Etomoxir sodium salt | CAS#828934-41-4 | CPT-1 inhibitor

MedKoo Cat#: 319998 | Name: Etomoxir sodium

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Description:

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

Etomoxir is an irreversible inhibitor of carnitine palmitoyltransferase-1 (CPT-1) on the outer face of the inner mitochondrial membrane. This prevents the formation of acyl carnitines, a step that is necessary for the transport of fatty acyl chains from the cytosol into the intermembrane space of the mitochondria. This step is essential to the production of ATP from fatty acid oxidation. Etomoxir has also been identified as a direct agonist of PPARα.

Chemical Structure

Etomoxir sodium

CAS#828934-41-4 (sodium)

Theoretical Analysis

MedKoo Cat#: 319998

Name: Etomoxir sodium

CAS#: 828934-41-4 (sodium)

Chemical Formula: C15H18ClNaO4

Exact Mass: 0.0000

Molecular Weight: 320.74

Elemental Analysis: C, 56.17; H, 5.66; Cl, 11.05; Na, 7.17; O, 19.95

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 weeks
25mg	USD 650.00	2 weeks

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Related CAS #

828934-41-4 (sodium) 82258-36-4 (racemic) 124083-20-1

Synonym

Etomoxir sodium; B 807-54; B807-54; B-807-54; B 80754; B80754; B-80754;

IUPAC/Chemical Name

(2R)-2-[6-(4-chlorophenoxy)hexyl]-2-oxiranecarboxylic acid monosodium salt

InChi Key

RPACBEVZENYWOL-XFULWGLBSA-M

InChi Code

InChI=1S/C15H19ClO4.Na/c16-12-5-7-13(8-6-12)19-10-4-2-1-3-9-15(11-20-15)14(17)18;/h5-8H,1-4,9-11H2,(H,17,18);/q;+1/p-1/t15-;/m1./s1

SMILES Code

O=C([C@]1(CCCCCCOC2=CC=C(Cl)C=C2)OC1)[O-].[Na+]

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, not in water

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

Instruction

View handling instruction

Biological target:

Etomoxir sodium salt ((R)-(+)-Etomoxir sodium salt) is an irreversible inhibitor of carnitine palmitoyltransferase 1a (CPT-1a), inhibits fatty acid oxidation (FAO) through CPT-1a and inhibits palmitate β-oxidation in human, rat and guinea pig.

In vitro activity:

Inhibition of fatty acid oxidation (FAO) with etomoxir caused lipid accumulation, decreased adenosine triphosphate (ATP) and nicotinamide adenine dinucleotide phosphate (NADPH) levels, suppressed BCa cell growth in vitro and in vivo, and reduced motility of BCa cells via affecting epithelial-mesenchymal transition (EMT)-related proteins. Furthermore, etomoxir induced BCa cell cycle arrest at G0/G1 phase through peroxisome proliferator-activated receptor (PPAR) γ-mediated pathway with alterations in fatty acid metabolism associated gene expression. Reference: Clin Sci (Lond). 2019 Aug 7;133(15):1745-1758. https://pubmed.ncbi.nlm.nih.gov/31358595/

In vivo activity:

Etomoxir-treated mice showed no difference in embryonic morphology; however, etomoxir-treated male gonocytes exited mitotic arrest, and cells of the gonad underwent apoptosis. In addition, etomoxir-treated mice at P7 displayed impaired homing of spermatogonia and increased cell apoptosis. Reference: BMC Dev Biol. 2021 Feb 1;21(1):5. https://pubmed.ncbi.nlm.nih.gov/33517883/

	Solvent	mg/mL	mM
Solubility
	DMSO	32.1	100.08
	DMF	10.0	31.18
	DMF:PBS (pH 7.2) (1:1)	0.5	1.56
	Ethanol	2.0	6.27
	Water	14.5	45.11

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 320.74 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

Formulation protocol:

1. Cheng S, Wang G, Wang Y, Cai L, Qian K, Ju L, Liu X, Xiao Y, Wang X. Fatty acid oxidation inhibitor etomoxir suppresses tumor progression and induces cell cycle arrest via PPARγ-mediated pathway in bladder cancer. Clin Sci (Lond). 2019 Aug 7;133(15):1745-1758. doi: 10.1042/CS20190587. PMID: 31358595. 2. Qiu CC, Atencio AE, Gallucci S. Inhibition of fatty acid metabolism by etomoxir or TOFA suppresses murine dendritic cell activation without affecting viability. Immunopharmacol Immunotoxicol. 2019 Jun;41(3):361-369. doi: 10.1080/08923973.2019.1616754. Epub 2019 Jun 2. PMID: 31155984. 3. Xu Y, Xie J. Etomoxir regulates the differentiation of male germ cells by specifically reducing H3K27ac level. BMC Dev Biol. 2021 Feb 1;21(1):5. doi: 10.1186/s12861-020-00237-x. PMID: 33517883; PMCID: PMC7849134. 4. Schwarzer M, Faerber G, Rueckauer T, Blum D, Pytel G, Mohr FW, Doenst T. The metabolic modulators, Etomoxir and NVP-LAB121, fail to reverse pressure overload induced heart failure in vivo. Basic Res Cardiol. 2009 Sep;104(5):547-57. doi: 10.1007/s00395-009-0015-5. Epub 2009 Mar 14. PMID: 19294446.

In vitro protocol:

In vivo protocol:

1. Xu Y, Xie J. Etomoxir regulates the differentiation of male germ cells by specifically reducing H3K27ac level. BMC Dev Biol. 2021 Feb 1;21(1):5. doi: 10.1186/s12861-020-00237-x. PMID: 33517883; PMCID: PMC7849134. 2. Schwarzer M, Faerber G, Rueckauer T, Blum D, Pytel G, Mohr FW, Doenst T. The metabolic modulators, Etomoxir and NVP-LAB121, fail to reverse pressure overload induced heart failure in vivo. Basic Res Cardiol. 2009 Sep;104(5):547-57. doi: 10.1007/s00395-009-0015-5. Epub 2009 Mar 14. PMID: 19294446.

1: Estañ MC, Calviño E, Calvo S, Guillén-Guío B, Boyano-Adánez Mdel C, de Blas E, Rial E, Aller P. Apoptotic efficacy of etomoxir in human acute myeloid leukemia cells. Cooperation with arsenic trioxide and glycolytic inhibitors, and regulation by oxidative stress and protein kinase activities. PLoS One. 2014 Dec 15;9(12):e115250. doi: 10.1371/journal.pone.0115250. eCollection 2014. PubMed PMID: 25506699; PubMed Central PMCID: PMC4266683. 2: Li J, Zhao S, Zhou X, Zhang T, Zhao L, Miao P, Song S, Sun X, Liu J, Zhao X, Huang G. Inhibition of lipolysis by mercaptoacetate and etomoxir specifically sensitize drug-resistant lung adenocarcinoma cell to paclitaxel. PLoS One. 2013 Sep 11;8(9):e74623. doi: 10.1371/journal.pone.0074623. eCollection 2013. PubMed PMID: 24040298; PubMed Central PMCID: PMC3770579. 3: Vincourt V, Escriou V, Largeau C, Bessodes M, Scherman D, Chaumeil JC, Dumortier G. Altered HepG2 cell models using etomoxir versus tert-butylhydroperoxide. Cell Biol Toxicol. 2011 Oct;27(5):363-70. doi: 10.1007/s10565-011-9193-7. Epub 2011 Jun 26. PubMed PMID: 21706388. 4: Pike LS, Smift AL, Croteau NJ, Ferrick DA, Wu M. Inhibition of fatty acid oxidation by etomoxir impairs NADPH production and increases reactive oxygen species resulting in ATP depletion and cell death in human glioblastoma cells. Biochim Biophys Acta. 2011 Jun;1807(6):726-34. PubMed PMID: 21692241. 5: Abbas HG, Yunus M, Feinendegen LE. Radiochemical synthesis of etomoxir. Appl Radiat Isot. 2011 Feb;69(2):415-7. doi: 10.1016/j.apradiso.2010.10.008. Epub 2010 Oct 19. PubMed PMID: 21036624. 6: Schwarzer M, Faerber G, Rueckauer T, Blum D, Pytel G, Mohr FW, Doenst T. The metabolic modulators, Etomoxir and NVP-LAB121, fail to reverse pressure overload induced heart failure in vivo. Basic Res Cardiol. 2009 Sep;104(5):547-57. doi: 10.1007/s00395-009-0015-5. Epub 2009 Mar 14. PubMed PMID: 19294446. 7: Luiken JJ, Niessen HE, Coort SL, Hoebers N, Coumans WA, Schwenk RW, Bonen A, Glatz JF. Etomoxir-induced partial carnitine palmitoyltransferase-I (CPT-I) inhibition in vivo does not alter cardiac long-chain fatty acid uptake and oxidation rates. Biochem J. 2009 Apr 15;419(2):447-55. doi: 10.1042/BJ20082159. PubMed PMID: 19138173. 8: Hernlund E, Ihrlund LS, Khan O, Ates YO, Linder S, Panaretakis T, Shoshan MC. Potentiation of chemotherapeutic drugs by energy metabolism inhibitors 2-deoxyglucose and etomoxir. Int J Cancer. 2008 Jul 15;123(2):476-83. doi: 10.1002/ijc.23525. PubMed PMID: 18452174. 9: Holubarsch CJ, Rohrbach M, Karrasch M, Boehm E, Polonski L, Ponikowski P, Rhein S. A double-blind randomized multicentre clinical trial to evaluate the efficacy and safety of two doses of etomoxir in comparison with placebo in patients with moderate congestive heart failure: the ERGO (etomoxir for the recovery of glucose oxidation) study. Clin Sci (Lond). 2007 Aug;113(4):205-12. PubMed PMID: 17319797. 10: Högberg H, Engblom L, Ekdahl A, Lidell V, Walum E, Alberts P. Temperature dependence of O2 consumption; opposite effects of leptin and etomoxir on respiratory quotient in mice. Obesity (Silver Spring). 2006 Apr;14(4):673-82. PubMed PMID: 16741269. 11: Caspary F, Elliott G, Navé BT, Verzaal P, Rohrbach M, Das PK, Nagelkerken L, Nieland JD. A new therapeutic approach to treat psoriasis by inhibition of fatty acid oxidation by Etomoxir. Br J Dermatol. 2005 Nov;153(5):937-44. PubMed PMID: 16225603. 12: Horn CC, Ji H, Friedman MI. Etomoxir, a fatty acid oxidation inhibitor, increases food intake and reduces hepatic energy status in rats. Physiol Behav. 2004 Mar;81(1):157-62. PubMed PMID: 15059695. 13: Xu FY, Taylor WA, Hurd JA, Hatch GM. Etomoxir mediates differential metabolic channeling of fatty acid and glycerol precursors into cardiolipin in H9c2 cells. J Lipid Res. 2003 Feb;44(2):415-23. Epub 2002 Nov 4. PubMed PMID: 12576524. 14: Cabrero A, Merlos M, Laguna JC, Carrera MV. Down-regulation of acyl-CoA oxidase gene expression and increased NF-kappaB activity in etomoxir-induced cardiac hypertrophy. J Lipid Res. 2003 Feb;44(2):388-98. Epub 2002 Nov 4. PubMed PMID: 12576521. 15: Schrauwen P, Hinderling V, Hesselink MK, Schaart G, Kornips E, Saris WH, Westerterp-Plantenga M, Langhans W. Etomoxir-induced increase in UCP3 supports a role of uncoupling protein 3 as a mitochondrial fatty acid anion exporter. FASEB J. 2002 Oct;16(12):1688-90. Epub 2002 Aug 21. PubMed PMID: 12206997. 16: Hinderling VB, Schrauwen P, Langhans W, Westerterp-Plantenga MS. The effect of etomoxir on 24-h substrate oxidation and satiety in humans. Am J Clin Nutr. 2002 Jul;76(1):141-7. PubMed PMID: 12081827. 17: Merrill CL, Ni H, Yoon LW, Tirmenstein MA, Narayanan P, Benavides GR, Easton MJ, Creech DR, Hu CX, McFarland DC, Hahn LM, Thomas HC, Morgan KT. Etomoxir-induced oxidative stress in HepG2 cells detected by differential gene expression is confirmed biochemically. Toxicol Sci. 2002 Jul;68(1):93-101. PubMed PMID: 12075114. 18: Kato K, Lukas A, Chapman DC, Rupp H, Dhalla NS. Differential effects of etomoxir treatment on cardiac Na+-K+ ATPase subunits in diabetic rats. Mol Cell Biochem. 2002 Mar;232(1-2):57-62. PubMed PMID: 12030380. 19: Rupp H, Maisch B. [Functional genomics of pressure-loaded cardiomyocytes: etomoxir in heart failure?]. Herz. 2002 Mar;27(2):166-73. Review. German. PubMed PMID: 12025461. 20: Bitar MS. Co-administration of etomoxir and RU-486 mitigates insulin resistance in hepatic and muscular tissues of STZ-induced diabetic rats. Horm Metab Res. 2001 Oct;33(10):577-84. PubMed PMID: 11607876.