CXA-10 | CAS#875685-46-4 | Nrf2 & NF-κB Modulator

MedKoo Cat#: 527714 | Name: CXA-10

Description:

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

CXA-10, also known as 10-Nitrooleic acid, is an endogenous nitro-fatty acid (NFA) modulator of Nrf2 and NF-κB potentially for the treatment of acute kidney injury and renal failure. CXA-10 upregulated expression of caveolin-1, the major structural component of caveolae. CXA-10 significantly attenuated increases in plasma cholesterol, heart weight, and kidney weight observed in the model without impacting systemic arterial blood pressure. CXA-10 also reduced albuminuria, nephrinuria, glomerular hypertrophy, and glomerulosclerosis in the model, At the appropriate dose, the nitrated fatty acid CXA-10 exhibits anti-inflammatory and antifibrotic effects in the kidney and limits renal injury in a model of CKD.

Chemical Structure

CXA-10

CAS#875685-46-4

Theoretical Analysis

MedKoo Cat#: 527714

Name: CXA-10

CAS#: 875685-46-4

Chemical Formula: C18H33NO4

Exact Mass: 327.2410

Molecular Weight: 327.47

Elemental Analysis: C, 66.02; H, 10.16; N, 4.28; O, 19.54

Price and Availability

Size	Price	Availability
1mg	USD 90.00	Ready to Ship
5mg	USD 350.00	Ready to Ship
10mg	USD 550.00	Ready to Ship
25mg	USD 950.00	Ready to Ship
50mg	USD 1,650.00	Ready to Ship

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Related CAS #

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Synonym

CXA-10; CXA 10; CXA10; 10-Nitrooleic acid; 10-nitro-9(E)-octadec-9-enoic acid;

IUPAC/Chemical Name

(E)-10-nitrooctadec-9-enoic acid

InChi Key

WRADPCFZZWXOTI-BMRADRMJSA-N

InChi Code

InChI=1S/C18H33NO4/c1-2-3-4-5-8-11-14-17(19(22)23)15-12-9-6-7-10-13-16-18(20)21/h15H,2-14,16H2,1H3,(H,20,21)/b17-15+

SMILES Code

CCCCCCCC/C([N+]([O-])=O)=C\CCCCCCCC(O)=O

Appearance

liquid

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 ethanol

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in ethanol

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#Y23X06M30

QC Data

View QC data: current batch, Lot#Y23X06M30

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

CXA-10 is a nitro fatty acid that has potential effects in disease states in which oxidative stress, inflammation, fibrosis, and/or direct tissue toxicity play significant roles.

In vitro activity:

Treatment of keratinocytes with CXA-10 for 6h upregulated mRNA expression of heat shock proteins 27 and 70; primary antioxidants heme oxygenase-1 and catalase; glutathione S-transferase A1/2, GSTA3, and GSTA4; and Cox-2. CXA-10 also upregulated expression of caveolin-1. Reference: Free Radic Biol Med. 2014 Feb;67:1-9. https://pubmed.ncbi.nlm.nih.gov/24140437/

In vivo activity:

To be determined

	Solvent	mg/mL	mM
Solubility
	Ethanol	1.0	3.05

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 327.47 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. Zheng R, Heck DE, Black AT, Gow A, Laskin DL, Laskin JD. Regulation of keratinocyte expression of stress proteins and antioxidants by the electrophilic nitrofatty acids 9- and 10-nitrooleic acid. Free Radic Biol Med. 2014 Feb;67:1-9. doi: 10.1016/j.freeradbiomed.2013.10.011. Epub 2013 Oct 15. PMID: 24140437; PMCID: PMC4391631. 2. Gorczynski MJ, Smitherman PK, Akiyama TE, Wood HB, Berger JP, King SB, Morrow CS. Activation of peroxisome proliferator-activated receptor gamma (PPARgamma) by nitroalkene fatty acids: importance of nitration position and degree of unsaturation. J Med Chem. 2009 Aug 13;52(15):4631-9. doi: 10.1021/jm900326c. PMID: 19719236; PMCID: PMC2741172.

In vitro protocol:

In vivo protocol:

To be determined

1: Arbeeny CM, Ling H, Smith MM, O'Brien S, Wawersik S, Ledbetter SR, McAlexander A, Schopfer FJ, Willette RN, Jorkasky DK. CXA-10, a Nitrated Fatty Acid, Is Renoprotective in Deoxycorticosterone Acetate-Salt Nephropathy. J Pharmacol Exp Ther. 2019 Jun;369(3):503-510. doi: 10.1124/jpet.118.254755. Epub 2019 Mar 20. PMID: 30894457. 2: Garner RM, Mould DR, Chieffo C, Jorkasky DK. Pharmacokinetic and Pharmacodynamic Effects of Oral CXA-10, a Nitro Fatty Acid, After Single and Multiple Ascending Doses in Healthy and Obese Subjects. Clin Transl Sci. 2019 Nov;12(6):667-676. doi: 10.1111/cts.12672. Epub 2019 Aug 12. PMID: 31343124; PMCID: PMC6853153. 3: Medrek S, Melendres-Groves L. Evolving nonvasodilator treatment options for pulmonary arterial hypertension. Curr Opin Pulm Med. 2022 Sep 1;28(5):361-368. doi: 10.1097/MCP.0000000000000887. Epub 2022 Jul 16. PMID: 35838352. 4: Schopfer FJ, Vitturi DA, Jorkasky DK, Freeman BA. Nitro-fatty acids: New drug candidates for chronic inflammatory and fibrotic diseases. Nitric Oxide. 2018 Sep 1;79:31-37. doi: 10.1016/j.niox.2018.06.006. Epub 2018 Jun 23. PMID: 29944935; PMCID: PMC6280193. 5: Perecko T, Hoferova Z, Hofer M, Pereckova J, Falk M. Administration of nitro- oleic acid mitigates radiation-induced hematopoietic injury in mice. Life Sci. 2022 Dec 1;310:121106. doi: 10.1016/j.lfs.2022.121106. Epub 2022 Oct 20. PMID: 36272465. 6: Mollenhauer M, Mehrkens D, Klinke A, Lange M, Remane L, Friedrichs K, Braumann S, Geißen S, Simsekyilmaz S, Nettersheim FS, Lee S, Peinkofer G, Geisler AC, Geis B, Schwoerer AP, Carrier L, Freeman BA, Dewenter M, Luo X, El- Armouche A, Wagner M, Adam M, Baldus S, Rudolph V. Nitro-fatty acids suppress ischemic ventricular arrhythmias by preserving calcium homeostasis. Sci Rep. 2020 Sep 18;10(1):15319. doi: 10.1038/s41598-020-71870-6. PMID: 32948795; PMCID: PMC7501300. 7: Zhou C, Su M, Sun P, Tang X, Yin KJ. Nitro-oleic acid-mediated blood-brain barrier protection reduces ischemic brain injury. Exp Neurol. 2021 Dec;346:113861. doi: 10.1016/j.expneurol.2021.113861. Epub 2021 Sep 7. PMID: 34499902. 8: Nettersheim FS, Lemties J, Braumann S, Geißen S, Bokredenghel S, Nies R, Hof A, Winkels H, Freeman BA, Klinke A, Rudolph V, Baldus S, Mehrkens D, Mollenhauer M, Adam M. Nitro-oleic acid reduces thoracic aortic aneurysm progression in a mouse model of Marfan syndrome. Cardiovasc Res. 2022 Jul 20;118(9):2211-2225. doi: 10.1093/cvr/cvab256. PMID: 34324651. 9: Hernychova L, Alexandri E, Tzakos AG, Zatloukalová M, Primikyri A, Gerothanassis IP, Uhrik L, Šebela M, Kopečný D, Jedinák L, Vacek J. Serum albumin as a primary non-covalent binding protein for nitro-oleic acid. Int J Biol Macromol. 2022 Apr 1;203:116-129. doi: 10.1016/j.ijbiomac.2022.01.050. Epub 2022 Jan 19. PMID: 35063491. 10: Bago Á, Cayuela ML, Gil A, Calvo E, Vázquez J, Queiro A, Schopfer FJ, Radi R, Serrador JM, Íñiguez MA. Nitro-oleic acid regulates T cell activation through post-translational modification of calcineurin. Proc Natl Acad Sci U S A. 2023 Jan 24;120(4):e2208924120. doi: 10.1073/pnas.2208924120. Epub 2023 Jan 18. PMID: 36652486; PMCID: PMC9942794. 11: Manni ML, Heinrich VA, Buchan GJ, O'Brien JP, Uvalle C, Cechova V, Koudelka A, Ukani D, Rawas-Qalaji M, Oury TD, Hart R, Ellgass M, Mullett SJ, Fajt ML, Wenzel SE, Holguin F, Freeman BA, Wendell SG. Nitroalkene fatty acids modulate bile acid metabolism and lung function in obese asthma. Sci Rep. 2021 Sep 7;11(1):17788. doi: 10.1038/s41598-021-96471-9. PMID: 34493738; PMCID: PMC8423735. 12: Braumann S, Schumacher W, Im NG, Nettersheim FS, Mehrkens D, Bokredenghel S, Hof A, Nies RJ, Adler C, Winkels H, Knöll R, Freeman BA, Rudolph V, Klinke A, Adam M, Baldus S, Mollenhauer M, Geißen S. Nitro-Oleic Acid (NO2-OA) Improves Systolic Function in Dilated Cardiomyopathy by Attenuating Myocardial Fibrosis. Int J Mol Sci. 2021 Aug 22;22(16):9052. doi: 10.3390/ijms22169052. PMID: 34445757; PMCID: PMC8396484. 13: Zhao Y, Chang Z, Zhao G, Lu H, Xiong W, Liang W, Wang H, Villacorta L, Garcia-Barrio MT, Zhu T, Guo Y, Fan Y, Chang L, Schopfer FJ, Freeman BA, Zhang J, Chen YE. Suppression of Vascular Macrophage Activation by Nitro-Oleic Acid and its Implication for Abdominal Aortic Aneurysm Therapy. Cardiovasc Drugs Ther. 2021 Oct;35(5):939-951. doi: 10.1007/s10557-020-07031-8. Epub 2020 Jul 15. PMID: 32671602; PMCID: PMC7855321. 14: Tsikas D. Measurement of nitro-oleic acid and nitro-linoleic acid in plasma by GC-MS/MS and LC-MS/MS in health and disease: The significance of the internal standard. J Chromatogr B Analyt Technol Biomed Life Sci. 2023 Apr 15;1221:123684. doi: 10.1016/j.jchromb.2023.123684. Epub 2023 Mar 21. PMID: 36966607. 15: Perecko T, Pereckova J, Hoferova Z, Falk M. Cell-type specific anti- cancerous effects of nitro-oleic acid and its combination with gamma irradiation. Biol Chem. 2023 Sep 15;405(3):177-187. doi: 10.1515/hsz-2023-0150. PMID: 37712609. 16: Pereckova J, Pekarova M, Szamecova N, Hoferova Z, Kamarytova K, Falk M, Perecko T. Nitro-Oleic Acid Inhibits Stemness Maintenance and Enhances Neural Differentiation of Mouse Embryonic Stem Cells via STAT3 Signaling. Int J Mol Sci. 2021 Sep 15;22(18):9981. doi: 10.3390/ijms22189981. PMID: 34576143; PMCID: PMC8468660.