Alagebrium bromide | CAS#181069-80-7 | cross-link breaker

MedKoo Cat#: 592433 | Name: Alagebrium bromide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Alagebrium is an advanced glycation endproducts (AGE) cross-link breaker.

Chemical Structure

Alagebrium bromide

CAS#181069-80-7 (bromide)

Theoretical Analysis

MedKoo Cat#: 592433

Name: Alagebrium bromide

CAS#: 181069-80-7 (bromide)

Chemical Formula: C13H14BrNOS

Exact Mass: 232.0791

Molecular Weight: 312.23

Elemental Analysis: C, 50.01; H, 4.52; Br, 25.59; N, 4.49; O, 5.12; S, 10.27

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

181069-80-7 (bromide) 393121-34-1 (cation) 341028-37-3 (chloride)

Synonym

Alagebrium bromide; ALT711; ALT-711; ALT 711.

IUPAC/Chemical Name

Thiazolium, 4,5-dimethyl-3-(2-oxo-2-phenylethyl)- bromide

InChi Key

NWYBJPXXICNVLX-UHFFFAOYSA-M

InChi Code

InChI=1S/C13H14NOS.BrH/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

SMILES Code

O=C(C1=CC=CC=C1)C[N+]2=CSC(C)=C2C.[Br-]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 312.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Mabkhot YN, Alharbi MM, Al-Showiman SS, Ghabbour HA, Kheder NA, Soliman SM, Frey W. Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents. Chem Cent J. 2018 May 11;12(1):56. doi: 10.1186/s13065-018-0420-7. PubMed PMID: 29748782; PubMed Central PMCID: PMC5945573. 2: Toprak C, Sirmagul B, Yigitaslan S. Functional Effects of Alagebrium (ALT-711)-Isolated Rat Carotid Artery. Eurasian J Med. 2017 Oct;49(3):188-192. doi: 10.5152/eurasianjmed.2017.17046. PubMed PMID: 29123442; PubMed Central PMCID: PMC5665628. 3: Prasad K, Mishra M. Do Advanced Glycation End Products and Its Receptor Play a Role in Pathophysiology of Hypertension? Int J Angiol. 2017 Mar;26(1):1-11. doi: 10.1055/s-0037-1598183. Epub 2017 Feb 3. Review. PubMed PMID: 28255209; PubMed Central PMCID: PMC5330762. 4: Kim J, Kim CS, Kim YS, Lee IS, Kim JS. Jakyakgamcho-tang and Its Major Component, Paeonia Lactiflora, Exhibit Potent Anti-glycation Properties. J Exerc Nutrition Biochem. 2016 Dec 31;20(4):60-64. doi: 10.20463/jenb.2016.0049. PubMed PMID: 28150470; PubMed Central PMCID: PMC5545203. 5: Li S, Ding YF, Yin H, Wang C, Bardelang D, Wang LH, Wang R. Encapsulation of AGE-Breaker Alagebrium by Cucurbit[7]uril Improved the Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen. Chem Asian J. 2016 Nov 7;11(21):3126-3133. doi: 10.1002/asia.201601153. Epub 2016 Oct 12. PubMed PMID: 27605465. 6: Dhar A, Udumula MP, Medapi B, Bhat A, Dhar I, Malapati P, Babu MS, Kalra J, Sriram D, Desai KM. Pharmacological evaluation of novel alagebrium analogs as methylglyoxal scavengers in vitro in cardiac myocytes and in vivo in SD rats. Int J Cardiol. 2016 Nov 15;223:581-589. doi: 10.1016/j.ijcard.2016.08.243. Epub 2016 Aug 15. PubMed PMID: 27561164. 7: Carrick-Ranson G, Fujimoto N, Shafer KM, Hastings JL, Shibata S, Palmer MD, Boyd K, Levine BD. The effect of 1 year of Alagebrium and moderate-intensity exercise training on left ventricular function during exercise in seniors: a randomized controlled trial. J Appl Physiol (1985). 2016 Aug 1;121(2):528-36. doi: 10.1152/japplphysiol.00021.2016. Epub 2016 Jul 8. PubMed PMID: 27402556. 8: Borg DJ, Forbes JM. Targeting advanced glycation with pharmaceutical agents: where are we now? Glycoconj J. 2016 Aug;33(4):653-70. doi: 10.1007/s10719-016-9691-1. Epub 2016 Jul 9. Review. PubMed PMID: 27392438. 9: Atlı Ö, Ilgın S, Ergun B, Burukoğlu D, Musmul A, Sırmagül B. Matrix metalloproteinases are possible targets in monocrotaline-induced pulmonary hypertension: investigation of anti-remodeling effects of alagebrium and everolimus. Anatol J Cardiol. 2017 Jan;17(1):8-17. doi: 10.14744/AnatolJCardiol.2016.6891. Epub 2016 Apr 26. PubMed PMID: 27182612; PubMed Central PMCID: PMC5324875. 10: Nenna A, Nappi F, Chello M, Spadaccio C. Targeting Advanced Glycation End Products in Cardiac Surgery: The Unexplored Alternative. Res Cardiovasc Med. 2016 Mar 5;5(2):e31707. doi: 10.5812/cardiovascmed.31707. eCollection 2016 May. PubMed PMID: 26949696; PubMed Central PMCID: PMC4756255. 11: Dhar A, Dhar I, Bhat A, Desai KM. Alagebrium attenuates methylglyoxal induced oxidative stress and AGE formation in H9C2 cardiac myocytes. Life Sci. 2016 Feb 1;146:8-14. doi: 10.1016/j.lfs.2016.01.006. Epub 2016 Jan 6. PubMed PMID: 26772824. 12: Chiu CY, Yang RS, Sheu ML, Chan DC, Yang TH, Tsai KS, Chiang CK, Liu SH. Advanced glycation end-products induce skeletal muscle atrophy and dysfunction in diabetic mice via a RAGE-mediated, AMPK-down-regulated, Akt pathway. J Pathol. 2016 Feb;238(3):470-82. doi: 10.1002/path.4674. Epub 2015 Dec 31. PubMed PMID: 26586640. 13: Siegman MJ, Eto M, Butler TM. Remodeling of the rat distal colon in diabetes: function and ultrastructure. Am J Physiol Cell Physiol. 2016 Jan 15;310(2):C151-60. doi: 10.1152/ajpcell.00253.2015. Epub 2015 Nov 11. PubMed PMID: 26561639; PubMed Central PMCID: PMC4719031. 14: Fischer T. [Pharmacological therapy of age-related macular degeneration based on etiopathogenesis]. Orv Hetil. 2015 Nov 15;156(46):1847-58. doi: 10.1556/650.2015.30207. Review. Hungarian. PubMed PMID: 26548469. 15: Zakaria MN, El-Bassossy HM, Barakat W. Targeting AGEs Signaling Ameliorates Central Nervous System Diabetic Complications in Rats. Adv Pharmacol Sci. 2015;2015:346259. doi: 10.1155/2015/346259. Epub 2015 Sep 29. PubMed PMID: 26491434; PubMed Central PMCID: PMC4603311. 16: Nenna A, Nappi F, Avtaar Singh SS, Sutherland FW, Di Domenico F, Chello M, Spadaccio C. Pharmacologic Approaches Against Advanced Glycation End Products (AGEs) in Diabetic Cardiovascular Disease. Res Cardiovasc Med. 2015 May 23;4(2):e26949. doi: 10.5812/cardiovascmed.4(2)2015.26949. eCollection 2015 May. Review. PubMed PMID: 26393232; PubMed Central PMCID: PMC4571620. 17: Wang H, Weihrauch D, Kersten JR, Toth JM, Passerini AG, Rajamani A, Schrepfer S, LaDisa JF Jr. Alagebrium inhibits neointimal hyperplasia and restores distributions of wall shear stress by reducing downstream vascular resistance in obese and diabetic rats. Am J Physiol Heart Circ Physiol. 2015 Oct;309(7):H1130-40. doi: 10.1152/ajpheart.00123.2014. Epub 2015 Aug 7. PubMed PMID: 26254329; PubMed Central PMCID: PMC4865061. 18: Cadau S, Leoty-Okombi S, Pain S, Bechetoille N, André-Frei V, Berthod F. In vitro glycation of an endothelialized and innervated tissue-engineered skin to screen anti-AGE molecules. Biomaterials. 2015 May;51:216-225. doi: 10.1016/j.biomaterials.2015.01.066. Epub 2015 Feb 19. PubMed PMID: 25771012. 19: Kim J, Kim CS, Moon MK, Kim JS. Epicatechin breaks preformed glycated serum albumin and reverses the retinal accumulation of advanced glycation end products. Eur J Pharmacol. 2015 Feb 5;748:108-14. doi: 10.1016/j.ejphar.2014.12.010. Epub 2014 Dec 19. PubMed PMID: 25530268. 20: Miyamoto M, Kotani K, Taniguchi N. Effect of non-antihypertensive drugs on endothelial function in hypertensive subjects evaluated by flow-mediated vasodilation. Curr Vasc Pharmacol. 2015;13(1):121-7. Review. PubMed PMID: 25440598.