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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
DGH49JXB1F
Record Status Validated (UNII)
Record Version