The Different Facets of Triclocarban: A Review

Abstract

In the late 1930s and early 1940s, it was discovered that the substitution on aromatic rings of hydrogen atoms with chlorine yielded a novel chemistry of antimicrobials. However, within a few years, many of these compounds and formulations showed adverse effects, including human toxicity, ecotoxicity, and unwanted environmental persistence and bioaccumulation, quickly leading to regulatory bans and phase-outs. Among these, the triclocarban, a polychlorinated aromatic antimicrobial agent, was employed as a major ingredient of toys, clothing, food packaging materials, food industry floors, medical supplies, and especially of personal care products, such as soaps, toothpaste, and shampoo. Triclocarban has been widely used for over 50 years, but only recently some concerns were raised about its endocrine disruptive properties. In September 2016, the U.S. Food and Drug Administration banned its use in over-the-counter hand and body washes because of its toxicity. The withdrawal of triclocarban has prompted the efforts to search for new antimicrobial compounds and several analogues of triclocarban have also been studied. In this review, an examination of different facets of triclocarban and its analogues will be analyzed.

Kinase Inhibitor Library Screening Identifies the Cancer Therapeutic Sorafenib and Structurally Similar Compounds as Strong Inhibitors of the Fungal Pathogen Histoplasma capsulatum

“…Sorafenib and several of the compounds identified in our screen are diarylureas, which has served as an important molecular scaffold in anticancer drug development [50,51]. A growing body of work shows a strong potential for the use of the diarylurea scaffold in the development of antiviral, antiparasite, antibacterial and antifungal compounds [52][53][54]. Sorafenib in particular is reported to possess activity against drug-resistant Staphylococcus aureus and to interfere with replication of New World alphaviruses through a mechanism that is independent of host cell kinase inhibition [55].…”

Determination of Parabens, Bisphenol A and Its Analogs, Triclosan, and Benzophenone-3 Levels in Human Urine by Isotope-Dilution-UPLC-MS/MS Method Followed by Supported Liquid Extraction

“…One epidemiologic study also indicated that PrPB is considerably associated with DNA damage in human sperm [12]. Furthermore, two antibacterial ingredients, TCS and triclocarban (TCCB), are frequently used in >2000 products, including PCPs (e.g., toothpaste and hand soap); detergents and plastics are also EDCs, and are found in a wide variety of matrixes worldwide [13,14]. Dermal absorption from PCPs is the primary route for human exposure to TCCB or TCS because of their high concentrations (0.1-0.3% [w/w]) [13][14][15]; both have been detected in human blood and urine [13,14].…”

Benzothiazole-Containing Analogues of Triclocarban with Potent Antibacterial Activity

“…Triclocarban (TCC, Figure 1), N-(4-chlorophenyl)-N'- (3,4-dichlorophenyl) urea, is a polychlorinated aromatic antimicrobial that has been used in personal care products for over 60 years [1] for the prevention of spoilage and infections as it perturbs microbial fatty acid synthesis and cell membrane formation of microbes [2,3]. It belongs to the class of diarylureas (or bis-phenylureas), commonly known for their antitumor properties [4] and numerous other biological activities, and it has been recently proposed for a repositioning to antimicrobial [5] and/or for the treatment of COVID-19 [6].…”

“…TCC is added, as a preservative, into consumer products including toothpastes, baby teethers, cosmetics, household sponges, plastic cutting boards, socks and undergarments [7,8]. It is metabolized to hydroxylated species and glucuronides [2,9] and detected in human tissue such as fingernails and body fluids, including blood, urine and seminal plasma [10][11][12]. Nevertheless, given its broad use in personal care products, some concerns about its endocrine disruptive properties were raised [13].…”