Oxfenicine
featured

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

MedKoo CAT#: 525808

CAS#: 32462-30-9

Description: Oxfenicine, also known as UK-25842, 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.

Chemical Structure

img
Oxfenicine
CAS# 32462-30-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525808
Name: Oxfenicine
CAS#: 32462-30-9
Chemical Formula: C8H9NO3
Exact Mass: 167.06
Molecular Weight: 167.160
Elemental Analysis: C, 57.48; H, 5.43; N, 8.38; O, 28.71

Price and Availability

Size Price Availability Quantity
1g USD 90 Ready to ship
2g USD 150 Ready to ship
5g USD 250 Ready to ship
10g USD 400 Ready to ship
25g USD 650 2 weeks
50g USD 850 2 Weeks
Bulk inquiry

Synonym: UK-25,842; UK 25,842; UK25,842; UK-25842; UK 25842; UK25842; Oxfenicina; Oxfenicinum; Oxfenicine

IUPAC/Chemical Name: (S)-2-amino-2-(4-hydroxyphenyl)acetic acid

InChi Key: LJCWONGJFPCTTL-ZETCQYMHSA-N

InChi Code: 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

SMILES Code: O=C(O)[C@@H](N)C1=CC=C(O)C=C1

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: >2 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: 2934.99.9001

More Info:

Product Data:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot#T7C09I15
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Oxfenicine (L-p-Hydroxyphenylglycine) is a carnitine palmitoyltransferase-1 inhibitor that inhibits the oxidation of fatty acid in heart. Oxfenicine protects heart from necrotic tissue damage during ischaemia
In vitro activity: This study is the first to examine the in vitro effects of oxfenicine-induced CPT-1b inhibition on adipocyte metabolism In isolated adipocytes from both the Epid and SC Ing fat depots treated with 1 mM oxfenicine, palmitate oxidation was significantly reduced by 50% compared with control cells (Fig. 6, A and B). Isoproterenol-stimulated lipolysis was significantly decreased by 20% and 12% in Epid adipocytes following treatment with 100 μM and 1 mM oxfenicine, respectively (Fig. 6C). Similarly, in SC Ing adipocytes treatment with 100 μM and 1 mM of oxfenicine decreased stimulated lipolysis by 8% and 18%, respectively (Fig. 6D). There was no effect of oxfenicine on basal rates of lipolysis in Epid and SC Ing adipocytes (Fig. 6, C and D). Basal and insulin-stimulated glucose incorporation into lipids, the measure for lipogenesis, was reduced by 39% and 31%, respectively, in Epid adipocytes following treatment with 1 mM oxfenicine (Fig. 7A). In adipocytes from the SC Ing fat depot, the incorporation of glucose into lipids was also reduced by 41% under insulin-stimulated conditions, following 1 mM oxfenicine treatment (Fig. 7B). This suggests that fat cells adjusted their metabolism to compensate for the increased circulating NEFAs seen with inhibition of β-oxidation. Reference: Am J Physiol Regul Integr Comp Physiol. 2016 Oct 1; 311(4): R779–R787. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5142162/
In vivo activity: This study investigated whether oxfenicine-induced inhibition of FA oxidation affected adiposity and WAT metabolism in rats fed either low (LF) or high-fat (HF) diets. Following 8 wk of dietary intervention, male Sprague-Dawley rats were given a daily intraperitoneal injection of oxfenicine (150 mg/kg body wt) or vehicle (PBS) for 3 wk. To examine the in vivo effects of the oxfenicine treatment, animals were placed in the CLAMS for 24 h following oxfenicine treatment and their V̇ o2, ambulatory activity, and respiratory exchange ratio (RER) were measured. Treatment with oxfenicine had no effect on the RER of animals fed the LF diet, whereas those fed a HF diet had significantly higher RER values, particularly during the dark cycle (Fig. 1, C and D). This is indicative of the effectiveness of oxfenicine at inhibiting fatty acid β-oxidation, resulting in an increased reliance on carbohydrate oxidation. This was more pronounced during the dark cycle (1900 to 0700), when the animals were the most active and ate the most food (0.830 ± 0.00271 V̇ co2/V̇ o2 vs. 0.796 ± 0.00244, V̇ co2/V̇ o2, Fig. 1, C and D). Fasting plasma NEFAs were also 1.45- and 1.46fold higher in the LF- and HF-fed animals, respectively, following 3 wk of oxfenicine treatment (Fig. 1E). An increase in circulating fatty acids provides further evidence of the effectiveness of the oxfenicine treatment in reducing fatty acid oxidation. This is the first study to examine the adaptive changes in adipose tissue metabolism that occur as a result of suppressing fatty acid oxidation through CPT-1b inhibition in vivo and provides novel additional information regarding this potential obesity and T2D therapy. Reference: Am J Physiol Regul Integr Comp Physiol. 2016 Oct 1; 311(4): R779–R787. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5142162/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 4.6 27.22
H2O 1.0 5.98
DMSO 4.6 27.22
H2O 1.0 5.98

Preparing Stock Solutions

The following data is based on the product molecular weight 167.16 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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Sepa-Kishi DM, Wu MV, Uthayakumar A, Mohasses A, Ceddia RB. Antilipolytic and antilipogenic effects of the CPT-1b inhibitor oxfenicine in the white adipose tissue of rats. Am J Physiol Regul Integr Comp Physiol. 2016 Oct 1;311(4):R779-R787. doi: 10.1152/ajpregu.00243.2016. Epub 2016 Aug 24. PMID: 27558315; PMCID: PMC5142162 2. 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. doi: 10.1007/BF01923190. PMID: 6847579.
In vitro protocol: 1. Sepa-Kishi DM, Wu MV, Uthayakumar A, Mohasses A, Ceddia RB. Antilipolytic and antilipogenic effects of the CPT-1b inhibitor oxfenicine in the white adipose tissue of rats. Am J Physiol Regul Integr Comp Physiol. 2016 Oct 1;311(4):R779-R787. doi: 10.1152/ajpregu.00243.2016. Epub 2016 Aug 24. PMID: 27558315; PMCID: PMC5142162
In vivo protocol: 1. Sepa-Kishi DM, Wu MV, Uthayakumar A, Mohasses A, Ceddia RB. Antilipolytic and antilipogenic effects of the CPT-1b inhibitor oxfenicine in the white adipose tissue of rats. Am J Physiol Regul Integr Comp Physiol. 2016 Oct 1;311(4):R779-R787. doi: 10.1152/ajpregu.00243.2016. Epub 2016 Aug 24. PMID: 27558315; PMCID: PMC5142162. 2. 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. doi: 10.1007/BF01923190. PMID: 6847579.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
18: Bachmann E, Weber E. Biochemical mechanisms of oxfenicine cardiotoxicity. Pharmacology. 1988;36(4):238-48. PubMed PMID: 2967979.
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.
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.