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Identification
NameChlorphenesin
Accession NumberDB00856  (APRD00867)
TypeSmall Molecule
GroupsApproved, Vet Approved, Withdrawn
Description

A centrally acting muscle relaxant. Its mode of action is unknown. Chlorphenesin is not available in the United States.

Structure
Thumb
Synonyms
3-(4-Chlorophenoxy)-1,2-propanediol
3-(P-Chlorophenoxy)-1,2-propanediol
3-(P-Chlorophenoxy)propane-1,2-diol
Chlorphenesin
Chlorphénésine
Chlorphenesinum
Clorfenesina
Glycerol alpha-P-chlorophenyl ether
P-Chlorophenyl-alpha-glyceryl ether
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mycil Creamcream10 mgtopicalAllen & Hanburys A Glaxo Canada Ltd. Co.1948-12-311996-09-10Canada
Mycil Powderpowder10 mgtopicalAllen & Hanburys A Glaxo Canada Ltd. Co.1951-12-311996-09-10Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mycil Cream 1%cream1.0 %topicalWellspring Pharmaceutical Canada Corp1996-04-302004-07-19Canada
Mycil Powder 1%powder1 %topicalRoberts Pharmaceutical Canada Inc.1996-07-301999-08-11Canada
Unapproved/Other Products Not Available
International Brands
NameCompany
KolpicortinNot Available
MaolateUpJohn
RinlaxerNot Available
Brand mixtures
NameLabellerIngredients
AnivyAllen & Hanburys A Glaxo Canada Ltd. Co.
Salts
Name/CASStructureProperties
Chlorphenesin carbamate
ThumbNot applicableDBSALT001343
Categories
UNIII670DAL4SZ
CAS number104-29-0
WeightAverage: 202.635
Monoisotopic: 202.039671925
Chemical FormulaC9H11ClO3
InChI KeyInChIKey=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
IUPAC Name
3-(4-chlorophenoxy)propane-1,2-diol
SMILES
OCC(O)COC1=CC=C(Cl)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenol ethers
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenol ether
  • Halobenzene
  • Chlorobenzene
  • Alkyl aryl ether
  • Aryl halide
  • Aryl chloride
  • Secondary alcohol
  • 1,2-diol
  • Ether
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed, 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.
PharmacodynamicsChlorphenesin is a muscle relaxant. It blocks nerve impulses (or pain sensations) that are sent to the brain.
Mechanism of actionThe 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.
Related Articles
AbsorptionRapid and complete.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. 85% of a dose excreted within 24 hours as the glucuronide metabolite.

Route of eliminationNot Available
Half life2.3-5 hours
ClearanceNot Available
ToxicitySymptoms of a chlorphenesin overdose include drowsiness and nausea.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9803
Blood Brain Barrier+0.6433
Caco-2 permeable-0.5562
P-glycoprotein substrateNon-substrate0.5768
P-glycoprotein inhibitor INon-inhibitor0.8531
P-glycoprotein inhibitor IINon-inhibitor0.9212
Renal organic cation transporterNon-inhibitor0.8694
CYP450 2C9 substrateNon-substrate0.8815
CYP450 2D6 substrateNon-substrate0.8373
CYP450 3A4 substrateNon-substrate0.7335
CYP450 1A2 substrateInhibitor0.6099
CYP450 2C9 inhibitorNon-inhibitor0.9114
CYP450 2D6 inhibitorNon-inhibitor0.9292
CYP450 2C19 inhibitorNon-inhibitor0.6201
CYP450 3A4 inhibitorNon-inhibitor0.9412
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8428
Ames testNon AMES toxic0.7102
CarcinogenicityNon-carcinogens0.8053
BiodegradationNot ready biodegradable0.8233
Rat acute toxicity2.1025 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8938
hERG inhibition (predictor II)Non-inhibitor0.8296
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
PackagersNot Available
Dosage forms
FormRouteStrength
Ointmenttopical
Creamtopical10 mg
Creamtopical1.0 %
Powdertopical10 mg
Powdertopical1 %
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point86–92Salim, E.F., Booth, R.E. (1967). "Qualitative and quantitative tests for chlorphenesin carbamate". Journal of Pharmaceutical Sciences 56 (5): 623–4. doi:10.1002/jps.2600560516. PMID 6032776.
water solubility1E+004 mg/LMERCK INDEX (1996); less than
logP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility10.4 mg/mLALOGPS
logP1.46ALOGPS
logP1.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.58 m3·mol-1ChemAxon
Polarizability20.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Parker, H.E.; U S . Patent 3,214,336; October 26, 1965; assigned to The Upjohn Company.
Collins, R.J. and Matthews, R.J.; US. Patent 3,161,567; December 15, 1964; assigned to The Upjohn Company.

General References
  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:4105542 ]
  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:6503049 ]
  3. Dalessio DJ: Medical treatment of the major neuralgias. Semin Neurol. 1988 Dec;8(4):286-90. [PubMed:3074423 ]
External Links
ATC CodesD01AE07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (35.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Not Available
Gene Name:
CYP2B
Uniprot ID:
Q14097
Molecular Weight:
43147.81 Da
References
  1. Jarukamjorn K, Sakuma T, Nemoto N: Discriminating activation of CYP2B9 expression in male C57BL/6 mouse liver by beta-estradiol. Biochem Biophys Res Commun. 2000 Dec 9;279(1):288-92. [PubMed:11112454 ]
  2. Nims RW, Lubet RA, Fox SD, Jones CR, Thomas PE, Reddy AB, Kocarek TA: Comparative pharmacodynamics of CYP2B induction by DDT, DDE, and DDD in male rat liver and cultured rat hepatocytes. J Toxicol Environ Health A. 1998 Mar 27;53(6):455-77. [PubMed:9537282 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Holloway AC, Stys KA, Foster WG: DDE-induced changes in aromatase activity in endometrial stromal cells in culture. Endocrine. 2005 Jun;27(1):45-50. [PubMed:16077170 ]
  2. Younglai EV, Holloway AC, Lim GE, Foster WG: Synergistic effects between FSH and 1,1-dichloro-2,2-bis(P-chlorophenyl)ethylene (P,P'-DDE) on human granulosa cell aromatase activity. Hum Reprod. 2004 May;19(5):1089-93. Epub 2004 Apr 7. [PubMed:15070871 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Medina-Diaz IM, Arteaga-Illan G, de Leon MB, Cisneros B, Sierra-Santoyo A, Vega L, Gonzalez FJ, Elizondo G: Pregnane X receptor-dependent induction of the CYP3A4 gene by o,p'-1,1,1,-trichloro-2,2-bis (p-chlorophenyl)ethane. Drug Metab Dispos. 2007 Jan;35(1):95-102. Epub 2006 Oct 11. [PubMed:17035600 ]
  2. Petersen MS, Halling J, Damkier P, Nielsen F, Grandjean P, Weihe P, Brosen K: Polychlorinated biphenyl (PCB) induction of CYP3A4 enzyme activity in healthy Faroese adults. Toxicol Appl Pharmacol. 2007 Oct 15;224(2):202-6. Epub 2007 Jul 14. [PubMed:17692354 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xanthine oxidase activity
Specific Function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular Weight:
146422.99 Da
References
  1. Springer RH, Dimmitt MK, Novinson T, O'Brien DE, Robins RK, Simon LN, Miller JP: Synthesis and enzymic activity of some novel xanthine oxidase inhibitors. 3-Substituted 5,7-dihydroxypyrazolo(1,5-alpha)pyrimidines. J Med Chem. 1976 Feb;19(2):291-6. [PubMed:2778 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. Fernandez P, Guillen MI, Gomar F, Aller E, Molina P, Alcaraz MJ: A novel cyclo-oxygenase-2 inhibitor modulates catabolic and antiinflammatory mediators in osteoarthritis. Biochem Pharmacol. 2004 Aug 1;68(3):417-21. [PubMed:15242808 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Westlake GE, Bunyan PJ, Stanley PI, Walker CH: The effects of 1,1-di(p-chlorophenyl)-2-chloroethylene on plasma enzymes and blood constituents in the Japanese quail. Chem Biol Interact. 1979 May;25(2-3):197-210. [PubMed:466732 ]
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Drug created on June 13, 2005 07:24 / Updated on November 27, 2015 12:59