2-methyl-2-({[(propan-2-yl)carbamoyl]oxy}methyl)pentyl carbamate

• ChemBase ID: 278
• Molecular Formular: C12H24N2O4
• Molecular Mass: 260.32996
• Monoisotopic Mass: 260.17360726
• SMILES: O(CC(CCC)(COC(=O)N)C)C(=O)NC(C)C
• Canonical SMILES: CCCC(COC(=O)N)(COC(=O)NC(C)C)C
• InChI: InChI=1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)
• InChIKey: OFZCIYFFPZCNJE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-2-({[(propan-2-yl)carbamoyl]oxy}methyl)pentyl carbamate; 2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate
• IUPAC Traditional name: 2-{[(isopropylcarbamoyl)oxy]methyl}-2-methylpentyl carbamate; carisoprodol
• Brand Name: Artifar; Caridolin; Chinchen; Fibrosona; Flexagilt; Flexagit; Flexidon; Listaflex; Meprodat; Muslax; Neotica; Scutamil-C; Skutamil; Soma; Carisoma; Mioartrina; Miolisodal; Mioratrina; Flexartal; Atonalyt; Nospasm; Relasom; Somanil; Apesan; Arusal; Flexal; Mioril; Sanoma
• Synonyms: N-(1-Methylethyl)carbamic Acid 2-[[(Aminocarbonyl)oxy]methyl]-2-methylpentyl Ester; Domarax; N-Isopropyl-2-methyl-2-propyl-1,3-propanediol Dicarbamate; Flexal; NIH 10966; NSC 172124; Somalgit; Stialgin; 2-methyl-2-({[(propan-2-yl)carbamoyl]oxy}methyl)pentyl carbamate; Sanoma; Isoprothane; Isoprotane; Isomeprobamate; Carisoprodatum; Carisoprodate; Carisoprodol; 1-Methylethyl)carbamic acid 2-[[(aminocarbonyl)oxy]-methyl]-2-methylpentyl ester; Carisoprodol

Database IDs

• CAS Number: 78-44-4
• EC Number: 201-118-7
• MDL Number: MFCD00057661
• PubChem SID: 160963741; 24278083; 46506377
• PubChem CID: 2576
• CHEBI ID: 3419
• ATC CODE: M03BA02
• CHEMBL: 1233
• Chemspider ID: 2478
• DrugBank ID: DB00395
• KEGG ID: D00768
• Unique Ingredient Identifier: 21925K482H
• Wikipedia Title: Carisoprodol
• Medline Plus: a682578

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.057489
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.9243119
• LogD (pH = 7.4): 1.9243119
• Log P: 1.9243119
• Molar Refractivity: 67.1008 cm^3
• Polarizability: 26.694498 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.76
• LOG S: -2.52
• Solubility (Water): 7.92e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.3 mg/ml; Chloroform; DMSO; ethanol: soluble
• Apperance: Off-White Low Melting Solid
• Melting Point: 90-94°C
• Hydrophobicity(logP): 2.1; 2.341

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: FB3325000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22-36/37/38
• Safety Statements: 36; S:25-26-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule IV
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Half Life: 2 hours
• Metabolism: Hepatic (CYP2C19-mediated)
• Protein Bound: 60%
• Legal Status: Schedule IV (US)
• Pregnancy Category: C

Product Information

• Purity: 95%
• Salt Data: Free Base

DETAILS

DrugBank - DB00395

• Drug Groups: approved
• Description: A centrally acting skeletal muscle relaxant whose mechanism of action is not completely understood but may be related to its sedative actions. 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, p1202)
• Indication: For the relief of discomfort associated with acute, painful, musculoskeletal conditions.
• Pharmacology: Carisoprodol is used as a skeletal muscle relaxant. One of its metabolites, meprobamate, is available as an anxiolytic agent.
• Toxicity: Symptoms of overdose include drowsiness, giddiness, nausea, indigestion, or rash. Other adverse effects attributed to therapeutic use of carisoprodol include dizziness, irritability, insomnia, diplopia, temporary loss of vision, ataxia, weakness, headache, and dysarthria. Non-CNS adverse effects include gastrointestinal complaints, tachycardia, and postural hypotension. Patients sensitive to sulfites or tartrazine may experience wheezing, allergic rashes including erythema multiforme, or anaphylaxis after using some preparations of carisoprodol which contain such additives
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Metabolized in the liver via the cytochrome P450 oxidase isozyme CYP2C19.
• Half Life: 8 hours
• Protein Binding: 60%
• Elimination: Carisoprodol is eliminated by both renal and non-renal routes.
• Clearance: * oral cl=0.772 L/hour/kg [Women]; * oral cl=0.38 L/hour/kg [Men]
• References: Toth PP, Urtis J: Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67. [Pubmed] ; Chou R, Peterson K, Helfand M: Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75. [Pubmed] ; Littrell RA, Hayes LR, Stillner V: Carisoprodol (Soma): a new and cautious perspective on an old agent. South Med J. 1993 Jul;86(7):753-6. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S2049

Research Area: Neurological Disease
Biological Activity:

Sigma Aldrich - C8759

Biochem/physiol Actions
Metabolite of meprobamate that is a skeletal muscle relaxant, reduces muscle spasm by depression of brainstem neurons.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8759.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C183580

Muscle relaxant (skeletal).

REFERENCES

• Toth PP, Urtis J: Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67. Pubmed
• Littrell RA, Hayes LR, Stillner V: Carisoprodol (Soma): a new and cautious perspective on an old agent. South Med J. 1993 Jul;86(7):753-6. Pubmed
• Chou R, Peterson K, Helfand M: Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75. Pubmed
• Musso, D., et al.: J. Med. Chem. 46, 399 (2003)
• Newman, P., et al.: Eur. J. Clin. Pharm., 23, 31 (1982).