- Accession Number
- Small Molecule
Chloroxylenol, also known as para-chloro-meta-xylenol (PCMX), is an antiseptic and disinfectant agent used for skin disinfection and cleaning surgical instruments. It is also commonly used in antibacterial soaps, wound-cleansing applications and household antiseptics. The halophenol is shown to be most effective against Gram positive bacteria where it disrupts the cell wall due to its phenolic nature . Chloroxylenol is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.
- Active Moieties
Name Kind UNII CAS InChI Key Phenol unknown 339NCG44TV 108-95-2 ISWSIDIOOBJBQZ-UHFFFAOYSA-N
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End 1012 Antimicrobial Soap 3 mg/1mL Topical Abc Compounding Co. Inc. 2013-05-01 Not applicable 986 Antiseptic Hand Soap-lot 0.5% Lotion 0.5 % Topical Fuller Brush/Les Brosses Fuller 1994-12-31 1995-08-01 ACQUAINT Antibacterial Foam Handwash Liquid 0.003 mg/1mL Topical GOJO Industries, Inc. 2004-09-09 Not applicable Acute Kare Hand Sp. Solution 0.5 g/100mL Topical Deb Canada 2017-03-01 2017-03-01 Acute-Kare Healthcare Personnel Handwash Soap 1 g/100mL Topical Deb Canada 2018-02-01 Not applicable Acute-Kare Healthcare Personnel Handwash Soap 1 g/100mL Topical STERIS Corporation 1995-01-17 Not applicable adriana Gold Liquid 0.3 g/100mL Topical Ostl, Inc. 2018-01-31 Not applicable ADVANTAGE CHEMICAL Premium Antibacterial Foaming Hand So ap Liquid 0.005 mg/1mL Topical Advantage Chemical, Inc. 2015-04-15 Not applicable Aero CleansE2 Antibacterial Liquid 2.1 mL/100mL Topical Deb Canada 2010-01-01 Not applicable Aero Florafree Antibacterial Liquid 0.5 mL/100mL Topical Deb Canada 2010-01-01 Not applicable
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Absorbine Jr Extra Strength Liniment Chloroxylenol (0.5 %) + Menthol (4.0 %) Liquid Topical Clarion Brands, Llc 1992-12-31 Not applicable Absorbine Jr Liniment Chloroxylenol (0.5 %) + Menthol (1.25 %) Liquid Topical Clarion Brands, Llc 1993-12-31 Not applicable Absorbine Power Gel Chloroxylenol (.5 %) + Menthol (4 %) Gel Topical W.F. Young, Inc. 1993-12-31 Not applicable Acne Aid Gel Chloroxylenol (.375 %) + Octasulfur (2.5 %) + Resorcinol (1.25 %) Gel Topical Stiefel Laboratories, Inc. 1966-12-31 1998-07-09 Acropole Bleu Chloroxylenol (.15 %) + Phenoxyethanol (.45 %) Jelly Topical Parall LtÉe 1997-10-01 2001-07-23 Antimicrobial Chloroxylenol (0.45 g/100mL) + Triclosan (0.06 g/100mL) Soap Topical Sky Systems Co., Inc 1990-12-10 Not applicable Blistex Foille Medicated First Aid Chloroxylenol (0.1 g/100g) + Benzocaine (5 g/100g) Ointment Topical Blistex Corporation 2013-03-05 Not applicable Contend Anti-bacterial Gel Skin Cleanser Chloroxylenol (.15 %) + Triclosan (.15 %) Gel Topical Sbs Products 1993-12-31 1997-07-23 Cosmos Hv Chloroxylenol (.15 %) + Phenoxyethanol (.45 %) Liquid Topical Parall LtÉe 1996-12-18 2004-05-25 D-COL Personal Hygiene Convenience kit Chloroxylenol (2.4 mg/1mL) + Pyrithione zinc (10 mg/1mL) Kit D-COL Inc 2018-05-30 Not applicable
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Cortaine -B Aqueous Chloroxylenol (1 mg/1mL) + Hydrocortisone (10 mg/1mL) + Pramoxine hydrochloride (10 mg/1mL) Solution / drops Auricular (otic) Physicians Total Care, Inc. 2010-09-09 2013-01-15 Cortane-B Chloroxylenol (1 mg/1mL) + Hydrocortisone (10 mg/1mL) + Pramoxine hydrochloride (10 mg/1mL) Lotion Topical Blansett Pharmacal Co 2017-03-20 Not applicable Hydro Ear Chloroxylenol (1 mg/1mL) + Benzalkonium chloride (0.1 mg/1mL) + Hydrocortisone (10 mg/1mL) + Pramoxine hydrochloride (10 mg/1mL) Solution / drops Auricular (otic) Hi Tech Pharmacal Co., Inc. 2002-08-01 2011-10-27 MyOxin Chloroxylenol (1 mg/1mL) + Benzocaine (15 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) Solution Topical GM Pharamceuticals, Inc 2011-08-01 2013-02-14 Oti Rx Chloroxylenol (1 mg/1mL) + Hydrocortisone (10 mg/1mL) + Pramoxine hydrochloride (10 mg/1mL) Liquid Auricular (otic) Breckenridge Pharmaceutical, Inc. 2003-08-01 2012-01-31 Oticin Chloroxylenol (0.01 g/10mL) + Pramoxine hydrochloride (0.1 g/10mL) Solution / drops Auricular (otic) Teral, Inc. 2009-11-12 2015-09-28 Oticin HC Ear Drops Chloroxylenol (0.01 g/10mL) + Hydrocortisone (0.1 g/10mL) + Pramoxine hydrochloride (0.01 g/10mL) Solution / drops Auricular (otic) Teral, Inc. 2009-11-12 2015-09-28 Oto End 10 Chloroxylenol (1 mg/1mL) + Hydrocortisone (10 mg/1mL) + Pramoxine hydrochloride (10 mg/1mL) Solution / drops Auricular (otic) Larken Laboratories, Inc. 2007-10-12 2015-09-28 Pramoxine-HC Chloroxylenol (1 mg/1mL) + Hydrocortisone (10 mg/1mL) + Pramoxine hydrochloride (10 mg/1mL) Solution / drops Auricular (otic) Ascend Laboratories, LLC 2011-09-26 2016-04-11 Pramoxine-HC Chloroxylenol (1 mg/1mL) + Hydrocortisone (10 mg/1mL) + Pramoxine hydrochloride (10 mg/1mL) Liquid Auricular (otic) Kylemore Pharmaceuticals, LLC 2010-01-05 2011-03-16
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antiparasitic Agents
- Antiplatyhelmintic Agents
- Antiseptics and Disinfectants
- Benzene Derivatives
- Hydrocarbons, Chlorinated
- Hydrocarbons, Halogenated
- Miscellaneous Local Anti-infectives
- Phenol and Derivatives
- CAS number
- Average: 156.61
- Chemical Formula
- InChI Key
- IUPAC Name
The predominant medical applications for which chloroxylenol is formally indicated for therapeutic use is as an application to the skin for use in cuts, bites, stings, abrasions, and for use as antiseptic hand cleaner .
Chloroxylenol is a substituted phenol which has been widely used for many years as an ingredient of antiseptic and disinfectant products intended for external use . It is known to be bactericidal in low concentration to a wide range of Gram positive and Gram negative bacteria .
- Mechanism of action
As a phenol antiseptic, it is believed that the hydroxyl -OH groups of the chloroxylenol molecule binds to certain proteins on the cell membrane of bacteria, and disrupts the membrane so as to allow the contents of the bacterial cell to leak out . This allows chloroxylenol to enter the bacterial cell to bind further with more proteins and enzymes to disable the cell's functioning . At particularly high concentrations of chloroxylenol, the protein and nucleic acid content of targeted bacterial cells become coagulated and cease to function, leading to rapid cell death .
No chloroxylenol was detected in the blood following the dermal administration of 2 g of p-chloroxylenol in an ethanol/olive oil vehicle in human subjects . After a dose of 5 g, only traces were found, after 8 g, 1 mg % (1 mg/dL) was found in the blood after 3 hours, and 4 mg % (4 mg/dL) after 24 hours . After a dose of 20 g, 4 mg % (4 mg/dL) was measured after half an hour, and 1 mg % (1 mg/dL) was present at 72 hours .
For antiseptic purposes, chloroxylenol is considered to be well-absorbed when applied to the skin .
- Volume of distribution
The only data available regarding the volume of distribution of chloroxylenol is the mean Vss of 22.45 L determined after 200 mg intravenous single dose of chloroxylenol was administered to healthy mongrel dog subjects [6, 8].
- Protein binding
One study determined the protein binding of chloroxylenol to be approximately 85.2% +/- 2.32% for serum albumin and 89.8% +/- 2.99% for whole human serum .
Certain animal studies have shown that following dermal application of chloroxylenol, that the absorption was rapid with a Cmax = 1-2 hours, and that the administered substance was excreted via the kidney with almost complete elimination within 24 hours . The primary metabolites discovered in the excreted urine were glucuronides and sulfates . Some chloroxylenol monographs liken its pharmacokinetic profile to that of another antiseptic - triclosan - which is rapidly excreted in the urine also as a glucuronide metabolite, as observed in the human model .
Moreover, In one human subject administered 5 mg intragluteally, 14% was excreted with glucuronic acid and 17% with sulfuric acid at 3 days .
Any chloroxylenol absorbed into the body is likely extensively metabolized by the liver and rapidly excreted, mainly in the urine, as sulphate and glucuronide conjugates .
- Route of elimination
- Half life
One study estimated the mean terminal half-life and mean residence time after a 200 mg intravenous single dose of chloroxylenol in healthy mongrel dog subjects to be 1.7 and 1.69 hours, respectively [6, 8]. Alternatively, some product monographs liken chloroxylenol to a similar liquid antiseptic, triclosan, whose calculated urinary excretion half-life in man is approximately 10 hours .
The only data available regarding the clearance of chloroxylenol is the mean clearance rate of 13.76 L/hr following a 200 mg intravenous single dose of the substance into healthy mongrel dog subjects [6, 8].
Moreover, in another study, when 8 g of chloroxylenol was administered dermal on a human subject in an alcohol/glycerin vehicle, 11% was excreted in 48 hours .
As chloroxylenol is predominantly employed as an active ingredient in various liquids or creams as cleaners, disinfectants, or antiseptics that are generally designed to be used topically, it is widely accepted that the use of such liquids - when used appropriately - is unlikely to present a sufficient volume that could be ingested to cause any medical problems . In the event of accidental eye contact, was with Luke warm water .
Chloroxylenol is known to have a low systemic toxicity, even at dosage levels many times higher that those likely to be absorbed during normal usage of the agent .
- Affected organisms
- Humans and other mammals
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- General References
- McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev. 1999 Jan;12(1):147-79. [PubMed:9880479]
- Judis J: Binding of selected phenol derivatives to human serum proteins. J Pharm Sci. 1982 Oct;71(10):1145-7. [PubMed:7143213]
- ZONDEK B, FINKELSTEIN M: Blood concentration of P-chloro-xylenol in man following parenteral, percutaneous and rectal application. Proc Soc Exp Biol Med. 1946 Feb;61:200-2. [PubMed:21017619]
- Zondek B, Shapiro B: Fate of halogenated phenols in the organism. Biochem J. 1943;37(5):592-5. [PubMed:16747702]
- US EPA Reregistration Eligibility Decision (RED): Chloroxylenol [Link]
- Exponent FDA Consumer Antispetics Rule: FDA Request for Data on Safety and Efficacy of Chloroxylenol [Link]
- Electronic Medicines Compendium: Dettol (Chloroxylenol) Antiseptic Cream Monograph [Link]
- NLM Toxnet: Chloroxylenol [Link]
- Electronic Medicines Compendium: Dettol (chloroxylenol) Liquid Monograph [Link]
- External Links
- ATC Codes
- D08AE05 — Chloroxylenol
- AHFS Codes
- 84:04.92 — Miscellaneous Local Anti-infectives
- Download (47.9 KB)
- Clinical Trials
- Not Available
- Not Available
- Dosage forms
Form Route Strength Jelly Topical Soap Topical 1 g/100mL Liquid Topical 2.1 mL/100mL Liquid Topical 1.49 % Lotion Topical 1.0 % Soap Topical 0.005 mL/1mL Soap Topical 250 g/1000mL Solution Topical 1.5 g/100mL Liquid Topical .3 mg/1mL Liquid Topical 0.5 % Liquid Topical 6.046 g/1L Soap Topical 40 g/1kg Soap Topical .3 g/100g Soap Topical 5 mL/1000mL Gel Topical 1.0 % Soap Topical 2.5 mg/1mL Soap Topical 6.10 g/1L Soap Topical 4 g/1000mL Gel Topical 10 mg/1mL Soap Topical 0.25 mg/100mL Gel Topical 4 mL/800mL Lotion Topical 3.6 mL/800mL Soap Topical 6.0 mg/1000mL Liquid; soap Topical .6 % Soap Topical 0.45 g/100mL Lotion Topical 0.6 % Ointment Topical 1.5 mg Liquid Topical 0.5 g/100mL Soap Topical 0.3 mg/100mL Soap Topical 25 g/100g Ointment Topical 8 mg Solution Topical 30 mg/1mL Solution Topical 3.0 % Cream Topical .25 % Soap Topical 15 g/1L Liquid Topical 3.09 mg/1mL Liquid Topical 5 mg/100mL Solution Topical 0.6 mg/100mL Soap Topical 10.1 mg/1mL Soap Topical 5 mg/1mL Soap Topical 0.003 g/1mL Liquid Topical 5 % Kit Shampoo Topical Liquid Topical 4 mg/1mL Lotion; soap Topical .5 % Liquid Topical 0.95 mL/100mL Soap Topical 0.002 g/1mL Liquid Topical .6 % Liquid Topical 4.8 % Liquid Topical 10 % Solution Topical 4.8 g/100mL Solution Topical 0.6 mL/100mL Liquid Topical 3.09 1/1mL Liquid Topical 0.15 g/100mL Sponge Topical 3 % Liquid Topical 1.1 % Solution Topical 0.9 mg/100mL Solution Topical 1.0 mg/100mL Solution Topical 100 mg/1mL Solution Topical 5.20 mg/1mL Solution Topical 5 mg/1mL Soap Topical 4 mg/1mL Liquid Topical 10 mg/1mL Solution Topical 0.8 mg/100mL Lotion Topical 0.25 % Solution Topical 8 mg/1mL Lotion; soap Topical 0.8 % Liquid Topical 15.75 g/1000mL Liquid Topical Liquid Topical 2.5 mg/1mL Liquid Topical 7.5 mg/1mL Soap Topical 2.5 g/1000mL Solution Topical 0.50 % Soap Topical 2 g/100L Solution Topical 10 mg/1mL Aerosol, foam Topical Lotion Topical .5 % Soap Topical 2.5 mg/0.001L Solution Topical 0.3 g/100mL Solution Topical 3.3 g/100g Liquid Topical 0.50 % Liquid Topical 0.663 g/221mL Liquid Topical 0.5 g/100g Liquid Topical 3.5 g/100mL Liquid Topical 0.003 mg/1mL Liquid Topical 0.50 g/100mL Liquid Topical 1.50 g/100mL Lotion Topical 10.22 g/1000mL Solution / drops Auricular (otic) Liquid Topical; Vaginal Gel Topical 5 mg/1mL Soap Topical 3 g/1000mL Soap Topical 3 mg/1mL Soap Topical 0.75 g/100mL Solution Topical 1.75 % Solution Topical 17.5 g/1L Solution Topical 0.0175 L/1L Solution Topical 0.0175 g/1mL Aerosol, foam Topical 0.005 g/1mL Liquid Topical 10.22 g/1000mL Gel Topical 0.05 g/59g Solution Topical 0.5 mg/100mL Liquid Topical 3 mg/1mL Soap Topical 10.11 g/1L Soap Topical 0.1 g/1L Soap Topical 0.5 mg/100mL Liquid Topical 5 mg/1mL Gel Topical 0.95 g/1g Liquid Topical 6 mg/1mL Soap Topical 0.95 mL/100mL Solution Topical 6.12 mg/1mL Liquid Topical 0.30 g/100g Liquid Topical 0.3 % Solution Topical Lotion Topical .25 % Liquid Topical .5 % Soap Topical 7.5 mg/1mL Liquid Auricular (otic) Cloth Topical 0.5 % Soap Topical 25 g/1000mL Sponge Topical 33 mg/1mL Sponge Topical 40 mg/1mL Soap Topical 0.005 g/1mL Soap Topical 0.1 g/100g Liquid Topical 0.6657 mg/221.8mL Liquid Topical 1.5 % Solution Topical 0.6 % Liquid Topical 0.525 % Liquid Topical .25 % Liquid Topical 0.30 kg/100kg Lotion Topical .6 % Solution Topical 6 mg/1mL Soap Topical 0.3 g/100mL Liquid Topical 0.5 mL/100mL Solution Topical 5.2 mg/1mL Solution Topical 5.25 mg/1mL Lotion Topical .3 % Liquid Topical 0.005 mg/1mL Soap Topical 6 mg/1mL Liquid Topical 2.949 g/100mL Liquid Topical 3 mL/100mL Liquid Topical 0.8 mL/100mL Lotion Topical 0.08 mg/100mL Ointment Topical Gel Topical 1 % Soap Topical 30 mg/10mL Liquid Topical .7 % Liquid Topical 5 g/1L Soap Topical 5 g/1000mL Liquid Topical 0.01 mg/1mL Liquid Topical 0.5 mg/100mL Swab Topical Soap Topical 10 mg/1mL Liquid Topical 0.0060 mg/1mL Liquid Topical 0.0060 g/1mL Cream Topical Lotion Topical Solution Topical 0.5 g/100mL Solution Topical 0.5 % Solution Topical 1.25 g/100mL Solution Topical 1.25 % Liquid Topical 1.75 % Solution Topical 33 mg/1mL Solution Topical 40 mg/1mL Solution Topical 3.3 % Solution Topical 3.3 mg/100mL Solution Topical 4 mg/100mL Lotion Topical 0.5 % Aerosol, foam Topical .5 mL/100mL Lotion Topical 0.3 % Liquid Topical 0.6 mL/100mL Liquid Topical 0.05 g/100mL Aerosol, foam Topical 5 mg/1mL Soap Topical 0.33 mg/1000mL Liquid Topical 1.0 % Aerosol Topical .1 % Solution Topical 3.82 g/100mL Liquid Topical 0.3 mL/100mL Liquid Topical 1 g/100mL Solution Topical 1 g/100mL Solution Topical 10 g/1L Lotion Topical 0.51 % Soap Topical 0.001 mg/100mL Liquid Topical 1 % Liquid Topical 12.604 g/100mL Liquid Topical 189 g/1000mL Soap Topical 3 % Liquid Topical 3 % Gel Topical .25 % Liquid Topical 2 % Soap Topical Soap Topical 2.75 g/100mL Solution Topical 2.75 % Liquid Topical 2.75 g/100mL Liquid Topical 0.3 kg/100kg Lotion Topical 1 % Liquid Topical 0.3 g/100mL Soap Topical 3.75 mg/1mL Soap Topical 0.75 g/100g Soap Topical 3.6 g/1mL Liquid Topical 3.09 g/1mL Liquid Topical 3.06 mg/1mL Gel Topical Gel Topical 0.52 g/100mL Liquid Topical 0.52 % Gel Topical 0.5 % Cloth Topical 0.5 g/100g Liquid Topical 0.6 % Liquid Topical 0.65 % Soap Topical 1 g/100g Soap Topical 5.0 mg/1mL Liquid Topical 2081980 mg/208198mL Soap Topical .5 % Liquid Topical 0.03 g/10mL Liquid Topical 0.3 g/10mL Liquid Topical 0.04 g/10mL Liquid Topical 0.04 g/10L Liquid; shampoo Topical
- Not Available
- Not Available
- Experimental Properties
Property Value Source melting point (°C) 112-116 degrees Celsius MSDS boiling point (°C) 246 degrees Celsius MSDS water solubility 0.03 g/100ml at 15 degrees Celsius, 0.5 g/100ml at 100 degrees Celsius MSDS
- Predicted Properties
Property Value Source Water Solubility 0.855 mg/mL ALOGPS logP 3.14 ALOGPS logP 3.3 ChemAxon logS -2.3 ALOGPS pKa (Strongest Acidic) 9.21 ChemAxon pKa (Strongest Basic) -6.3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 20.23 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 42.93 m3·mol-1 ChemAxon Polarizability 16.04 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon
- Predicted ADMET features
- Not Available
- Mass Spec (NIST)
- Not Available
Spectrum Spectrum Type Splash Key Mass Spectrum (Electron Ionization) MS splash10-05fu-9500000000-8bba3165beb98d883986 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 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
- This compound belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.
- Organic compounds
- Super Class
- Sub Class
- Direct Parent
- Meta cresols
- Alternative Parents
- m-Xylenes / P-chlorophenols / Chlorobenzenes / 1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Organooxygen compounds / Organochlorides / Hydrocarbon derivatives
- M-xylene / Xylene / 4-chlorophenol / M-cresol / 4-halophenol / 1-hydroxy-2-unsubstituted benzenoid / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols, monochlorobenzenes (CHEBI:34393)
Drug created on December 03, 2015 09:51 / Updated on November 16, 2018 11:28