Metaxalone-d6 | CAS#1189944-95-3 | Metaxalone quantification internal standard

MedKoo Cat#: 463925 | Name: Metaxalone-d6

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Description:

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

Metaxalone-d6 is intended for use as an internal standard for the quantification of metaxalone by GC-or LC-MS. Metaxalone is a skeletal muscle relaxant. It inhibits the proliferation of, and induces apoptosis in, RAW 264.7 cells in vitro when used at concentrations ranging from 1 to 100 µM. Metaxalone also reduces LPS-induced increases in COX-1, COX-2, and NF-kB levels and inhibits LPS-induced production of TNF-α, IL-6, and prostaglandin E2 in RAW 264.7 cells. Formulations containing metaxalone have been used in the treatment of lower back pain.

Chemical Structure

Metaxalone-d6

CAS#1189944-95-3

Theoretical Analysis

MedKoo Cat#: 463925

Name: Metaxalone-d6

CAS#: 1189944-95-3

Chemical Formula: C12H9D6NO3

Exact Mass: 227.1429

Molecular Weight: 227.29

Elemental Analysis: C, 63.41; H, 9.31; N, 6.16; O, 21.12

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 485.00	2 Weeks

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Synonym

Metaxalone-d6; Metaxalone d6;

IUPAC/Chemical Name

5-((3,5-bis(methyl-d3)phenoxy)methyl)oxazolidin-2-one

InChi Key

IMWZZHHPURKASS-WFGJKAKNSA-N

InChi Code

InChI=1S/C12H15NO3/c1-8-3-9(2)5-10(4-8)15-7-11-6-13-12(14)16-11/h3-5,11H,6-7H2,1-2H3,(H,13,14)/i1D3,2D3

SMILES Code

[2H]C([2H])(C1=CC(C([2H])([2H])[2H])=CC(OCC(CN2)OC2=O)=C1)[2H]

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Metaxalone-d6 is deuterium labeled Metaxalone.

In vitro activity:

The aim of this study was to investigate whether metaxalone might exert antioxidant and anti-inflammatory effects in HMC3 microglial cells. Control cells and IL-1β-stimulated cells were subsequently treated with metaxalone (10, 20, and 40 µM) for six hours. Metaxalone decreased MAO-A activity and expression, reduced NF-kB, TNF-α, and IL-6, enhanced IL-13, and also increased PPARγ, PGC-1α, and Nrf2 expression. Reference: Int J Mol Sci. 2021 Aug 5;22(16):8425. https://pubmed.ncbi.nlm.nih.gov/34445126/

In vivo activity:

Mouse macrophage RAW264.7 cells were cultured in Dulbecco's Modification of Eagle's Medium containing 10% fetal bovine serum in the presence of metaxalone. Metaxalone (1-100 μM) was found to decrease the number of macrophages by inhibiting the proliferation and stimulating the death of RAW264.7 cells in vitro. Furthermore, levels of caspase-3 were increased by metaxalone or β-caryophyllene and enhanced by their combination. Reference: Curr Mol Med. 2020;20(8):643-652. https://pubmed.ncbi.nlm.nih.gov/32065089/

Preparing Stock Solutions

The following data is based on the product molecular weight 227.29 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. Pallio G, D'Ascola A, Cardia L, Mannino F, Bitto A, Minutoli L, Picciolo G, Squadrito V, Irrera N, Squadrito F, Altavilla D. MAO-A Inhibition by Metaxalone Reverts IL-1β-Induced Inflammatory Phenotype in Microglial Cells. Int J Mol Sci. 2021 Aug 5;22(16):8425. doi: 10.3390/ijms22168425. PMID: 34445126; PMCID: PMC8395141. 2. Yamaguchi M, Levy RM. Metaxalone Suppresses Production of Inflammatory Cytokines Associated with Painful Conditions in Mouse Macrophages RAW264.7 Cells in Vitro: Synergistic Effect with β-caryophyllene. Curr Mol Med. 2020;20(8):643-652. doi: 10.2174/1566524020666200217102508. PMID: 32065089.

In vitro protocol:

Pallio G, D'Ascola A, Cardia L, Mannino F, Bitto A, Minutoli L, Picciolo G, Squadrito V, Irrera N, Squadrito F, Altavilla D. MAO-A Inhibition by Metaxalone Reverts IL-1β-Induced Inflammatory Phenotype in Microglial Cells. Int J Mol Sci. 2021 Aug 5;22(16):8425. doi: 10.3390/ijms22168425. PMID: 34445126; PMCID: PMC8395141.

In vivo protocol:

Yamaguchi M, Levy RM. Metaxalone Suppresses Production of Inflammatory Cytokines Associated with Painful Conditions in Mouse Macrophages RAW264.7 Cells in Vitro: Synergistic Effect with β-caryophyllene. Curr Mol Med. 2020;20(8):643-652. doi: 10.2174/1566524020666200217102508. PMID: 32065089.

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A Randomized, Placebo-Controlled Trial of Ibuprofen Plus Metaxalone, Tizanidine, or Baclofen for Acute Low Back Pain. Ann Emerg Med. 2019 Oct;74(4):512-520. doi: 10.1016/j.annemergmed.2019.02.017. Epub 2019 Apr 5. PMID: 30955985; PMCID: PMC6756993. 5: Vuletić L, Khan MZI, Špoljarić D, Radić M, Cetina-Čižmek B, Filipović-Grčić J. Development of a Clinically Relevant Dissolution Method for Metaxalone Immediate Release Formulations Based on an IVIVC Model. Pharm Res. 2018 Jun 22;35(8):163. doi: 10.1007/s11095-018-2434-1. PMID: 29934663. 6: Moody DE, Fu Y, Fang WB. Inhibition of In Vitro Metabolism of Opioids by Skeletal Muscle Relaxants. Basic Clin Pharmacol Toxicol. 2018 Sep;123(3):327-334. doi: 10.1111/bcpt.12999. Epub 2018 Apr 19. PMID: 29504673. 7: Lin SY. Simultaneous screening and detection of pharmaceutical co-crystals by the one-step DSC-FTIR microspectroscopic technique. Drug Discov Today. 2017 Apr;22(4):718-728. doi: 10.1016/j.drudis.2016.12.001. Epub 2016 Dec 12. PMID: 27979712. 8: Bishop-Freeman SC, Miller A, Hensel EM, Winecker RE. Postmortem Metaxalone (Skelaxin®) Data from North Carolina. J Anal Toxicol. 2015 Oct;39(8):629-36. doi: 10.1093/jat/bkv066. PMID: 26378137. 9: Surmaitis RM, Nappe TM, Cook MD. Serotonin syndrome associated with therapeutic metaxalone in a patient with cirrhosis. Am J Emerg Med. 2016 Feb;34(2):346.e5-6. doi: 10.1016/j.ajem.2015.06.043. Epub 2015 Jun 19. PMID: 26159819. 10: Curtis B, Jenkins C, Wiens AL. A rare fatality attributed solely to metaxalone. J Anal Toxicol. 2015 May;39(4):321-3. doi: 10.1093/jat/bkv008. Epub 2015 Feb 10. PMID: 25673649. 11: Martini DI, Nacca N, Haswell D, Cobb T, Hodgman M. Serotonin syndrome following metaxalone overdose and therapeutic use of a selective serotonin reuptake inhibitor. Clin Toxicol (Phila). 2015 Mar;53(3):185-7. doi: 10.3109/15563650.2015.1009993. Epub 2015 Feb 11. PMID: 25671244. 12: Bosak AR, Skolnik AB. Serotonin syndrome associated with metaxalone overdose. J Med Toxicol. 2014 Dec;10(4):402-5. doi: 10.1007/s13181-014-0404-5. PMID: 24805103; PMCID: PMC4252289. 13: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Metaxalone. 2014 Feb 12. PMID: 31644145. 14: Rao RN, Farah H, Sahu PK, Janarthan M, Naidu ChG. Development and validation of a stability-indicating assay including the isolation and characterization of degradation products of metaxalone by LC-MS. Biomed Chromatogr. 2013 Dec;27(12):1733-40. doi: 10.1002/bmc.2987. Epub 2013 Jul 23. PMID: 23881540. 15: Marothu VK, Dash RN, Vemula S, Donkena S, Devi R, Gorrepati M. Kinetics study of metaxalone degradation under hydrolytic, oxidative and thermal stress conditions using stability-indicating HPLC method. J Pharm Anal. 2012 Dec;2(6):431-436. doi: 10.1016/j.jpha.2012.08.004. Epub 2012 Sep 14. PMID: 29403778; PMCID: PMC5760939. 16: Trivedi RK, Patel MC. Development of a Stability-Indicating RP-UPLC Method for Rapid Determination of Metaxalone and its Degradation Products in Solid Oral Dosage Form. Sci Pharm. 2012 Apr-Jun;80(2):353-66. doi: 10.3797/scipharm.1112-08. Epub 2012 Feb 21. PMID: 22896822; PMCID: PMC3383218. 17: Goswami D, Saha A, Gurule S, Khuroo A, Monif T, Vats P. Metaxalone estimation in biological matrix using high-throughput LC-MS/MS bioanalytical method. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Aug 1;902:132-6. doi: 10.1016/j.jchromb.2012.05.034. Epub 2012 Jun 4. PMID: 22766230. 18: Panda SS, Patanaik D, Ravi Kumar BV. New Stability-Indicating RP-HPLC Method for Determination of Diclofenac Potassium and Metaxalone from their Combined Dosage Form. Sci Pharm. 2012 Jan-Mar;80(1):127-37. doi: 10.3797/scipharm.1109-16. Epub 2011 Dec 5. PMID: 22396909; PMCID: PMC3293350. 19: Richards BL, Whittle SL, Buchbinder R. Muscle relaxants for pain management in rheumatoid arthritis. Cochrane Database Syst Rev. 2012 Jan 18;1:CD008922. doi: 10.1002/14651858.CD008922.pub2. PMID: 22258993. 20: Phillips PJ, Smith SG, Kolpin DW, Zaugg SD, Buxton HT, Furlong ET, Esposito K, Stinson B. Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents. Environ Sci Technol. 2010 Jul 1;44(13):4910-6. doi: 10.1021/es100356f. PMID: 20521847; PMCID: PMC2893609.