For research use only. Not for therapeutic Use.
Oxfenicine is a carnitine palmitoyltransferase I (CPT-1) inhibitor involved in fatty acid metabolism in the heart. In animal studies oxfenicine acts as a cardioprotective agent during ischemia. Oxfenicine produces changes in myocardial substrate utilisation and is attributed to the protection of ischemic stressed myocardium by shifting the cardiac metabolism with reduction of FFA (Free Fatty Acid) utilisation. This may be favourable in circumstances with limited oxygen supply.
| Catalog Number | R043847 |
| CAS Number | 32462-30-9 |
| Synonyms | (αS)-α-Amino-4-hydroxy-benzeneacetic Acid; (S)-α-Amino-4-hydroxy-benzeneacetic Acid; L-2-(p-Hydroxyphenyl)-glycine; (S)-(4-Hydroxyphenyl)glycine; (S)-2-(4-Hydroxyphenyl)glycine; (S)-2-Amino-2-(4-hydroxyphenyl)acetic Acid; L-(+)-(p-Hydroxyphenyl)glyci |
| Molecular Formula | C8H9NO3 |
| Purity | ≥95% |
| Storage | -20°C |
| IUPAC Name | (2S)-2-amino-2-(4-hydroxyphenyl)acetic acid |
| InChI | InChI=1S/C8H9NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h1-4,7,10H,9H2,(H,11,12)/t7-/m0/s1 |
| InChIKey | LJCWONGJFPCTTL-ZETCQYMHSA-N |
| SMILES | C1=CC(=CC=C1C(C(=O)O)N)O |
| Reference | </br>1: Wang CH, Wang SS, Ko WJ, Chen YS, Chang CY, Chang RW, Chang KC. Acetyl-l-carnitine and oxfenicine on cardiac pumping mechanics in streptozotocin-induced diabetes in male Wistar rats. PLoS One. 2013 Jul 26;8(7):e69977. doi: 10.1371/journal.pone.0069977. Print 2013. PubMed PMID: 23922880; PubMed Central PMCID: PMC3724909.</br> 2: Chang KC, Tseng CD, Lu SC, Liang JT, Wu MS, Tsai MS, Hsu KL. Effects of acetyl-L-carnitine and oxfenicine on aorta stiffness in diabetic rats. Eur J Clin Invest. 2010 Nov;40(11):1002-10. doi: 10.1111/j.1365-2362.2010.02358.x. PubMed PMID: 20678118.</br> 3: Angsten G, Valind S, Takalo R, Neu H, Meurling S, Långström B. Inhibition of carnitine-acyl transferase I by oxfenicine studied in vivo with [11C]-labeled fatty acids. Nucl Med Biol. 2005 Jul;32(5):495-503. PubMed PMID: 15982580.</br> 4: Meehan AG, Higgins AJ. Oleate plus oxfenicine improves functional recovery, assessed via an intraventricular balloon, in ischemic-reperfused rat hearts. Ann N Y Acad Sci. 1994 Jun 17;723:343-4. PubMed PMID: 8030880.</br> 5: Stephens TW, Higgins AJ, Cook GA, Harris RA. Two mechanisms produce tissue-specific inhibition of fatty acid oxidation by oxfenicine. Biochem J. 1985 Apr 15;227(2):651-60. PubMed PMID: 4004784; PubMed Central PMCID: PMC1144885.</br> 6: Korb H, Hoeft A, Hunneman DH, Schraeder R, Wolpers HG, Wober W, Hellige G. Changes in myocardial substrate utilisation and protection of ischemic stressed myocardium by oxfenicine [(S)-4-hydroxyphenylglycine]. Naunyn Schmiedebergs Arch Pharmacol. 1984 Aug;327(1):70-4. PubMed PMID: 6493353.</br> 7: Drake-Holland AJ, Passingham JE. The effect of Oxfenicine on cardiac carbohydrate metabolism in intact dogs. Basic Res Cardiol. 1983 Jan-Feb;78(1):19-27. PubMed PMID: 6847579.</br> 8: Burges RA, Gardiner DG, Higgins AJ. Protection of the ischaemic dog heart by oxfenicine. Life Sci. 1981 Nov 2;29(18):1847-53. PubMed PMID: 7311718.</br> 9: Higgins AJ, Morville M, Burges RA, Blackburn KJ. Mechanism of action of oxfenicine on muscle metabolism. Biochem Biophys Res Commun. 1981 May 15;100(1):291-6. PubMed PMID: 7259751.</br> 10: Higgins AJ, Morville M, Burges RA, Gardiner DG, Page MG, Blackburn KJ. Oxfenicine diverts rat muscle metabolism from fatty acid to carbohydrate oxidation and protects the ischaemic rat heart. Life Sci. 1980 Sep 15;27(11):963-70. PubMed PMID: 7432098.</br> 11: Naqvi N, Thompson DS, Juul SM, Jenkins BS, Webb-Peploe MM, Coltart DJ. Stimulation of myocardial lactate extraction by oxfenicine (L-hydroxyphenylglycine). Eur Heart J. 1980 Aug;1(4):255-61. PubMed PMID: 7274236.</br> 12: Marina Prendes MG, García JV, Testoni G, Fernández MA, Perazzo JC, Savino EA, Varela A. Influence of fasting on the effects of dimethylamiloride and oxfenicine on ischaemic-reperfused rat hearts. Arch Physiol Biochem. 2006 Feb;112(1):31-6. PubMed PMID: 16754201.</br> 13: Kennedy JA, Kiosoglous AJ, Murphy GA, Pelle MA, Horowitz JD. Effect of perhexiline and oxfenicine on myocardial function and metabolism during low-flow ischemia/reperfusion in the isolated rat heart. J Cardiovasc Pharmacol. 2000 Dec;36(6):794-801. PubMed PMID: 11117381.</br> 14: Varela A, Carregal M, Testoni G, Dalamon V, Savino EA. Effects of fasting, hypoxia, methylpalmoxirate and oxfenicine on the tissue-levels of long-chain acyl CoA and acylcarnitine in the rat atria. Arch Physiol Biochem. 1997 Oct;105(6):572-6. PubMed PMID: 9587648.</br> 15: Carregal M, Varela A, Dalamon V, Sacks S, Savino EA. Beneficial effects of oxfenicine on the hypoxic rat atria. Arch Physiol Biochem. 1995 Apr;103(1):45-9. PubMed PMID: 8574776.</br> 16: Varela A, Carregal M, Espósito S, Bruno-Magnasco C, Savino EA. Effects of oxfenicine on the atria from fed and fasted rats. Arch Int Physiol Biochim Biophys. 1994 Mar-Apr;102(2):125-8. PubMed PMID: 7519459.</br> 17: Jodalen H, Ytrehus K, Moen P, Hokland B, Mjøs OD. Oxfenicine-induced accumulation of lipid in the rat myocardium. J Mol Cell Cardiol. 1988 Mar;20(3):277-82. PubMed PMID: 3398058.</br> 18: Bachmann E, Weber E. Biochemical mechanisms of oxfenicine cardiotoxicity. Pharmacology. 1988;36(4):238-48. PubMed PMID: 2967979.</br> 19: Molaparast-Saless F, Liedtke AJ, Nellis SH. Effects of the fatty acid blocking agents, oxfenicine and 4-bromocrotonic acid, on performance in aerobic and ischemic myocardium. J Mol Cell Cardiol. 1987 May;19(5):509-20. PubMed PMID: 3625784.</br> 20: Bielefeld DR, Vary TC, Neely JR. Inhibition of carnitine palmitoyl-CoA transferase activity and fatty acid oxidation by lactate and oxfenicine in cardiac muscle. J Mol Cell Cardiol. 1985 Jun;17(6):619-25. PubMed PMID: 3927008.</br></br> |
