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

• ChemBase编号: 542
• 分子式: C12H15NO3
• 平均质量: 221.2524
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one; 5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one
• IUPAC传统名: @metaxalone; metaxalone
• 商标名: Skelaxin; Zorane
• 别名: 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

登记号

• CAS号: 1665-48-1
• MDL号: MFCD00867700
• PubChem SID: 46506253; 160964005
• PubChem CID: 15459
• CHEMBL: 1079604
• Chemspider ID: 14709
• DrugBank ID: DB00660
• KEGG ID: D00773
• 美国药典/FDA物质标识码: 1NMA9J598Y
• 维基百科标题: Metaxalone
• Medline Plus: a682010

理论计算性质

JChem

• Acid pKa: 13.1439085
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 2.3718133
• LogD (pH = 7.4): 2.3718126
• Log P: 2.3718133
• 摩尔折射率: 59.322 cm^3
• 极化性: 23.08755 Å^3
• 极化表面积: 47.56 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.63
• LOG S: -2.24
• 溶解度: 1.28e+00 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 121-123°C
• 疏水性(logP): 2.145; 2.3

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 给药途径: Oral
• 生物利用度: Unknown
• 排泄: Renal
• 半衰期: 9.2 (± 4.8) hours
• 代谢: Hepatic
• 法定药品分级: Rx-only (US)
• 妊娠期药物分类: C (US)

产品相关信息

• 纯度: 95%; 95+%; 98%

详细说明

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.

参考文献

• 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