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General Description:

Triclocarban, identified by CAS number 101-20-2, is a notable compound with significant therapeutic applications. Triclocarban, with the chemical formula C13H9Cl3N2O is an antibacterial agent that is particularly effective against Gram-positive bacteria such as *Staphylococcus aureus*. It is a bacteriostatic compound that has been found in antibacterial soaps and other personal care products. In 2017, the US FDA prohibited the marketing of over-the-counter (OTC) consumer antiseptic wash products containing triclocarban due to negative health effects such as bacterial resistance or hormonal effects , .

Indications:

This drug is primarily indicated for: Triclocarban (TCC), or 3,4,4'-trichlorocarbanilide, is an antibacterial agent used in bar and liquid soaps and body washes . Its use in specific medical scenarios underscores its importance in the therapeutic landscape.

Metabolism:

Triclocarban undergoes metabolic processing primarily in: Blood levels after parenteral injection are low and comparison of the radioactivity and chemical determinations suggest rapid metabolism of the Triclocarban . Human metabolism of TCC involves direct glucuronidation to form N- and N'- glucuronides as well as ring hydroxylation to 2'-hydroxy-TCC and 6-hydroxy-TCC, which are further metabolized to sulfate and glucuronide conjugates. In human subjects given a single oral dose of TCC, 27% of the dose was excreted in the urine within 80 hours. About 70% of the administered dose was excreted in the feces within 5 days . The major urinary metabolites were N-glucuronides (average levels, 30 ng/mL) and a major plasma metabolite was the sulfate conjugate of 2'-OH-TCC (levels ranged from 0-20 ng/mL . The maximum plasma level occurred 2.8 hr after dosing and was 3.7 nmol-equivalents of TCC per g of plasma (approximately 1.2 ppm). Biotransformation of TCC was rapid but did not appear to involve splitting of the basic TCC structure. The major plasma metabolites were N- and N'-glucuronides of TCC which were eliminated with half-life approximately 2 hr to the urine and 2'-hydroxy-TCC sulfate and 6-hydroxy-TCC sulfate (the o-hydroxy-TCC sulfates) which were removed with half life approximately 20 hr (presumably into the bile) . This metabolic pathway ensures efficient processing of the drug, helping to minimize potential toxicity and side effects.

Absorption:

The absorption characteristics of Triclocarban are crucial for its therapeutic efficacy: A human exposure study in a small group of subjects demonstrated that a portion of the TCC present in bar soaps is absorbed through the skin and is excreted in urine as N-glucuronides . Because they are produced and used in large quantities in various products, they are absorbed into the human body of the general population . The absorption of triclocarban during a human pharmacokinetic study was estimated at 0.6% of the 70 + or - 15 mg of triclocarban in the soap used. The triclocarban-N-glucuronide urine concentration varied considerably among the study subjects, and continuous daily use of the soap led to steady-state levels of excretion . The drug's ability to rapidly penetrate into cells ensures quick onset of action.

Half-life:

The half-life of Triclocarban is an important consideration for its dosing schedule: 10 hours. This determines the duration of action and helps in formulating effective dosing regimens.

Route of Elimination:

The elimination of Triclocarban from the body primarily occurs through: The metabolism of (14)C-TCC (3,4,4'-trichlorocarbanilide) has been investigated in humans following oral exposure to 2.2 mumol/kg. Fecal elimination (70% of dose) was complete at the 120 hour point after administration and the urinary excretion (27% of dose) was complete after 80 hours post-administration . Urinary glucuronides appear to be valuable biomarkers of triclocarban exposure . Understanding this pathway is essential for assessing potential drug accumulation and toxicity risks.

Clearance:

The clearance rate of Triclocarban is a critical factor in determining its safe and effective dosage: After a pharmacokinetic study in man, radioactivity was rapidly cleared from blood after intravenous administrations of (14)C-triclocarban in propylene glycol with a blood clearance half-life measured to be 8.6 hours . It reflects the efficiency with which the drug is removed from the systemic circulation.

Pharmacodynamics:

Triclocarban exerts its therapeutic effects through: The antimicrobial mechanism underlying the bacteriostatic and bactericidal effects of triclocarban is believed to be an unspecific adsorption to cell membranes and interruption of their function. As a result, the growth of gram-positive as well as gram-negative bacteria is inhibited . The drug's ability to modulate various physiological processes underscores its efficacy in treating specific conditions.

Mechanism of Action:

Triclocarban functions by: Triclocarban is a triclosan analog with an antibacterial activity. Triclocarban exerts its effect by inhibiting the activity of _enoyl-(acyl-carrier protein) (ACP) reductase_, which is ubiquitously distributed in bacteria, fungi and various plants. ACP reductase catalyzes the last step in each cycle of fatty acid elongation in the type II fatty acid synthase systems. As a result, this agent interrupts cell membrane synthesis and leads to bacterial growth inhibition . This mechanism highlights the drug's role in inhibiting or promoting specific biological pathways, contributing to its therapeutic effects.

Toxicity:

Classification:

Triclocarban belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it, classified under the direct parent group Dichlorobenzenes. This compound is a part of the Organic compounds, falling under the Benzenoids superclass, and categorized within the Benzene and substituted derivatives class, specifically within the Halobenzenes subclass.

Categories:

Triclocarban is categorized under the following therapeutic classes: Amides, Amines, Anilides, Aniline Compounds, Anti-Infective Agents, Anti-Infective Agents, Local, Benzene Derivatives, Environmental Pollutants, Miscellaneous Local Anti-infectives, Phenylurea Compounds, Toxic Actions, Water Pollutants, Water Pollutants, Chemical. These classifications highlight the drug's diverse therapeutic applications and its importance in treating various conditions.

Experimental Properties:

Further physical and chemical characteristics of Triclocarban include:

• Water Solubility: Insoluble
• Melting Point: 491.2- 493