2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate

• ChemBase ID: 306
• Molecular Formular: C11H15NO5
• Molecular Mass: 241.2405
• Monoisotopic Mass: 241.09502259
• SMILES: O(CC(O)COC(=O)N)c1c(OC)cccc1
• Canonical SMILES: COc1ccccc1OCC(COC(=O)N)O
• InChI: InChI=1S/C11H15NO5/c1-15-9-4-2-3-5-10(9)16-6-8(13)7-17-11(12)14/h2-5,8,13H,6-7H2,1H3,(H2,12,14)
• InChIKey: GNXFOGHNGIVQEH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate
• IUPAC Traditional name: methocarbamol
• Brand Name: AHR 85; Avetil; Delaxin; Etroflex; Forbaxin; Glycerylguaiacolate carbamate; Glycerylguajacol-Carbamat; Guaiacol glyceryl ether carbamate; Guaiphenesin carbamate; Guaiphenesine carbamate; Lumirelax; Methocal; Metocarbamol; Metocarbamolo; Metofenia; Metofenina; Miolaxene; Miorilas; Miowas; Myolaxene; Neuraxin; Parabaxin; Perilax; Reflexyn; Relestrid; Robamol; Robaxan; Robaxin; Robaxine; Robaxon; Robinax; Romethocarb; Surquetil; Traumacut; Tresortil
• Synonyms: Methocarbamol; 3-(2-Methoxyphenoxy)-1,2-propanediol 1-Carbamate; 3-(o-Methoxyphenoxy)-2-hydroxypropyl Carbamate; AHR 85; Avetil; Delaxin; Etroflex; Lumirelax; Miolaxene; Neuraxin; Relestrid; Robinax; Guaiacol Glyceryl Ether Carbamate; Guaiacol glyceryl ether carbamate; Robaxin; Methocarbamo; 2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate; 甲氧卡巴莫; 美索巴莫

Database IDs

• CAS Number: 532-03-6
• EC Number: 208-524-3
• MDL Number: MFCD00057662
• PubChem SID: 160963769; 24895283; 46507761
• PubChem CID: 4107
• ATC CODE: M03BA03
• CHEMBL: 1201117
• Chemspider ID: 3964
• DrugBank ID: DB00423
• KEGG ID: D00402
• Unique Ingredient Identifier: 125OD7737X
• Wikipedia Title: Methocarbamol
• Medline Plus: a682579

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.595918
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.44504622
• LogD (pH = 7.4): 0.44504598
• Log P: 0.44504622
• Molar Refractivity: 59.0674 cm^3
• Polarizability: 23.495787 Å^3
• Polar Surface Area: 91.01 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.63
• LOG S: -1.76
• Solubility (Water): 4.21e+00 g/l

PROPERTIES

Physical Property

• Solubility: 7200 mg/L; DMSO; Methanol; Water (sparingly)
• Apperance: White Solid
• Melting Point: 95-97°C
• Hydrophobicity(logP): 0.1; 0.146

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: TY8750000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-42/43
• Safety Statements: 36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Half Life: 1.14–1.24 hours
• Metabolism: Hepatic
• Legal Status: OTC(Canada); Rx-only (US)
• Pregnancy Category: x
• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: 95%
• Salt Data: Free Base

DETAILS

DrugBank - DB00423

• Drug Groups: approved
• Description: A centrally acting muscle relaxant whose mode of action has not been established. It is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1206)
• Indication: For use as an adjunct to rest, physical therapy, and other measures for the relief of discomforts associated with acute, painful musculoskeletal conditions.
• Pharmacology: Methocarbamol is a central muscle relaxant for skeletal muscles, used to treat spasms. It is structurally related to guaifenesin. Methocarbamol's exact mechanism of causing skeletal muscle relaxation is unknown. It is thought to work centrally, perhaps by general depressant effects. It has no direct relaxant effects on striated muscle, nerve fibers, or the motor endplate. It will not directly relax contracted skeletal muscles. The drug has a secondary sedative effect.
• Toxicity: Symptoms of overdose include blurred vision, coma, drowsiness, low blood pressure, nausea, and seizures.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapid. Onset of action is about 30 minutes after oral administration.
• Half Life: 1.14-1.24 hours
• Elimination: Small amounts of unchanged methocarbamol also are excreted in the urine.
• Clearance: * 0.2 – 0.8 L/h/kg [healthy]
• References: Sica DA, Comstock TJ, Davis J, Manning L, Powell R, Melikian A, Wright G: Pharmacokinetics and protein binding of methocarbamol in renal insufficiency and normals. Eur J Clin Pharmacol. 1990;39(2):193-4. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1736

Research Area: Neurological Disease
Biological Activity:
Methocarbamol(Robaxin) is a central muscle relaxant used to treat skeletal muscle spasms. It is the carbamate of guaifenesin, but does not produce guaifenesin as a metabolite, since the carbamate bond is not hydrolyzed metabolically; metabolism is by Phase I ring hydroxylation and O-demethylation, followed by Phase II conjugation. All of the major metabolites are unhydrolyzed carbamates infarction. [1]

Toronto Research Chemicals - M225950

A muscle relaxant (skeletal).

REFERENCES

• Sica DA, Comstock TJ, Davis J, Manning L, Powell R, Melikian A, Wright G: Pharmacokinetics and protein binding of methocarbamol in renal insufficiency and normals. Eur J Clin Pharmacol. 1990;39(2):193-4. Pubmed
• http://en.wikipedia.org/wiki/Methocarbamol
• Topliss, J., et al.: J. Med. Chem., 22, 1238 (1979)
• Walters, W., et al.: Drug Discov. Today., 3, 160 (1979)
• Baldi, P., et al.: Bioinformatics, 16, 412 (1979)
• Kouznetsov, V., et al.: J. Arch. Pharm., 337, 127 (1979)