009 Dec |
|
| The breakdown of preformed peritoneal advanced glycation end products by intraperitoneal alagebrium. | 2009 Jan |
|
| Methylglyoxal-induced mitochondrial dysfunction in vascular smooth muscle cells. | 2009 Jun 1 |
|
| Modulation of the cellular expression of circulating advanced glycation end-product receptors in type 2 diabetic nephropathy. | 2010 |
|
| Deletion of the receptor for advanced glycation end products reduces glomerulosclerosis and preserves renal function in the diabetic OVE26 mouse. | 2010 Aug |
|
| Alagebrium attenuates acute methylglyoxal-induced glucose intolerance in Sprague-Dawley rats. | 2010 Jan |
|
| 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 Mar |
|
| Disparate effects on renal and oxidative parameters following RAGE deletion, AGE accumulation inhibition, or dietary AGE control in experimental diabetic nephropathy. | 2010 Mar |
|
| Glycoxidative stress and cardiovascular complications in experimentally-induced diabetes: effects of antioxidant treatment. | 2010 Nov 26 |
|
| Alagebrium chloride, a novel advanced glycation end-product cross linkage breaker, inhibits neointimal proliferation in a diabetic rat carotid balloon injury model. | 2010 Oct |
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
Fri Dec 15 16:24:24 UTC 2023
by
admin
on
Fri Dec 15 16:24:24 UTC 2023
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| Record UNII |
79QS8K2877
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| Record Status |
Validated (UNII)
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C270
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CHEMBL2111081
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216306
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C75185
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DTXSID60955648
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300000034109
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m1466
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PP-36
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