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General Description:

Cresol, identified by CAS number 1319-77-3, is a notable compound with significant therapeutic applications. Cresol is a hydroxytoluene that can be extracted naturally from coal tar or made synthetically. Pure cresol is a mixture of ortho-, meta-, and para- isomers. Cresols are precursors or synthetic intermediates to various other compounds and materials, including plastics, pesticides, pharmaceuticals, disinfectants, and dyes. Ingestion of cresol induces toxicity in humans and can lead to burning of the mouth and throat, abdominal pain, and/or vomiting. At concentrations normally found in the environment however, cresols do not pose any significant risk for the general population.

Indications:

This drug is primarily indicated for: The primary medical indications for cresols in general include being used as bactericides, pesticides, and disinfectants . Certain isomers of cresol, like m-cresol, may be used as inactive ingredients for the purpose of serving as a preservative in some pharmaceuticals . Its use in specific medical scenarios underscores its importance in the therapeutic landscape.

Metabolism:

Cresol undergoes metabolic processing primarily in: Once absorbed, cresols are mainly metabolized by the liver and result in metabolites that are conjugated with glucuronic acid and inorganic sulfate and excreted as conjugates in the urine . Some primary metabolites that have been documented subsequently include p-cresyl sulfate and the glucuronide p-cresol metabolite . This metabolic pathway ensures efficient processing of the drug, helping to minimize potential toxicity and side effects.

Absorption:

The absorption characteristics of Cresol are crucial for its therapeutic efficacy: In general, it is believed that cresols can be absorbed through intact skin and across respiratory and gastrointestinal linings . Although the rates and extents to which cresols are absorbed across the lungs and gastrointestinal tract do not yet appear to have been studied in detail, an in-vitro study regarding the permeability of human skin to cresols demonstrated that cresols possess permeability coefficients larger than that of phenol, which is already known to be readily absorbed across the human skin . In particular, the permeability coefficients (Kp) were approximated from the steady-state slopes of the relation between the cumulative amount of cresol isomer per unit area of membrane with time . The particular Kp values calculated for m-, o-, and p-cresol were 2.54 x 10^-4, 2.6 x 10^-4, and 2.92 x 10^-4 cm/minute, respectively . The drug's ability to rapidly penetrate into cells ensures quick onset of action.

Half-life:

The half-life of Cresol is an important consideration for its dosing schedule: There does not appear to be detailed information on the half-life of cresol in the human body ; the pharmacokinetics of cresol in the human body is usually discussed in the context of accidental exposure and ingestion and not as a formal research study. Nevertheless, various environmental and laboratory animal half-life values for administered cresol have been reported. This determines the duration of action and helps in formulating effective dosing regimens.

Protein Binding:

Cresol exhibits a strong affinity for binding with plasma proteins: P-cresyl sulfate and p-cresol, both of which are primary cresol metabolites that have been documented, have been observed to demonstrate relatively low protein binding with human serum albumin at about 13-20% binding . The affinity of p-cresyl sulfate and p-cresol toward human serum albumin is evidently moderate at 25 degrees Celsius and becomes relatively weak at physiological temperature, 37 degrees Celsius . Such protein binding largely involves van Der Waals category of interactions, and the binding sites of the two moieties are either identical or extremely close in proximity . This property plays a key role in the drug's pharmacokinetics and distribution within the body.

Route of Elimination:

The elimination of Cresol from the body primarily occurs through: The major route of excretion is likely in the urine . Understanding this pathway is essential for assessing potential drug accumulation and toxicity risks.

Volume of Distribution:

Cresol is distributed throughout the body with a volume of distribution of: One study determined the volume of distribution of p-cresol in healthy rats as being approximately 2.9 +/- 1.4 L/kg . Nevertheless, one case study reports detecting cresols in the blood (120 mg/litre), liver, brain, and urine of a human infant who passed away four hours after 20 ml of a cresol derivative had spilled on the infant's head . Otherwise, very little data about the distribution of cresols in the human body is available . This metric indicates how extensively the drug permeates into body tissues.

Clearance:

The clearance rate of Cresol is a critical factor in determining its safe and effective dosage: As colonic microbial metabolism contributes significantly to uremic retention solutes in patients with chronic kidney disease, one study estimated the clearance of p-Cresyl sulfate and the glucuronide p-cresol metabolite - both of which are metabolites of cresol and representative uremic retention solutes - in such patients. The total renal clearance of p-Cresyl sulfate was median 6.6 ml/min while that of the glucuronide p-cresol metabolite was median 98.9 ml/min . Furthermore, the free solute renal clearance of p-Cresyl sulfate and the glucuronide p-cresol metabolite were observed to be about median 190,0 ml/min and about median 136.5 ml/min, respectively . These results were obtained for a specific subject population that was comprised of 488 patients with chronic kidney disease stages 1 through 5, demonstrating a mean eGFR (ml/min per 1.73 m2) of 35 . Additionally, endogenous p-cresol is produced from tyrosine, an amino acid that is found in most proteins, by anaerobic bacteria in the intestine . It has been observed that healthy humans generally excrete an average of approximately 50 mg (out of a range of 16 to 74 mg) of such endogenously generated p-cresol daily in the urine . It reflects the efficiency with which the drug is removed from the systemic circulation.

Pharmacodynamics:

Cresol exerts its therapeutic effects through: All cresol isomers are absorbed across the respiratory and gastrointestinal tract and through the intact skin . Limited data indicate that cresols are widely distributed throughout the body after uptake . Cresols are mainly conjugated with glucuronic acid and inorganic sulfate and excreted as conjugates with the urine . At physiological pH, the conjugated metabolites are ionized to a greater extent than the parent compound, which reduces renal reabsorption and increases elimination with the urine . In addition to urinary excretion, cresols are excreted in the bile, but the most part undergoes enterohepatic circulation . There are know species differences in the specific conjugation reactions of cresol isomers and the relative amounts of glucuronide and sulfate conjugates therefore differ between species and also vary with dose . The drug's ability to modulate various physiological processes underscores its efficacy in treating specific conditions.

Mechanism of Action:

Cresol functions by: When cresol isomers are used directly as the active ingredient in bactericides or disinfectants, it appears as if much of the evidence for the mechanism of action for such phenolic germicides indicates that their effect is due to physical damage of bacterial cell membranes . Although not completely explained, some possibilities of how this effect occurs either involves the phenol germicide binding or coming into contact with and (a) causing changes in the permeability of the osmotic barrier of bacterial cell membranes, which therefore allows the escape or leakage of normal cytoplasmic constituents, (b) causing the uncoupling of cytoplasmic constituents with their subsequent leakage from the cell, or (c) a combination of these actions . This mechanism highlights the drug's role in inhibiting or promoting specific biological pathways, contributing to its therapeutic effects.

Toxicity:

Categories:

Cresol is categorized under the following therapeutic classes: Benzene Derivatives, Drugs that are Mainly Renally Excreted, Phenols, Standardized Chemical Allergen. These classifications highlight the drug's diverse therapeutic applications and its importance in treating various conditions.

Experimental Properties:

Further physical and chemical characteristics of Cresol include:

• Water Solubility: o-cresol: 2.5g/100ml / m-cresol: 2.4g/100ml / p-cresol: 1.9g/100ml
• Melting Point: o-cresol: 29.8/ m-cresol: 11.8/ p-cresol: 35.5
• Boiling Point: o-cresol: 191.0/ m-cresol: 202.0/ p-cresol: 201.9
• pKa: o-cresol: 10.287/ m-cresol: 10.09/ p-cresol: 10.26