Percutaneous absorption and metabolism of Irgasan® DP300

Black, J.G.; Howes, D.; Rutherford, T. R.

doi:10.1016/0300-483x(75)90006-2

Cited by 62 publications

(35 citation statements)

References 7 publications

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“…Unchanged triclosan and triclosan glucuronide were identified in urine and feces, with small amounts of triclosan sulfate in urine (Moss et al, 2000). In an earlier study, rats and guinea pigs treated with 1% triclosan in a soap formulation to the skin excreted triclosan glucuronide as the major urinary metabolite (Black et al, 1975).…”

Section: Discussionmentioning

confidence: 99%

“…As a hydroxylated compound, it should be expected that glucuronidation and sulfonation would be the main pathways of triclosan metabolism. One study showed that triclosan was excreted primarily as the glucuronide following application of a 1% formulation to guinea pig or rat skin (Black et al, 1975). Another study showed that topically applied triclosan formed sulfate and glucuronide conjugates in human as well as rat skin (Moss et al, 2000).…”

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confidence: 99%

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Triclosan as a Substrate and Inhibitor of 3′-Phosphoadenosine 5′-Phosphosulfate-Sulfotransferase and Udp-Glucuronosyl Transferase in Human Liver Fractions

Wang

Falany

James³

2004

Drug Metab Dispos

172

140

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ABSTRACT:Triclosan is a broad spectrum antibacterial agent used in many household products. Due to its structural similarity to polychlorobiphenylols, which are potent inhibitors of the sulfonation and glucuronidation of 3-hydroxy-benzo[a]pyrene, it was hypothesized that triclosan would inhibit these phase II enzymes. This study was designed to assess the interactions of triclosan as a substrate and inhibitor of 3-phosphoadenosine 5-phosphosulfate-sulfotransferases and UDP-glucuronosyltransferases in human liver cytosol and microsomes.

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

Triclosan as a Substrate and Inhibitor of 3′-Phosphoadenosine 5′-Phosphosulfate-Sulfotransferase and Udp-Glucuronosyl Transferase in Human Liver Fractions

Wang

Falany

James³

2004

Drug Metab Dispos

172

140

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“…Though some reports on the transformation of halogenated diphenyl ether compounds by bacteria are available (21,30), triclosan itself was not metabolized by the strains tested (31) or by Rhodococcus chlorophenolicus, which can methylate several other chlorinated hydroxydiphenyl ethers (34). Several hydroxylated metabolites, as well as 2,4-dichlorophenol and 4-chlorocatechol, are formed from triclosan by rats (33), while guinea pigs mostly form glucuronide conjugates (3). No reports exist concerning the degradation of triclosan by fungi.…”

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confidence: 99%

Transformation of Triclosan by Trametes versicolor and Pycnoporus cinnabarinus

Hundt

Martin

Hammer

et al. 2000

Appl Environ Microbiol

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We investigated the ability of Trametes versicolor and Pycnoporous cinnabarinus to metabolize triclosan. T. versicolor produced three metabolites, 2-O-(2,4,4-trichlorodiphenyl ether)-␤-D-xylopyranoside, 2-O-(2,4,4-trichlorodiphenyl ether)-␤-D-glucopyranoside, and 2,4-dichlorophenol. P. cinnabarinus converted triclosan to 2,4,4-trichloro-2-methoxydiphenyl ether and the glucoside conjugate known from T. versicolor. The conjugates showed a distinctly lower cytotoxic and microbicidal activity than triclosan did.Triclosan (2,4,4Ј-trichloro-2Ј-hydroxydiphenyl ether; synonym, Irgasan DP 300) has been used as an antimicrobial compound in deodorants (6), soaps, and dentifrices (2, 8, 36) for many years. The mode of action of triclosan has, however, remained unclear. Recently, it was shown that triclosan blocks one step in bacterial fatty acid synthesis (20,24,25). Due to its widespread use, triclosan and some of its derivatives can be detected in the environment (22,26,27). The chemical structure of triclosan is related to many compounds which are wellknown as xenobiotics, such as halogenated diphenyl ethers. Though some reports on the transformation of halogenated diphenyl ether compounds by bacteria are available (21, 30), triclosan itself was not metabolized by the strains tested (31) or by Rhodococcus chlorophenolicus, which can methylate several other chlorinated hydroxydiphenyl ethers (34). Several hydroxylated metabolites, as well as 2,4-dichlorophenol and 4-chlorocatechol, are formed from triclosan by rats (33), while guinea pigs mostly form glucuronide conjugates (3). No reports exist concerning the degradation of triclosan by fungi. The white rot fungi Trametes versicolor and Pycnoporus cinnabarinus are capable of transforming diphenyl ethers, like 4-chlorodiphenyl ether, up to ring cleavage (10, 11). Hydroxylated biarylic ethers are transformed to oligomerization products by laccases secreted by these strains (13). In this paper we describe some biotransformation reactions of triclosan by the white rot fungi T. versicolor and P. cinnabarinus.The strains T. versicolor SBUG-M 1050, T. versicolor DSM 11269, T. versicolor DSM 11309, and P. cinnabarinus SBUG-M 1044 were cultivated in a nitrogen-rich (8 mM) medium. The cultures for transformation were prepared with 0.25 mM (wt/ vol) triclosan (Mallinckrodt-Baker, Griesheim, Germany) and inoculated and incubated as described previously (10, 11).Cell extracts were prepared from a 3-day culture of T. versicolor, harvested by centrifugation, and washed twice with 50 mM ice-cold Tris-HCl buffer (pH 7.5). Cells were broken at 1,000 lb/in 2 using a French press (SLM Amnico, Rochester, N.Y.) and were immediately resuspended in Tris-HCl buffer. The cell extracts (4 ml, approximately 5 mg of protein ml Ϫ1 ) were incubated at 30°C for 24 h with 2.88 mg of triclosan and 1 mg each of UDP-xylose, UDP-glucose, and UDP-glucuronic acid (Sigma, Deisenhofen, Germany).Analysis of metabolites in culture supernatants and purification of intermediates were done by high-performance liquid ...

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“…Radiolabeled triclosan was used to study its percutaneous absorption and metabolic fate in humans and animals (1). A GLC technique quantitatively determined free and conjugated triclosan in whole blood without an internal standard (2).…”

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confidence: 99%