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78-44-4 molecular structure
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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 and InChIs

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

Cite this record

CBID:278 http://www.chembase.cn/molecule-278.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
78-44-4
EC Number
201-118-7
MDL Number
MFCD00057661
PubChem SID
24278083
160963741
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 15.057489  H Acceptors
H Donor LogD (pH = 5.5) 1.9243119 
LogD (pH = 7.4) 1.9243119  Log P 1.9243119 
Molar Refractivity 67.1008 cm3 Polarizability 26.694498 Å3
Polar Surface Area 90.65 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.76  LOG S -2.52 
Solubility (Water) 7.92e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.3 mg/ml expand Show data source
Chloroform expand Show data source
DMSO expand Show data source
ethanol: soluble expand Show data source
Apperance
Off-White Low Melting Solid expand Show data source
Melting Point
90-94°C expand Show data source
Hydrophobicity(logP)
2.1 expand Show data source
2.341 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
FB3325000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
R:22-36/37/38 expand Show data source
Safety Statements
36 expand Show data source
S:25-26-36/37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Drug Control
USDEA Schedule IV expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Oral expand Show data source
Excretion
Renal expand Show data source
Half Life
2 hours expand Show data source
Metabolism
Hepatic (CYP2C19-mediated) expand Show data source
Protein Bound
60% expand Show data source
Legal Status
Schedule IV (US) expand Show data source
Pregnancy Category
C expand Show data source
Purity
95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00395 external link
Item Information
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 external link
Research Area: Neurological Disease
Biological Activity:
Sigma Aldrich - C8759 external link
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 external link
Muscle relaxant (skeletal).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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