Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H15NO3 |
Molecular Weight | 221.2524 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(OCC2CNC(=O)O2)=CC(C)=C1
InChI
InChIKey=IMWZZHHPURKASS-UHFFFAOYSA-N
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)
Molecular Formula | C12H15NO3 |
Molecular Weight | 221.2524 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including:
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=da237968-1c52-47c3-986b-4f878bd6b173
http://www.drugbank.ca/drugs/DB00660
https://en.wikipedia.org/wiki/Metaxalone
Curator's Comment: description was created based on several sources, including:
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=da237968-1c52-47c3-986b-4f878bd6b173
http://www.drugbank.ca/drugs/DB00660
https://en.wikipedia.org/wiki/Metaxalone
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. 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. Skelaxin is available in an 800 mg scored tablet. Metaxalone relatively low incidence of side effects. The most common adverse reactions to Metaxalone tablets include drowsiness, dizziness, headache, and nervousness or “irritability”, nausea, vomiting, gastrointestinal upset.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4103716/
Curator's Comment: CNS depressant used for acute musculoskeletal spasmodic pain.
Originator
Sources: http://www.patentdocs.org/2010/08/king-pharmaceuticals-inc-v-eon-labs-inc-fed-cir-2010.html
Curator's Comment: Metaxalone was first discovered in the 1960s, and had been sold under the brand name Skelaxin since 1962 -- first by A.H. Robins Co., then by Elan Pharma, Inc ('Elan'), and finally by King.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: central nervous system |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | METAXALONE Approved Useare indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomforts associated with acute, painful musculoskeletal conditions Launch Date-2.20320006E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1816 ng/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
983 ng/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1816 ng/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3510 ng/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15044 ng × h/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7479 ng × h/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
15045 ng × h/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
20833 ng × h/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8 h |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9 h |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
METAXALONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
800 mg 4 times / day multiple, oral Dose: 800 mg, 4 times / day Route: oral Route: multiple Dose: 800 mg, 4 times / day Co-administed with:: Serotonergic drugs Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Serotonin syndrome... AEs leading to discontinuation/dose reduction: Serotonin syndrome Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Serotonin syndrome | Disc. AE | 800 mg 4 times / day multiple, oral Dose: 800 mg, 4 times / day Route: oral Route: multiple Dose: 800 mg, 4 times / day Co-administed with:: Serotonergic drugs Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 7.0 |
no | |||
Page: 3.0 |
weak | |||
Page: 3.0 |
weak | |||
Page: 3.0 |
weak | |||
Page: 3.0 |
yes | |||
Page: 3.0 |
yes | |||
Page: 3.0 |
yes | |||
Page: 3.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Polydrug fatality involving metaxalone. | 2003 Mar |
|
Auditory hallucinations elicited by combined meclizine and metaxalone use at bedtime. | 2004 Nov |
|
Quantification of metaxalone in human plasma by liquid chromatography coupled to tandem mass spectrometry. | 2006 May |
|
High throughput LC-MS/MS method for simultaneous quantification of lamivudine, stavudine and nevirapine in human plasma. | 2007 Jun 15 |
|
Synthesis of poly(ethylene glycol)-metaxalone conjugates and study of its controlled release in vitro. | 2007 Mar 6 |
|
Steady state bioequivalence of generic and innovator formulations of stavudine, lamivudine, and nevirapine in HIV-infected Ugandan adults. | 2008 |
|
Choosing a skeletal muscle relaxant. | 2008 Aug 1 |
|
HPLC-ESI-MS/MS validated method for simultaneous quantification of zopiclone and its metabolites, N-desmethyl zopiclone and zopiclone-N-oxide in human plasma. | 2008 Mar 15 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
Pediatric metaxalone ingestions reported to Texas poison control centers, 2000-2007. | 2010 Jan |
|
Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents. | 2010 Jul 1 |
Patents
Substance Class |
Chemical
Created
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Fri Dec 15 17:17:02 UTC 2023
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Record UNII |
1NMA9J598Y
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Record Status |
Validated (UNII)
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NDF-RT |
N0000175730
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LIVERTOX |
NBK548838
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NDF-RT |
N0000175737
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NCI_THESAURUS |
C29696
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216-777-6
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SUB08817MIG
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15459
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1722
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METAXALONE
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DTXSID3023269
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m322
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3236
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105801-80-7
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1NMA9J598Y
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1665-48-1
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7609
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1396149
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1NMA9J598Y
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C011301
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1027
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CHEMBL1079604
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170959
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59078
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DB00660
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100000081199
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C47606
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MINOR
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MINOR
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |