U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ALAGEBRIUM

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Advanced glycation end-product
PubMed

PubMed

TitleDatePubMed
Advanced glycation end-product cross-link breakers. A novel approach to cardiovascular pathologies related to the aging process.
2004 Dec
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
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
Effects of cross-link breakers, glycation inhibitors and insulin sensitisers on HDL function and the non-enzymatic glycation of apolipoprotein A-I.
2008 Jun
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
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
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

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
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 Fri Dec 15 16:03:25 UTC 2023
Edited
by admin
on Fri Dec 15 16:03:25 UTC 2023
Record UNII
DGH49JXB1F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALAGEBRIUM
Common Name English
ALAGEBRIUM CATION
Common Name English
THIAZOLIUM, 4,5-DIMETHYL-3-(2-OXO-2-PHENYLETHYL)-
Systematic Name English
ALAGEBRIUM ION
Common Name English
4,5-DIMETHYL-3-(2-OXO-2-PHENYLETHYL)-1,3-THIAZOL-3-IUM
Systematic Name English
Code System Code Type Description
WIKIPEDIA
ALAGEBRIUM
Created by admin on Fri Dec 15 16:03:25 UTC 2023 , Edited by admin on Fri Dec 15 16:03:25 UTC 2023
PRIMARY
FDA UNII
DGH49JXB1F
Created by admin on Fri Dec 15 16:03:25 UTC 2023 , Edited by admin on Fri Dec 15 16:03:25 UTC 2023
PRIMARY
PUBCHEM
216305
Created by admin on Fri Dec 15 16:03:25 UTC 2023 , Edited by admin on Fri Dec 15 16:03:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID00192550
Created by admin on Fri Dec 15 16:03:25 UTC 2023 , Edited by admin on Fri Dec 15 16:03:25 UTC 2023
PRIMARY
DRUG BANK
DB12497
Created by admin on Fri Dec 15 16:03:25 UTC 2023 , Edited by admin on Fri Dec 15 16:03:25 UTC 2023
PRIMARY
CAS
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
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY