5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one

• ChemBase ID: 542
• Molecular Formular: C12H15NO3
• Molecular Mass: 221.2524
• Monoisotopic Mass: 221.10519335
• SMILES: O1C(CNC1=O)COc1cc(cc(c1)C)C
• Canonical SMILES: O=C1NCC(O1)COc1cc(C)cc(c1)C
• InChI: 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)
• InChIKey: IMWZZHHPURKASS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one; 5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one
• IUPAC Traditional name: @metaxalone; metaxalone
• Brand Name: Skelaxin; Zorane
• Synonyms: Metassalone [Dcit]; Metaxalon; Metaxalona [INN-Spanish]; Metaxalonum [INN-Latin]; Metaxalonum [Latin]; Methaxalonum; Methoxolone; Metazalone; Metazolone; Metaxalone; 5-((3,5-Dimethylphenoxy)methyl)oxazolidin-2-one; 5-[(3,5-Dimethylphenoxy)methyl]oxazolidin-2-one; AHR-438; Skelaxin; 5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one

Database IDs

• CAS Number: 1665-48-1
• MDL Number: MFCD00867700
• PubChem SID: 46506253; 160964005
• PubChem CID: 15459
• CHEMBL: 1079604
• Chemspider ID: 14709
• DrugBank ID: DB00660
• KEGG ID: D00773
• Unique Ingredient Identifier: 1NMA9J598Y
• Wikipedia Title: Metaxalone
• Medline Plus: a682010

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.1439085
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.3718133
• LogD (pH = 7.4): 2.3718126
• Log P: 2.3718133
• Molar Refractivity: 59.322 cm^3
• Polarizability: 23.08755 Å^3
• Polar Surface Area: 47.56 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.63
• LOG S: -2.24
• Solubility (Water): 1.28e+00 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 121-123°C
• Hydrophobicity(logP): 2.145; 2.3

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: Unknown
• Excretion: Renal
• Half Life: 9.2 (± 4.8) hours
• Metabolism: Hepatic
• Legal Status: Rx-only (US)
• Pregnancy Category: C (US)

Product Information

• Purity: 95%; 95+%; 98%

DETAILS

DrugBank - DB00660

• Drug Groups: approved
• Description: Metaxalone (marketed by King Pharmaceuticals under the brand name Skelaxin?) is a muscle relaxant used to relax muscles and relieve pain caused by strains, sprains, and other musculoskeletal conditions. Its exact mechanism of action is not known, but it may be due to general central nervous system depression. It is considered to be a moderately strong muscle relaxant, with relatively low incidence of side effects. Skelaxin comes in an 800 mg scored tablet. It previously came in both 400 mg and 800 mg tablets. The 400 mg tablet has been discontinued. Possible side effects include nausea, vomiting, drowsiness and CNS side effects such as dizziness, headache, and irritability.
• Indication: For the treatment of painful peripheral musculoskeletal conditions and spasticity from upper motor neuron syndromes.
• Pharmacology: Metaxalone is a skeletal muscle relaxant indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomforts associated with acute, painful musculoskeletal conditions. The mode of action of this drug has not been clearly identified, but may be related to its sedative properties. Metaxalone does not directly relax tense skeletal muscles in man.
• Toxicity: LD₅₀=775mg/kg (Rat, oral); LD₅₀=1690 mg/kg (Mouse, oral). When determining the LD₅₀ in rats and mice, progressive sedation, hypnosis and finally respiratoryfailure were noted as the dosage increased. In dogs, no LD₅₀ could be determined as the higher doses produced an emetic action in 15 to 30 minutes.
• Affected Organisms: Humans and other mammals
• Biotransformation: Probably hepatic.
• Absorption: The absolute bioavailability of metaxalone from Skelaxin tablets is not known.
• Half Life: 9.2 (+/- 4.8) hours
• Elimination: Metaxalone is metabolized by the liver and excreted in the urine as unidentified metabolites.
• Distribution: * 800 L
• Clearance: * 68 +/- 50 L/h [Subjects received 1×400mg tablet under fasted conditions]; * 66 +/- 51 L/h [Subjects received 2×400 mg tablets under fasted conditions]
• References: See S, Ginzburg R: Choosing a skeletal muscle relaxant. Am Fam Physician. 2008 Aug 1;78(3):365-70. [Pubmed] ; Elenbaas JK: Centrally acting oral skeletal muscle relaxants. Am J Hosp Pharm. 1980 Oct;37(10):1313-23. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - M225850

It is a muscle relaxant used to relax muscles and relieve pain.

REFERENCES

• See S, Ginzburg R: Choosing a skeletal muscle relaxant. Am Fam Physician. 2008 Aug 1;78(3):365-70. Pubmed
• Elenbaas JK: Centrally acting oral skeletal muscle relaxants. Am J Hosp Pharm. 1980 Oct;37(10):1313-23. Pubmed