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Identification
Name Chlorphenesin
Accession Number DB00856 (APRD00867)
Type small molecule
Groups approved
Description

A centrally acting muscle relaxant. Its mode of action is unknown. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1203)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • alpha-Glyceryl ether
  • Chlorophenesin
  • Chlorphenesine [INN-French]
  • Chlorphenesinum [INN-Latin]
  • Clorfenesina [INN-Spanish]
  • p-Chlorophenyl
  • p-Chlorophenyl glyceryl ether
Brand names
  • Adermykon
  • Demykon
  • Gechophen
  • Gecophen
  • Maolate
  • Mycil
Brand name mixtures
  • Anivy (Benzocaine + Chlorphenesin + Titanium Dioxide + Zinc Oxide)
Categories
  • Muscle Relaxants, Central
CAS number 104-29-0
Weight Average: 202.635
Monoisotopic: 202.039671925
Chemical Formula C9H11ClO3
InChI Key InChIKey=MXOAEAUPQDYUQM-UHFFFAOYSA-N
InChI
InChI=1S/C9H11ClO3/c10-7-1-3-9(4-2-7)13-6-8(12)5-11/h1-4,8,11-12H,5-6H2
Plain Text
IUPAC Name
3-(4-chlorophenoxy)propane-1,2-diol
SMILES
OCC(O)COC1=CC=C(Cl)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Ethers
  • Halobenzenes
  • Anisoles
  • Phenyl Esters
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Alcohols and Polyols
  • Aromatic compounds
  • Anisoles
  • Phenyl Esters
Pharmacology
Indication Used, along with rest and physical therapy, to treat injuries and other painful muscular conditions. Investigated for use in trigeminal neuralgia (tic douloureux), a neuropathic disorder characterized by severe facial pain. Was investigated as a modulator of histamine release.
Pharmacodynamics Chlorphenesin is a muscle relaxant. It blocks nerve impulses (or pain sensations) that are sent to the brain.
Mechanism of action The mechanism of action of chlorphenesin is not well defined, and its effects are measured mainly by subjective responses. It is known that chlorphenesin acts in the central nervous system (CNS) rather than directly on skeletal muscle.
Absorption Rapid and complete.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic. 85% of a dose excreted within 24 hours as the glucuronide metabolite.
Route of elimination Not Available
Half life 2.3-5 hours
Clearance Not Available
Toxicity Symptoms of a chlorphenesin overdose include drowsiness and nausea.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 78 oC
Experimental Properties
Property Value Source
water solubility 1E+004 mg/L PhysProp
logP 1.2 PhysProp
Predicted Properties
Property Value Source
water solubility 1.04e+01 g/l ALOGPS
logP 1.46 ALOGPS
logP 1.10 ChemAxon Molconvert
logS -1.29 ALOGPS
pKa 15.56 ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 49.69 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 49.58 ChemAxon Molconvert
polarizability 20.10 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Malley A, Baecher L: Inhibition of histamine and SRS-A from monkey lung tissue by chlorophenesin. J Immunol. 1971 Aug;107(2):586-8. Pubmed
  2. Kurachi M, Aihara H: Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats. Jpn J Pharmacol. 1984 Sep;36(1):7-13. Pubmed
  3. Dalessio DJ: Medical treatment of the major neuralgias. Semin Neurol. 1988 Dec;8(4):286-90. Pubmed
External Links
Resource Link
KEGG Compound C07928 Link_out
PubChem Compound 7697 Link_out
PubChem Substance 46504714 Link_out
ChemSpider 7411 Link_out
PharmGKB PA448958 Link_out
Drug Product Database 2091496 Link_out
Drugs.com http://www.drugs.com/mtm/chlorphenesin.html Link_out
ATC Codes
  • D01AE07
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (35.8 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Comments
Drug created on June 13, 2005 07:24 / Updated on January 17, 2011 12:59

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