Identification
- Summary
Chlorphenesin is a phenol ether used to treat painful muscular conditions.
- Generic Name
- Chlorphenesin
- DrugBank Accession Number
- DB00856
- Background
Not Available
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Chlorphenesin (DB00856)
- Weight
- Average: 202.635
Monoisotopic: 202.039671925 - Chemical Formula
- C9H11ClO3
- 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 α-p-chlorophenyl ether
- p-chlorophenyl-α-glyceryl ether
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.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of a chlorphenesin overdose include drowsiness and nausea.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareBaclofen Baclofen may increase the central nervous system depressant (CNS depressant) activities of Chlorphenesin. Capmatinib The serum concentration of Capmatinib can be decreased when it is combined with Chlorphenesin. Clindamycin The metabolism of Clindamycin can be increased when combined with Chlorphenesin. Clobazam The risk or severity of sedation, somnolence, and CNS depression can be increased when Clobazam is combined with Chlorphenesin. Clozapine The serum concentration of Clozapine can be decreased when it is combined with Chlorphenesin. Cyclobenzaprine The risk or severity of CNS depression can be increased when Cyclobenzaprine is combined with Chlorphenesin. Daridorexant The risk or severity of CNS depression can be increased when Chlorphenesin is combined with Daridorexant. Doxorubicin The serum concentration of Doxorubicin can be decreased when it is combined with Chlorphenesin. Fluoxetine Chlorphenesin may increase the central nervous system depressant (CNS depressant) activities of Fluoxetine. Haloperidol The risk or severity of CNS depression can be increased when Haloperidol is combined with Chlorphenesin. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mycil Cream Cream 10 mg / g Topical Allen & Hanburys A Glaxo Canada Ltd. Co. 1948-12-31 1996-09-10 Canada 
Mycil Powder Powder 10 mg / g Topical Allen & Hanburys A Glaxo Canada Ltd. Co. 1951-12-31 1996-09-10 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mycil Cream 1% Cream 1.0 % Topical Well Spring Pharmaceutical Corporation 1996-04-30 2004-07-19 Canada Mycil Powder 1% Powder 1 % Topical Roberts Pharmaceutical 1996-07-30 1999-08-11 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image (badiful) Antibacterial Wipes Chlorphenesin (2 mg/100mL) + Benzalkonium chloride (13 mg/100mL) + Cetylpyridinium chloride (5 mg/100mL) + Propylene glycol (2 mg/100mL) Swab Topical ZHANGZHOU KANGBEI HYGIENIC PRODUCTS CO., LTD. 2020-05-31 Not applicable US 
Alcohol Wet Tissue Chlorphenesin (0.05 g/100g) + Benzalkonium chloride (0.1 g/100g) + Cetylpyridinium chloride (0.05 g/100g) + Didecyldimethylammonium chloride (0.1 g/100g) + Ethanol (75 g/100g) Swab Topical SHANDONG PROVINCE RUNHE SANITARY MATERIALS CO.,LTD. 2020-04-13 Not applicable US Anivy Chlorphenesin (10 mg / g) + Benzocaine (10 mg / g) + Titanium dioxide (210 mg / g) + Zinc oxide (235 mg / g) Ointment Topical Allen & Hanburys A Glaxo Canada Ltd. Co. 1988-03-23 1996-09-10 Canada Disinfecting Wipes Chlorphenesin (0.05 g/100g) + Benzalkonium chloride (0.1 g/100g) + Cetylpyridinium chloride (0.05 g/100g) + Didecyldimethylammonium chloride (0.1 g/100g) + Isopropyl alcohol (75 g/100g) Swab Topical SHANDONG PROVINCE RUNHE SANITARY MATERIALS CO.,LTD. 2020-04-13 Not applicable US Hand Sanitizer Smells Clean Chlorphenesin (0.143 g/100mL) + Ethanol (70 mL/100mL) + Phenoxyethanol (0.143 g/100mL) Gel Topical IWANNA CORP SAS 2020-03-30 Not applicable US Medi SM 24K Gold Hydrogel Peptide Mask Pack Chlorphenesin (0.01 g/100g) + Adenosine (0.01 g/100g) + Butylene glycol (0.01 g/100g) + Chondrus crispus (0.02 g/100g) + Glycerin (0.05 g/100g) + Glycyrrhiza glabra (0.01 g/100g) + Gold (0.01 g/100g) + Nicotinamide (0.02 g/100g) + Polysorbate 20 (0.01 g/100g) + Polysorbate 60 (0.02 g/100g) + Potassium chloride (0.02 g/100g) + Propolis wax (0.01 g/100g) + Titanium dioxide (0.01 g/100g) + Xanthan gum (0.01 g/100g) Emulsion Topical Mbg Inc (Korea Institute of Science Development) 2017-11-07 2018-11-07 US Puricia Sanitizing Wipes ( Blossom) Chlorphenesin (0.05 U/100U) + Benzalkonium chloride (0.13 U/100U) + Cetylpyridinium chloride (0.05 U/100U) + Didecyldimethylammonium chloride (0.1 U/100U) + Ethanol (65 U/100U) + Phenoxyethanol (0.3 U/100U) Cloth Topical PHARMABERG INC. 2020-11-03 Not applicable US Puricia Sanitizing Wipes (Citrus) Chlorphenesin (0.05 U/100U) + Benzalkonium chloride (0.13 U/100U) + Cetylpyridinium chloride (0.05 U/100U) + Didecyldimethylammonium chloride (0.1 U/100U) + Ethanol (65 U/100U) + Phenoxyethanol (0.3 U/100U) Cloth Topical PHARMABERG INC. 2020-11-03 Not applicable US Puricia Sanitizing Wipes (Lavender) Chlorphenesin (0.05 U/100U) + Benzalkonium chloride (0.13 U/100U) + Cetylpyridinium chloride (0.05 U/100U) + Didecyldimethylammonium chloride (0.1 U/100U) + Ethanol (65 U/100U) + Phenoxyethanol (0.3 U/100U) Cloth Topical PHARMABERG INC. 2020-11-05 Not applicable US Puricia Sanitizing Wipes (Mint) Chlorphenesin (0.05 U/100U) + Benzalkonium chloride (0.13 U/100U) + Cetylpyridinium chloride (0.05 U/100U) + Didecyldimethylammonium chloride (0.1 U/100U) + Ethanol (65 U/100U) + Phenoxyethanol (0.3 U/100U) Cloth Topical PHARMABERG INC. 2020-11-05 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image (badiful) Antibacterial Wipes Chlorphenesin (2 mg/100mL) + Benzalkonium chloride (13 mg/100mL) + Cetylpyridinium chloride (5 mg/100mL) + Propylene glycol (2 mg/100mL) Swab Topical ZHANGZHOU KANGBEI HYGIENIC PRODUCTS CO., LTD. 2020-05-31 Not applicable US Medi SM 24K Gold Hydrogel Peptide Mask Pack Chlorphenesin (0.01 g/100g) + Adenosine (0.01 g/100g) + Butylene glycol (0.01 g/100g) + Chondrus crispus (0.02 g/100g) + Glycerin (0.05 g/100g) + Glycyrrhiza glabra (0.01 g/100g) + Gold (0.01 g/100g) + Nicotinamide (0.02 g/100g) + Polysorbate 20 (0.01 g/100g) + Polysorbate 60 (0.02 g/100g) + Potassium chloride (0.02 g/100g) + Propolis wax (0.01 g/100g) + Titanium dioxide (0.01 g/100g) + Xanthan gum (0.01 g/100g) Emulsion Topical Mbg Inc (Korea Institute of Science Development) 2017-11-07 2018-11-07 US Wet Wipes Chlorphenesin (0.1 g/100g) + Benzalkonium (0.06 g/100g) + Didecyldimethylammonium chloride (0.4 g/100g) + Ethanol (10 g/100g) + Phenoxyethanol (0.3 g/100g) Cloth Topical Sourcery Ltd 2020-06-15 Not applicable US
Categories
- ATC Codes
- D01AE07 — Chlorphenesin
- Drug Categories
- Alcohols
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Dermatologicals
- Glycols
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Peripheral Nervous System Agents
- Propylene Glycols
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Phenoxy compounds / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Secondary alcohols / 1,2-diols / Primary alcohols / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,2-diol / Alcohol / Alkyl aryl ether / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Ether / Halobenzene / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- propane-1,2-diols, monochlorobenzenes, glycol (CHEBI:3642)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- I670DAL4SZ
- CAS number
- 104-29-0
- InChI Key
- 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
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
- Malley A, Baecher L: Inhibition of histamine and SRS-A from monkey lung tissue by chlorophenesin. J Immunol. 1971 Aug;107(2):586-8. [Article]
- 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. [Article]
- Dalessio DJ: Medical treatment of the major neuralgias. Semin Neurol. 1988 Dec;8(4):286-90. [Article]
- External Links
- Human Metabolome Database
- HMDB0014994
- KEGG Compound
- C07928
- PubChem Compound
- 7697
- PubChem Substance
- 46504714
- ChemSpider
- 7411
- 2399
- ChEBI
- 3642
- ChEMBL
- CHEMBL388751
- PharmGKB
- PA164784022
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Chlorphenesin_carbamate
- MSDS
- Download (35.8 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Pharmacia and upjohn co
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Ointment Topical Swab Topical Gel Topical Emulsion Topical Cream Topical 10 mg / g Cream Topical 1.0 % Powder Topical 10 mg / g Powder Topical 1 % Cloth Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 86–92 Salim, 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 solubility 1E+004 mg/L MERCK INDEX (1996); less than logP 1.2 Not Available - Predicted Properties
Property Value Source Water Solubility 10.4 mg/mL ALOGPS logP 1.46 ALOGPS logP 1.1 Chemaxon logS -1.3 ALOGPS pKa (Strongest Acidic) 13.62 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.69 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 49.58 m3·mol-1 Chemaxon Polarizability 20.1 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9803 Blood Brain Barrier + 0.6433 Caco-2 permeable - 0.5562 P-glycoprotein substrate Non-substrate 0.5768 P-glycoprotein inhibitor I Non-inhibitor 0.8531 P-glycoprotein inhibitor II Non-inhibitor 0.9212 Renal organic cation transporter Non-inhibitor 0.8694 CYP450 2C9 substrate Non-substrate 0.8815 CYP450 2D6 substrate Non-substrate 0.8373 CYP450 3A4 substrate Non-substrate 0.7335 CYP450 1A2 substrate Inhibitor 0.6099 CYP450 2C9 inhibitor Non-inhibitor 0.9114 CYP450 2D6 inhibitor Non-inhibitor 0.9292 CYP450 2C19 inhibitor Non-inhibitor 0.6201 CYP450 3A4 inhibitor Non-inhibitor 0.9412 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8428 Ames test Non AMES toxic 0.7102 Carcinogenicity Non-carcinogens 0.8053 Biodegradation Not ready biodegradable 0.8233 Rat acute toxicity 2.1025 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8938 hERG inhibition (predictor II) Non-inhibitor 0.8296
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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. Ha...
- Gene Name
- XDH
- Uniprot ID
- P47989
- Uniprot Name
- Xanthine dehydrogenase/oxidase
- Molecular Weight
- 146422.99 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at April 27, 2021 13:17