Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H14NOS |
Molecular Weight | 232.321 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 1 |
SHOW SMILES / InChI
SMILES
CC1=C(C)[N+](CC(=O)C2=CC=CC=C2)=CS1
InChI
InChIKey=LYLFQLCLUXOFOL-UHFFFAOYSA-N
InChI=1S/C13H14NOS/c1-10-11(2)16-9-14(10)8-13(15)12-6-4-3-5-7-12/h3-7,9H,8H2,1-2H3/q+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 |
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Advanced glycation end-product Sources: https://www.ncbi.nlm.nih.gov/pubmed/24965174 |
PubMed
Title | Date | PubMed |
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Advanced glycation end-product cross-link breakers. A novel approach to cardiovascular pathologies related to the aging process. | 2004 Dec |
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Beneficial effect of low ethanol intake on the cardiovascular system: possible biochemical mechanisms. | 2006 |
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Prevention and reversal of diabetic nephropathy in db/db mice treated with alagebrium (ALT-711). | 2006 |
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Advanced glycation end-products and arterial stiffness in hypertension. | 2007 Mar |
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Advanced glycation endproduct crosslink breaker (alagebrium) improves endothelial function in patients with isolated systolic hypertension. | 2007 Mar |
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Cross-link breakers as a new therapeutic approach to cardiovascular disease. | 2007 Nov |
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Endogenous Secretory RAGE as a Novel Biomarker for Metabolic Syndrome and Cardiovascular Diseases. | 2007 Sep 17 |
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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 |
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Effects of cross-link breakers, glycation inhibitors and insulin sensitisers on HDL function and the non-enzymatic glycation of apolipoprotein A-I. | 2008 Jun |
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RAGE-induced cytosolic ROS promote mitochondrial superoxide generation in diabetes. | 2009 Apr |
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Advanced glycation end-products (AGEs): a novel therapeutic target for osteoporosis in patients with rheumatoid arthritis. | 2009 Aug |
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Modulation of the cellular expression of circulating advanced glycation end-product receptors in type 2 diabetic nephropathy. | 2010 |
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Deletion of the receptor for advanced glycation end products reduces glomerulosclerosis and preserves renal function in the diabetic OVE26 mouse. | 2010 Aug |
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Alagebrium attenuates acute methylglyoxal-induced glucose intolerance in Sprague-Dawley rats. | 2010 Jan |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21669961
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21088756
Rat aortic vascular smooth muscle cells (RASMCs) were treated with 1-100 uM of alagebrium added 24 hours before the addition of AGEs.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:03:25 UTC 2023
by
admin
on
Fri Dec 15 16:03:25 UTC 2023
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Record UNII |
DGH49JXB1F
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Record Status |
Validated (UNII)
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Record Version |
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-
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ALAGEBRIUM
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admin on Fri Dec 15 16:03:25 UTC 2023 , Edited by admin on Fri Dec 15 16:03:25 UTC 2023
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DGH49JXB1F
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admin on Fri Dec 15 16:03:25 UTC 2023 , Edited by admin on Fri Dec 15 16:03:25 UTC 2023
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216305
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DTXSID00192550
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DB12497
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393121-34-1
Created by
admin on Fri Dec 15 16:03:25 UTC 2023 , Edited by admin on Fri Dec 15 16:03:25 UTC 2023
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |