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MedKoo Cat#: 564697 | Name: Etomoxir
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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
Etomoxir
CAS#124083-20-1

Theoretical Analysis

MedKoo Cat#: 564697

Name: Etomoxir

CAS#: 124083-20-1

Chemical Formula: C17H23ClO4

Exact Mass: 326.1285

Molecular Weight: 326.82

Elemental Analysis: C, 62.48; H, 7.09; Cl, 10.85; O, 19.58

Price and Availability

Size Price Availability Quantity
5mg USD 265.00 2 Weeks
10mg USD 435.00 2 Weeks
50mg USD 955.00 2 Weeks
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Related CAS #
828934-41-4 (sodium) 82258-36-4 (racemic) 124083-20-1
Synonym
Etomoxir; B 807-54; B807-54; B-807-54; B 80754; B80754; B-80754; (R)-(+)-Etomoxir;
IUPAC/Chemical Name
Ethyl (2R)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate
InChi Key
DZLOHEOHWICNIL-QGZVFWFLSA-N
InChi Code
InChI=1S/C17H23ClO4/c1-2-20-16(19)17(13-22-17)11-5-3-4-6-12-21-15-9-7-14(18)8-10-15/h7-10H,2-6,11-13H2,1H3/t17-/m1/s1
SMILES Code
O=C([C@]1(CCCCCCOC2=CC=C(Cl)C=C2)OC1)OCC
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
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#A24M04B12
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Etomoxir ((R)-(+)-Etomoxir) 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 140.0 428.37
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 326.82 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. 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:
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.
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: Divakaruni AS, Hsieh WY, Minarrieta L, Duong TN, Kim KKO, Desousa BR, Andreyev AY, Bowman CE, Caradonna K, Dranka BP, Ferrick DA, Liesa M, Stiles L, Rogers GW, Braas D, Ciaraldi TP, Wolfgang MJ, Sparwasser T, Berod L, Bensinger SJ, Murphy AN. Etomoxir Inhibits Macrophage Polarization by Disrupting CoA Homeostasis. Cell Metab. 2018 Sep 4;28(3):490-503.e7. doi: 10.1016/j.cmet.2018.06.001. Epub 2018 Jun 28. PMID: 30043752; PMCID: PMC6125190. 2: Raud B, Roy DG, Divakaruni AS, Tarasenko TN, Franke R, Ma EH, Samborska B, Hsieh WY, Wong AH, Stüve P, Arnold-Schrauf C, Guderian M, Lochner M, Rampertaap S, Romito K, Monsale J, Brönstrup M, Bensinger SJ, Murphy AN, McGuire PJ, Jones RG, Sparwasser T, Berod L. Etomoxir Actions on Regulatory and Memory T Cells Are Independent of Cpt1a-Mediated Fatty Acid Oxidation. Cell Metab. 2018 Sep 4;28(3):504-515.e7. doi: 10.1016/j.cmet.2018.06.002. Epub 2018 Jun 28. PMID: 30043753; PMCID: PMC6747686. 3: Schlaepfer IR, Joshi M. CPT1A-mediated Fat Oxidation, Mechanisms, and Therapeutic Potential. Endocrinology. 2020 Feb 1;161(2):bqz046. doi: 10.1210/endocr/bqz046. PMID: 31900483. 4: Hegardt FG, Serra D, Asins G. Influence of etomoxir on the expression of several genes in liver, testis and heart. Gen Pharmacol. 1995 Sep;26(5):897-904. doi: 10.1016/0306-3623(94)00281-q. PMID: 7557264. 5: 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. 6: Jiang N, Xie B, Xiao W, Fan M, Xu S, Duan Y, Hamsafar Y, Evans AC, Huang J, Zhou W, Lin X, Ye N, Wanggou S, Chen W, Jing D, Fragoso RC, Dugger BN, Wilson PF, Coleman MA, Xia S, Li X, Sun LQ, Monjazeb AM, Wang A, Murphy WJ, Kung HJ, Lam KS, Chen HW, Li JJ. Fatty acid oxidation fuels glioblastoma radioresistance with CD47-mediated immune evasion. Nat Commun. 2022 Mar 21;13(1):1511. doi: 10.1038/s41467-022-29137-3. PMID: 35314680; PMCID: PMC8938495. 7: Nomura M, Liu J, Rovira II, Gonzalez-Hurtado E, Lee J, Wolfgang MJ, Finkel T. Fatty acid oxidation in macrophage polarization. Nat Immunol. 2016 Mar;17(3):216-7. doi: 10.1038/ni.3366. PMID: 26882249; PMCID: PMC6033271. 8: Tan Z, Xiao L, Tang M, Bai F, Li J, Li L, Shi F, Li N, Li Y, Du Q, Lu J, Weng X, Yi W, Zhang H, Fan J, Zhou J, Gao Q, Onuchic JN, Bode AM, Luo X, Cao Y. Targeting CPT1A-mediated fatty acid oxidation sensitizes nasopharyngeal carcinoma to radiation therapy. Theranostics. 2018 Mar 22;8(9):2329-2347. doi: 10.7150/thno.21451. PMID: 29721083; PMCID: PMC5928893. 9: Chen L, Vasoya RP, Toke NH, Parthasarathy A, Luo S, Chiles E, Flores J, Gao N, Bonder EM, Su X, Verzi MP. HNF4 Regulates Fatty Acid Oxidation and Is Required for Renewal of Intestinal Stem Cells in Mice. Gastroenterology. 2020 Mar;158(4):985-999.e9. doi: 10.1053/j.gastro.2019.11.031. Epub 2019 Nov 22. PMID: 31759926; PMCID: PMC7062567. 10: 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. 11: Nasci VL, Chuppa S, Griswold L, Goodreau KA, Dash RK, Kriegel AJ. miR-21-5p regulates mitochondrial respiration and lipid content in H9C2 cells. Am J Physiol Heart Circ Physiol. 2019 Mar 1;316(3):H710-H721. doi: 10.1152/ajpheart.00538.2017. Epub 2019 Jan 18. PMID: 30657727; PMCID: PMC6459316. 12: Klein Geltink RI, O'Sullivan D, Corrado M, Bremser A, Buck MD, Buescher JM, Firat E, Zhu X, Niedermann G, Caputa G, Kelly B, Warthorst U, Rensing-Ehl A, Kyle RL, Vandersarren L, Curtis JD, Patterson AE, Lawless S, Grzes K, Qiu J, Sanin DE, Kretz O, Huber TB, Janssens S, Lambrecht BN, Rambold AS, Pearce EJ, Pearce EL. Mitochondrial Priming by CD28. Cell. 2017 Oct 5;171(2):385-397.e11. doi: 10.1016/j.cell.2017.08.018. Epub 2017 Sep 14. PMID: 28919076; PMCID: PMC5637396. 13: Shim JK, Choi S, Yoon SJ, Choi RJ, Park J, Lee EH, Cho HJ, Lee S, Teo WY, Moon JH, Kim HS, Kim EH, Cheong JH, Chang JH, Yook JI, Kang SG. Etomoxir, a carnitine palmitoyltransferase 1 inhibitor, combined with temozolomide reduces stemness and invasiveness in patient-derived glioblastoma tumorspheres. Cancer Cell Int. 2022 Oct 11;22(1):309. doi: 10.1186/s12935-022-02731-7. PMID: 36221088; PMCID: PMC9552483. 14: Raud B, McGuire PJ, Jones RG, Sparwasser T, Berod L. Fatty acid metabolism in CD8+ T cell memory: Challenging current concepts. Immunol Rev. 2018 May;283(1):213-231. doi: 10.1111/imr.12655. PMID: 29664569; PMCID: PMC6691976. 15: Huang L, Nazarova EV, Tan S, Liu Y, Russell DG. Growth of Mycobacterium tuberculosis in vivo segregates with host macrophage metabolism and ontogeny. J Exp Med. 2018 Apr 2;215(4):1135-1152. doi: 10.1084/jem.20172020. Epub 2018 Mar 2. PMID: 29500179; PMCID: PMC5881470. 16: Spurway TD, Pogson CI, Sherratt HS, Agius L. Etomoxir, sodium 2-[6-(4-chlorophenoxy)hexyl] oxirane-2-carboxylate, inhibits triacylglycerol depletion in hepatocytes and lipolysis in adipocytes. FEBS Lett. 1997 Mar 3;404(1):111-4. doi: 10.1016/s0014-5793(97)00103-8. PMID: 9074648. 17: Peng S, Chen D, Cai J, Yuan Z, Huang B, Li Y, Wang H, Luo Q, Kuang Y, Liang W, Liu Z, Wang Q, Cui Y, Wang H, Liu X. Enhancing cancer-associated fibroblast fatty acid catabolism within a metabolically challenging tumor microenvironment drives colon cancer peritoneal metastasis. Mol Oncol. 2021 May;15(5):1391-1411. doi: 10.1002/1878-0261.12917. Epub 2021 Feb 16. PMID: 33528867; PMCID: PMC8096782. 18: Rupp H, Maisch B. Funktionelle Genomik des druckbelasteten Kardiozyten: Etomoxir bei Herzinsuffizienz? [Functional genomics of pressure-loaded cardiomyocytes: etomoxir in heart failure?]. Herz. 2002 Mar;27(2):166-73. German. doi: 10.1007/s00059-002-2357-8. PMID: 12025461. 19: 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. doi: 10.1016/j.physbeh.2004.01.007. PMID: 15059695. 20: Turcani M, Rupp H. Etomoxir improves left ventricular performance of pressure-overloaded rat heart. Circulation. 1997 Nov 18;96(10):3681-6. doi: 10.1161/01.cir.96.10.3681. PMID: 9396471.