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Alagebrium
Chemical compound
Chemical compound
| Field | Value | |||||
|---|---|---|---|---|---|---|
| Verifiedfields | changed | |||||
| verifiedrevid | 477316280 | |||||
| IUPAC_name | 4,5-dimethyl-3-(2-oxo-2-phenylethyl)-thiazolium chloride | |||||
| image | Alagebrium_structure.svg | |||||
| image_class | skin-invert-image | |||||
| image2 | Alagebrium sf.png | |||||
| image_class2 | bg-transparent | |||||
| pregnancy_AU | ||||||
| pregnancy_US | ||||||
| legal_AU | ||||||
| legal_CA | ||||||
| legal_UK | ||||||
| legal_US | ||||||
| CAS_number_Ref | ||||||
| CAS_number | 393121-34-1 | |||||
| ATC_prefix | none | |||||
| PubChem | 216306 | |||||
| DrugBank_Ref | ||||||
| ChemSpiderID_Ref | ||||||
| ChemSpiderID | 187495 | |||||
| ChEMBL_Ref | ||||||
| ChEMBL | 2107309 | |||||
| UNII_Ref | ||||||
| UNII | DGH49JXB1F | |||||
| index2_label | as chloride | |||||
| CAS_number2_Ref | ||||||
| CAS_number2 | 341028-37-3 | |||||
| UNII2_Ref | ||||||
| UNII2 | 79QS8K2877 | |||||
| C | 13 | H=14 | Cl=1 | N=1 | O=1 | S=1 |
| smiles | [Cl-].O=C(c1ccccc1)C[n+]2c(c(sc2)C)C | |||||
| StdInChI_Ref | ||||||
| StdInChI | 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 | |||||
| StdInChIKey_Ref | ||||||
| StdInChIKey | MKOMESMZHZNBIZ-UHFFFAOYSA-M |
Alagebrium (formerly known as ALT-711, dimethyl-3-N-phenacylthiazolium chloride) was a drug candidate developed by Alteon, Inc. It was the first drug candidate to be clinically tested for the purpose of breaking the crosslinks caused by advanced glycation endproducts (AGEs), thereby reversing one of the main mechanisms of aging. Through this effect Alagebrium is designed to reverse the stiffening of blood vessel walls that contributes to hypertension and cardiovascular disease, as well as many other forms of degradation associated with protein crosslinking. Alagebrium has proven effective in reducing systolic blood pressure and providing therapeutic benefit for patients with diastolic heart failure.
Mechanism
Advanced glycation end-products (AGEs) are proteins that become glycated as a result of exposure to sugars. They are a bio-marker implicated in aging and the development, or worsening, of many degenerative diseases, such as diabetes, atherosclerosis, chronic kidney disease, and Alzheimer's disease. Pharmacologic intervention with alagebrium directly targets the biochemical pathway leading to AGEs. Although alagebrium may break some important AGE crosslinks, there is no evidence that it is effective against the most prevalent crosslink: glucosepane.
History
Alteon said that it had selected ALT-711 as its lead AGE-breaker based on preclinical results in its annual report for the year 1997 and that it was preparing an IND filing.
The INN name was proposed in 2004 and recommended in 2005.
In 2006 Alteon merged with a company called HaptoGuard that had cash and a potential diagnostic test for haptoglobin; as part of the merger Genentech, which held preferred shares in Alteon, converted their shares to common ones and received the right to get milestone payments and royalties on sales of alagebrium, and option rights to license ALT-2074. Synvista announced that it was terminating clinical trials of alagebrium in January 2009 in order to focus on the diagnostic test and another clinical candidate SYI-2074 (formerly ALT-2074). The company seems to have discontinued operations and their website is no longer available.
References
References
- "R&D overview: A.G.E. crosslink breakers and Alagebrium". Alteon Corporation.
- "Product Candidate: A.G.E. crosslink breakers". Alteon Corporation.
- (December 2004). "Advanced glycation end-product cross-link breakers. A novel approach to cardiovascular pathologies related to the aging process". American Journal of Hypertension.
- (April 2005). "The effect of alagebrium chloride (ALT-711), a novel glucose cross-link breaker, in the treatment of elderly patients with diastolic heart failure". Journal of Cardiac Failure.
- (August 2006). "Advanced glycation end products: sparking the development of diabetic vascular injury". Circulation.
- (2006). "Prevention and repair of protein damage by the Maillard reaction in vivo". Rejuvenation Research.
- (31 March 1998). "Alteon 10-K For the fiscal year ended December 31, 1997". Alteon via SEC Edgar.
- (2004). "Proposed INN: List 91". WHO Drug Information.
- (2005). "Recommended INN: List 53". WHO Drug Information.
- (15 March 2008). "10-K For the fiscal year ended December 31, 2007". U.S. Securities and Exchange Commission.
- (29 January 2009). "Synvista Therapeutics Announces Termination of Clinical Trials of Alagebrium and SYI-2074 and Provides Business Update". FierceBiotech.
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