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    Chemistry

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    Also known as: 1665-48-1, Skelaxin, Zorane, Methaxalonum, Metaxalon, Methoxolone
    Molecular Formula
    C12H15NO3
    Molecular Weight
    221.25  g/mol
    InChI Key
    IMWZZHHPURKASS-UHFFFAOYSA-N
    FDA UNII
    1NMA9J598Y
    Metaxalone
    Metaxalone is an oxazolidinone with centrally-acting skeletal muscle relaxant properties. Although the exact mechanism through which metaxalone exerts its effect is largely unknown, it might be due to general central nervous system (CNS) depression. Metaxalone has no direct effect on the contractile mechanisms of striated muscle, the motor end plate, or the nerve fiber.
    The physiologic effect of metaxalone is by means of Centrally-mediated Muscle Relaxation.
    1 2D Structure

    Metaxalone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one
    2.1.2 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)
    2.1.3 InChI Key
    IMWZZHHPURKASS-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=CC(=C1)OCC2CNC(=O)O2)C
    2.2 Other Identifiers
    2.2.1 UNII
    1NMA9J598Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ahr 438

    2. Skelaxin

    2.3.2 Depositor-Supplied Synonyms

    1. 1665-48-1

    2. Skelaxin

    3. Zorane

    4. Methaxalonum

    5. Metaxalon

    6. Methoxolone

    7. 5-((3,5-dimethylphenoxy)methyl)oxazolidin-2-one

    8. Metazalone

    9. Metazolone

    10. Metaxolone

    11. Ahr-438

    12. Metaxalonum [latin]

    13. Metassalone [dcit]

    14. 5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one

    15. 2-oxazolidinone, 5-[(3,5-dimethylphenoxy)methyl]-

    16. Ahr 438

    17. Metaxalonum [inn-latin]

    18. Metaxalona [inn-spanish]

    19. Nsc 170959

    20. 5-(3,5-xyloloxymethyl)oxazolidin-2-one

    21. Cl 39,148

    22. Flexura

    23. 5-((3,5-xylyloxy)methyl)-2-oxazolidinone

    24. 5-[(3,5-xylyloxy)methyl]-2-oxazolidinone

    25. 2-oxazolidinone, 5-((3,5-xylyloxy)methyl)-

    26. 5-((3,5-dimethylphenoxy)methyl)-2-oxazolidinone

    27. Mfcd00867700

    28. Nsc170959

    29. 5-[(3,5-dimethylphenoxy)methyl]oxazolidin-2-one

    30. Nsc-170959

    31. 2-oxazolidinone, 5-((3,5-dimethylphenoxy)methyl)-

    32. 5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one

    33. Mls003106749

    34. 1nma9j598y

    35. Chebi:6797

    36. 5-[(3,5-dimethylphenoxy)methyl]-2-oxazolidinone

    37. Ncgc00095116-01

    38. Dsstox_cid_3269

    39. 2-oxazolidinone, 5-[(3,5-xylyloxy)methyl]-

    40. Dsstox_rid_76949

    41. Dsstox_gsid_23269

    42. Metaxalona [spanish]

    43. Metassalone

    44. Metaxalona

    45. Metaxalonum

    46. Cas-1665-48-1

    47. Metaxalone [usan:inn:ban]

    48. Hsdb 3236

    49. Sr-05000001978

    50. Einecs 216-777-6

    51. 5-((3,5-dimethylphenoxy)methyl)-1,3-oxazolidin-2-one

    52. Brn 0884592

    53. Unii-1nma9j598y

    54. .meta.xalone

    55. .meta.zalone

    56. .meta.zolone

    57. .meta.xalon

    58. Metaxalone Solution

    59. Skelaxin (tn)

    60. Spectrum_001741

    61. Metaxalone [mi]

    62. Specplus_000656

    63. Metaxalone (usp/inn)

    64. Metaxalone [inn]

    65. Spectrum2_000548

    66. Spectrum3_001666

    67. Spectrum4_000612

    68. Spectrum5_001685

    69. Metaxalone [hsdb]

    70. Metaxalone [usan]

    71. Metaxalone [vandf]

    72. 5-(3,5-dimethylphenoxymethyl)-2-oxazolidinone

    73. Metaxalone [mart.]

    74. Metaxalone [usp-rs]

    75. Metaxalone [who-dd]

    76. Oprea1_438855

    77. Schembl34908

    78. Bspbio_003451

    79. Kbiogr_001164

    80. Kbioss_002221

    81. Divk1c_006752

    82. Spectrum1504229

    83. Spbio_000595

    84. Ahr438

    85. Gtpl7609

    86. Chembl1079604

    87. Dtxsid3023269

    88. Metaxalone [orange Book]

    89. Metaxalone, >=98% (hplc)

    90. Kbio1_001696

    91. Kbio2_002221

    92. Kbio2_004789

    93. Kbio2_007357

    94. Kbio3_002671

    95. Hms1922h07

    96. Hms2093c22

    97. Metaxalone [usp Monograph]

    98. Pharmakon1600-01504229

    99. Bcp28377

    100. Hy-b0678

    101. Tox21_111428

    102. Wln: T5mvotj D1or C1 E1

    103. 2-oxazolidinone,5-xylyloxy)methyl]-

    104. Ccg-39592

    105. Nsc758703

    106. S3730

    107. Stl450994

    108. Stl451511

    109. Akos009035315

    110. Tox21_111428_1

    111. Db00660

    112. Fs-3218

    113. Nsc-758703

    114. Ncgc00095116-02

    115. Ncgc00095116-03

    116. Ncgc00095116-05

    117. Smr001821638

    118. Sy052772

    119. Sbi-0052859.p002

    120. 2-oxazolidinone,5-dimethylphenoxy)methyl]-

    121. Db-043656

    122. Am20060525

    123. Ft-0603568

    124. M2578

    125. 5-(3,5-dimethylphenoxy)methyl-2-oxazolidinone

    126. C07934

    127. D00773

    128. Ab00053284_04

    129. 665m481

    130. A810747

    131. J-010295

    132. Q6823309

    133. Sr-05000001978-1

    134. Sr-05000001978-3

    135. Brd-a94709349-001-02-6

    136. Brd-a94709349-001-03-4

    137. 5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one #

    138. 5-{[(3,5-dimethylphenyl)oxy]methyl}-1,3-oxazolidin-2-one

    139. 5-[(3,5-dimethylphenoxy)methyl]-4,5-dihydro-1,3-oxazol-2-ol

    140. Metaxalone, United States Pharmacopeia (usp) Reference Standard

    141. Metaxalone Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 221.25 g/mol
    Molecular Formula C12H15NO3
    XLogP32.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass221.10519334 g/mol
    Monoisotopic Mass221.10519334 g/mol
    Topological Polar Surface Area47.6 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity247
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameMetaxalone
    PubMed HealthMetaxalone (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelDESCRIPTION Metaxalone tablets are available as an 800 mg oval, convex pink tablet.Chemically, metaxalone is 5-[(3,5- dimethylphenoxy) methyl]-2-oxazolidinone. The empirical formula is C12H15NO3, which corresponds to a molecular weight of 221.25. The...
    Active IngredientMetaxalone
    Dosage FormTablet
    Routeoral; Oral
    Strength400mg; 800mg
    Market StatusTentative Approval; Prescription
    CompanyCorepharma; Amneal Pharms; Sandoz

    2 of 4  
    Drug NameSkelaxin
    PubMed HealthMetaxalone (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelSKELAXIN (metaxalone) is available as an 800 mg oval, scored pink tablet.Chemically, metaxalone is 5-[(3,5- dimethylphenoxy) methyl]-2-oxazolidinone. The empirical formula is C12H15NO3, which corresponds to a molecular weight of 221.25. The structu...
    Active IngredientMetaxalone
    Dosage FormTablet
    RouteOral
    Strength800mg
    Market StatusPrescription
    CompanyKing Pharms

    3 of 4  
    Drug NameMetaxalone
    PubMed HealthMetaxalone (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelDESCRIPTION Metaxalone tablets are available as an 800 mg oval, convex pink tablet.Chemically, metaxalone is 5-[(3,5- dimethylphenoxy) methyl]-2-oxazolidinone. The empirical formula is C12H15NO3, which corresponds to a molecular weight of 221.25. The...
    Active IngredientMetaxalone
    Dosage FormTablet
    Routeoral; Oral
    Strength400mg; 800mg
    Market StatusTentative Approval; Prescription
    CompanyCorepharma; Amneal Pharms; Sandoz

    4 of 4  
    Drug NameSkelaxin
    PubMed HealthMetaxalone (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelSKELAXIN (metaxalone) is available as an 800 mg oval, scored pink tablet.Chemically, metaxalone is 5-[(3,5- dimethylphenoxy) methyl]-2-oxazolidinone. The empirical formula is C12H15NO3, which corresponds to a molecular weight of 221.25. The structu...
    Active IngredientMetaxalone
    Dosage FormTablet
    RouteOral
    Strength800mg
    Market StatusPrescription
    CompanyKing Pharms

    4.2 Therapeutic Uses

    Metaxalone is used as an adjunct to rest, physical therapy, analgesics, and other measures for the relief of discomfort associated with acute, painful musculoskeletal conditions. /Included in US product label/

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 1394

    4.3 Drug Warning

    The most frequent adverse effects of metaxalone are drowsiness, dizziness, headache, nervousness or irritability, nausea, vomiting, and GI upset. Other adverse effects include confusion, anorexia, dry mouth, and urinary retention. Exacerbation of tonic-clonic (grand mal) seizures has also been reported.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 1394

    Hypersensitivity reactions and rash (with or without pruritus) have occurred in patients receiving metaxalone. Anaphylactoid reactions, leukopenia, hemolytic anemia, and jaundice have occurred rarely. Abnormalities in liver function tests, such as increased serum concentrations of AST (SGOT), ALT (SGPT), alkaline phosphatase, and bilirubin, and increased sulfobromophthalein (BSP) retention and thymol turbidity, have occurred in patients receiving metaxalone. Although a causal relationship to metaxalone has not been established, nephrotoxicity and proteinuria have occurred rarely during treatment with the drug; pyuria and nephrolithiasis have also been reported.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 1394

    Safety and efficacy of metaxalone in children 12 years of age or younger have not been established; therefore, the drug should not be administered to children in this age group.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 1394

    Patients should be warned that metaxalone may impair ability to perform hazardous activities requiring mental alertness or physical coordination, such as operating machinery or driving a motor vehicle. In addition, patients should be warned that additive CNS depression may occur when the drug is administered concomitantly with other CNS depressants, including alcohol. Metaxalone should be used with caution in geriatric patients and in patients with hepatic or renal impairment. Liver function studies should be performed periodically during metaxalone therapy in patients with preexisting liver damage. The drug is contraindicated in patients with substantially impaired hepatic or renal function, known hypersensitivity to the drug or any ingredient in the formulation, or a history of drug-induced, hemolytic, or other anemias.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 1394

    For more Drug Warnings (Complete) data for METAXALONE (8 total), please visit the HSDB record page.

    4.4 Drug Indication

    For the treatment of painful peripheral musculoskeletal conditions and spasticity from upper motor neuron syndromes.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 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.

    5.2 MeSH Pharmacological Classification

    Neuromuscular Agents

    Drugs used for their actions on skeletal muscle. Included are agents that act directly on skeletal muscle, those that alter neuromuscular transmission (NEUROMUSCULAR BLOCKING AGENTS), and drugs that act centrally as skeletal muscle relaxants (MUSCLE RELAXANTS, CENTRAL). Drugs used in the treatment of movement disorders are ANTI-DYSKINESIA AGENTS. (See all compounds classified as Neuromuscular Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    METAXALONE
    5.3.2 FDA UNII
    1NMA9J598Y
    5.3.3 Pharmacological Classes
    Centrally-mediated Muscle Relaxation [PE]
    5.4 Absorption, Distribution and Excretion

    Absorption

    The absolute bioavailability of metaxalone from Skelaxin tablets is not known.

    Route of Elimination

    Metaxalone is metabolized by the liver and excreted in the urine as unidentified metabolites.

    Volume of Distribution

    800 L

    Clearance

    68 +/- 50 L/h [Subjects received 1400mg tablet under fasted conditions]

    66 +/- 51 L/h [Subjects received 2400 mg tablets under fasted conditions]

    Although plasma protein binding and absolute bioavailability of metaxalone are not known, the apparent volume of distribution (V/F ~ 800 L) and lipophilicity (log P = 2.42) of metaxalone suggest that the drug is extensively distributed in the tissues. Metaxalone is metabolized by the liver and excreted in the urine as unidentified metabolites.

    US Natl Inst Health; DailyMed. Current Medication Information for Skelaxin (metaxalone) tablet (June 2007). Available from, as of October 15, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=4505

    Peak plasma concentrations of metaxalone occur approximately 3 hours after a 400 mg oral dose under fasted conditions. Thereafter, metaxalone concentrations decline log-linearly with a terminal half-life of 9.0 + or - 4.8 hours. Doubling the dose of skelaxin from 400 mg to 800 mg results in a roughly proportional increase in metaxalone exposure as indicated by peak plasma concentrations (Cmax) and area under the curve (AUC). Dose proportionality at doses above 800 mg has not been studied. The absolute bioavailability of metaxalone is not known

    US Natl Inst Health; DailyMed. Current Medication Information for Skelaxin (metaxalone) tablet (June 2007). Available from, as of October 15, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=4505

    5.5 Metabolism/Metabolites

    Probably hepatic.

    Biotransformations...studied in dogs and in man. 5-(3-methyl-5-carboxyphenoxymethyl)-2-oxazolidinone, major metabolite, is excreted in urine and feces; this also occurs in urine as ester glucuronide. Fission of ether linkage...affords...3,5-xylenol and 5-hydroxymethyloxazolidinone. Oxazolidinone ring is stable in mammals.

    The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 175

    Yields 5-(5-carboxy-3-methylphenoxymethyl)-2-oxazolidone in man & in dogs, yields 3,5-dimethylphenol in man and in dogs. /From table/

    Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. D-93

    Metaxalone is metabolized by the liver and excreted in the urine as unidentified metabolites.

    US Natl Inst Health; DailyMed. Current Medication Information for Skelaxin (metaxalone) tablet (June 2007). Available from, as of October 15, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=4505

    5.6 Biological Half-Life

    9.2 (+/- 4.8) hours

    Terminal half-life /is/ 9.0 + or - 4.8 hours

    US Natl Inst Health; DailyMed. Current Medication Information for Skelaxin (metaxalone) tablet (June 2007). Available from, as of October 15, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=4505

    5.7 Mechanism of Action

    The mechanism of action of metaxalone in humans has not been established, but may be due to general central nervous system depression.

    Metaxalone is a CNS depressant that has sedative and skeletal muscle relaxant effects. The precise mechanism of action of the drug is not known. The skeletal muscle relaxant effects of orally administered metaxalone are minimal and are probably related to its sedative effect. The drug does not directly relax skeletal muscle and, unlike neuromuscular blocking agents, does not depress neuronal conduction, neuromuscular transmission, or muscle excitability.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 1395

    The mechanism of action of metaxalone in humans has not been established, but may be due to general central nervous system depression. Metaxalone has no direct action on the contractile mechanism of striated muscle, the motor end plate or the nerve fiber.

    US Natl Inst Health; DailyMed. Current Medication Information for Skelaxin (metaxalone) tablet (June 2007). Available from, as of October 15, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=4505

    API Reference Price

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PHARMACEUTICALS","customerCountry":"INDIA","quantity":"100.00","actualQuantity":"100","unit":"KGS","unitRateFc":"185","totalValueFC":"18703.3","currency":"USD","unitRateINR":"15715.8","date":"26-Oct-2024","totalValueINR":"1571575","totalValueInUsd":"18703.3","indian_port":"Ahmedabad Air","hs_no":"29349990","bill_no":"6359406","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"ANCONA","supplierAddress":"VIALE AMELIA, 70 00181 ROMA SDNF IT","customerAddress":"882\/1-871, NEAR KANKAVATI ,VILLAGE-"}]
    04-Jan-2021
    26-Oct-2024
    KGS
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    Average Price (USD/KGS)

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    DOSAGE - TABLET;ORAL - 400MG **Federal Regist...DOSAGE - TABLET;ORAL - 400MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 13217

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    DOSAGE - TABLET;ORAL - 800MG **Federal Regist...DOSAGE - TABLET;ORAL - 800MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 13217

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