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- Chloroxylenol
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Chloroxylenol | CAS No: 88-04-0 | GMP-certified suppliers
A medication that provides topical antiseptic and antimicrobial effects for skin disinfection, wound cleansing, and infection prevention in cuts, bites, stings, and abrasions.
Therapeutic categories
Anti-Infective AgentsAnti-Infective Agents, LocalAntiparasitic AgentsAntiplatyhelmintic AgentsAntiseptics and DisinfectantsBenzene Derivatives
Generic name
Chloroxylenol
Molecule type
small molecule
CAS number
88-04-0
DrugBank ID
DB11121
Approval status
Approved drug
ATC code
D08AE05
Primary indications
- 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
Product Snapshot
- Chloroxylenol is available in multiple topical formulations including creams, gels, liquids, ointments, soaps, sprays, and kits for cutaneous and auricular routes
- It is primarily used as a skin antiseptic for applications such as cuts, bites, stings, abrasions, and hand cleaning
- The product is approved for use in key regulatory markets including the US and Canada
Clinical Overview
Chloroxylenol (CAS 88-04-0), also known as para-chloro-meta-xylenol (PCMX), is an antiseptic and disinfectant agent primarily indicated for topical use in skin disinfection. It is commonly applied to cuts, bites, stings, abrasions, and as an antiseptic hand cleaner. It is also utilized in wound cleansing and surface disinfection, including surgical instruments. Chloroxylenol is included on the World Health Organization’s List of Essential Medicines, reflecting its established role in infection control.
Pharmacologically, chloroxylenol belongs to the class of meta-cresols, aromatic compounds characterized by a benzene ring substituted with methyl and hydroxyl groups. Its antiseptic activity is attributable to its phenolic structure, which confers bactericidal effects predominantly against Gram-positive bacteria, although various Gram-negative bacteria are also susceptible at appropriate concentrations.
The mechanism of action involves the interaction of the hydroxyl groups in chloroxylenol with bacterial cell membrane proteins. This interaction disrupts membrane integrity, resulting in leakage of intracellular contents. Subsequently, chloroxylenol penetrates the bacterial cell, binding to and inactivating essential proteins and enzymes, leading to loss of cellular function. At elevated concentrations, chloroxylenol causes coagulation of proteins and nucleic acids within the bacteria, precipitating rapid cell death.
Key pharmacokinetic parameters such as absorption, distribution, metabolism, and excretion (ADME) profiles are limited due to its primary topical use and minimal systemic absorption under standard therapeutic application. However, chloroxylenol is largely renally excreted when systemic exposure occurs.
Safety considerations include potential skin irritation or hypersensitivity reactions, especially with prolonged use or on damaged skin. It is contraindicated in individuals with known hypersensitivity to phenolic compounds. Toxicity primarily arises from ingestion or inappropriate use, necessitating careful formulation and labeling.
Chloroxylenol is incorporated in various healthcare and household antiseptic products worldwide. For API procurement, suppliers should ensure compliance with pharmacopeial standards related to purity, assay, and residual solvents. Given the API’s application in medical and hygienic products, sourcing should prioritize manufacturers with robust quality management systems and relevant regulatory approvals to ensure consistent product safety and efficacy.
Pharmacologically, chloroxylenol belongs to the class of meta-cresols, aromatic compounds characterized by a benzene ring substituted with methyl and hydroxyl groups. Its antiseptic activity is attributable to its phenolic structure, which confers bactericidal effects predominantly against Gram-positive bacteria, although various Gram-negative bacteria are also susceptible at appropriate concentrations.
The mechanism of action involves the interaction of the hydroxyl groups in chloroxylenol with bacterial cell membrane proteins. This interaction disrupts membrane integrity, resulting in leakage of intracellular contents. Subsequently, chloroxylenol penetrates the bacterial cell, binding to and inactivating essential proteins and enzymes, leading to loss of cellular function. At elevated concentrations, chloroxylenol causes coagulation of proteins and nucleic acids within the bacteria, precipitating rapid cell death.
Key pharmacokinetic parameters such as absorption, distribution, metabolism, and excretion (ADME) profiles are limited due to its primary topical use and minimal systemic absorption under standard therapeutic application. However, chloroxylenol is largely renally excreted when systemic exposure occurs.
Safety considerations include potential skin irritation or hypersensitivity reactions, especially with prolonged use or on damaged skin. It is contraindicated in individuals with known hypersensitivity to phenolic compounds. Toxicity primarily arises from ingestion or inappropriate use, necessitating careful formulation and labeling.
Chloroxylenol is incorporated in various healthcare and household antiseptic products worldwide. For API procurement, suppliers should ensure compliance with pharmacopeial standards related to purity, assay, and residual solvents. Given the API’s application in medical and hygienic products, sourcing should prioritize manufacturers with robust quality management systems and relevant regulatory approvals to ensure consistent product safety and efficacy.
Identification & chemistry
| Generic name | Chloroxylenol |
|---|---|
| Molecule type | Small molecule |
| CAS | 88-04-0 |
| UNII | 0F32U78V2Q |
| DrugBank ID | DB11121 |
Pharmacology
| Summary | Chloroxylenol is a phenolic antiseptic agent that exerts bactericidal effects by disrupting bacterial cell membranes through interactions with membrane proteins, leading to leakage of cellular contents and inhibition of enzymatic functions. At higher concentrations, it induces coagulation of bacterial proteins and nucleic acids, resulting in rapid bacterial cell death. It is primarily used for topical antimicrobial applications against a broad spectrum 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 . |
| Pharmacodynamics | 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 . |
ADME / PK
| Absorption | 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 . |
|---|---|
| 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 [L1989, L1993]. Alternatively, some product monographs liken chloroxylenol to a similar liquid antiseptic, triclosan, whose calculated urinary excretion half-life in man is approximately 10 hours . |
| 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 . |
| Metabolism | 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 | The major route of excretion is likely in urine [L1993, L1992], although some amounts may be found in bile and traces in exhaled air . |
| 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 [L1989, L1993]. |
| Clearance | 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 [L1989, L1993]. 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 . |
Formulation & handling
- Chloroxylenol is a small molecule API primarily formulated for topical and ophthalmic applications, with limited use in oral and inhalation routes.
- The compound is a liquid with moderate lipophilicity and low water solubility, necessitating consideration for solubilization and formulation stability in aqueous vehicles.
- Formulations should ensure protection from oxidation and microbial contamination due to its phenolic structure, with typical use in soaps, lotions, gels, and solutions.
Regulatory status
| Lifecycle | The active pharmaceutical ingredient (API) is experiencing market maturity in the US and Canada, with key patents having expired, allowing for increased generic competition in these regions. Ongoing regulatory approvals continue to shape its commercial availability. |
|---|
| Markets | US, Canada |
|---|
Supply Chain
| Supply chain summary | The Chloroxylenol supply landscape is characterized by multiple originator companies producing branded antimicrobial and first aid products primarily in the US and Canadian markets. Branded products have a significant presence in these regions, reflecting established market penetration. Patent expirations in this category suggest the existence of generic competition, supporting a diversified sourcing environment. |
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Safety
| Toxicity | 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 . |
|---|
High Level Warnings:
- 1
- Chloroxylenol exhibits low systemic toxicity at exposure levels typical of industrial handling
- 2
Chloroxylenol is a type of Anti-infective Agents
Anti-infective agents are a vital category of pharmaceutical active pharmaceutical ingredients (APIs) used in the treatment of various infectious diseases. These agents play a crucial role in combating bacterial, viral, fungal, and parasitic infections. The demand for effective anti-infective APIs has grown significantly due to the increasing prevalence of drug-resistant microorganisms.
Anti-infective APIs encompass a wide range of substances, including antibiotics, antivirals, antifungals, and antiparasitics. Antibiotics are particularly important in fighting bacterial infections and are further categorized into different classes based on their mode of action and target bacteria. Antivirals are designed to inhibit viral replication and are essential in the treatment of viral infections such as influenza and HIV. Antifungals combat fungal infections, while antiparasitics are used to eliminate parasites that cause diseases like malaria and helminthiasis.
The development and production of high-quality anti-infective APIs require stringent manufacturing processes and adherence to regulatory standards. Pharmaceutical companies invest heavily in research and development to discover new and more effective anti-infective agents. Additionally, ensuring the safety, efficacy, and stability of these APIs is of utmost importance.
The global market for anti-infective APIs is driven by factors such as the rising incidence of infectious diseases, the emergence of new and drug-resistant pathogens, and the growing demand for improved healthcare infrastructure. Continuous advancements in pharmaceutical technology and the development of innovative drug delivery systems further contribute to the expansion of this market.
In conclusion, anti-infective agents are a critical category of pharmaceutical APIs that play a pivotal role in treating infectious diseases. Their effectiveness in combating various types of infections makes them essential components in the arsenal of modern medicine.
