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1665-48-1 molecular structure
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5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one

ChemBase ID: 542
Molecular Formular: C12H15NO3
Molecular Mass: 221.2524
Monoisotopic Mass: 221.10519335
SMILES and InChIs

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

Cite this record

CBID:542 http://www.chembase.cn/molecule-542.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
1665-48-1
MDL Number
MFCD00867700
PubChem SID
160964005
46506253
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.1439085  H Acceptors
H Donor LogD (pH = 5.5) 2.3718133 
LogD (pH = 7.4) 2.3718126  Log P 2.3718133 
Molar Refractivity 59.322 cm3 Polarizability 23.08755 Å3
Polar Surface Area 47.56 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.63  LOG S -2.24 
Solubility (Water) 1.28e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
121-123°C expand Show data source
Hydrophobicity(logP)
2.145 expand Show data source
2.3 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
TSCA Listed
false expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
Unknown expand Show data source
Excretion
Renal expand Show data source
Half Life
9.2 (± 4.8) hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
C (US) expand Show data source
Purity
95% expand Show data source
95+% expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00660 external link
Item Information
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 external link
It is a muscle relaxant used to relax muscles and relieve pain.

REFERENCES

REFERENCES

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  • • 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
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PATENTS

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