4-Chloro-3,5-dimethylphenol

The Uses of 4-Chloro-3,5-dimethylphenol

4-Chloro-3,5-dimethylphenol is an antiseptic and germicide. Chloroxylenol is used for mildew prevention. Chloroxylenol is also an antibacterial; antiseptic (topical and urinary).

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 .

Background

Chloroxylenol, or para-chloro-meta-xylenol (PCMX), is an antiseptic and disinfectant agent used for skin disinfection and surgical instruments. It is found 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.

Pharmacokinetics

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 .

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 .

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 .

Synthesis

A method for synthesizing 4-chloro-3, 5-dimethylphenol is characterized by comprising the following steps: under the condition that a cupric salt is used as a catalyst, 3, 5-dimethylphenol, a chlorinating agent and an oxidizing agent are reacted in an organic solvent to obtain 4-chloro-3, 5-dimethylphenol.