A newly discovered xenobiotic metabolic pathway: Ethyl ester formation

Chou, Ruby C.; Wyss, R.; Huselton, Christine; Wiegand, U.

doi:10.1016/0024-3205(91)90332-6

Cited by 22 publications

(20 citation statements)

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“…The formation of etretinate, after addition of ethanol to acitretin. was demonstrated in in vitro studies using liver homogenates [30] or hepatocytes in culture [31 ] from animals and humans. This ethylesterification was also shown in vivo both in rats [30] and in human volunteers who received an oral dose of acitretin with con comitant ethanol ingestion [32].…”

Section: Isomerization and Esterification O F Acitretinmentioning

confidence: 99%

“…was demonstrated in in vitro studies using liver homogenates [30] or hepatocytes in culture [31 ] from animals and humans. This ethylesterification was also shown in vivo both in rats [30] and in human volunteers who received an oral dose of acitretin with con comitant ethanol ingestion [32]. It is notable that the etreti nate levels measured in plasma during acitretin treatment in humans are by far lower than those measured after etreti nate treatment.…”

Section: Isomerization and Esterification O F Acitretinmentioning

confidence: 99%

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Teratogenic Risk with Etretinate and Acitretin Treatment

1994

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Etretinate (Tigason®, Tegison®) and its active metabolite acitretin (Neotigason®, Soriatane®) are known teratogens. Pregnancy should be avoided during treatment and until 2 years after treatment discontinuation. The question is discussed whether a dose or a blood concentration of the drug below which there is no teratogenic risk can be determined. Animal experimental and human pharmacokinetic data are reviewed. An evaluation of the outcomes of pregnancies which occurred in mothers exposed to etretinate or acitretin was performed. A threshold dose in human therapy below which there is no risk of congenital malformation cannot be determined based on animal experimental data. With regard to pharmacokinetics, there are currently no data suggesting that blood levels of the drug below the detection limit of 2 ng/ml are associated with a teratogenic risk. The most useful information is given by reports in women who were exposed to either retinoid before or during pregnancy. The data indicate that the risk of spontaneous abortion or congenital malformation is high when the drug is administered during the first trimester of pregnancy. After treatment discontinuation, the risk is low since the number of abnormalities seems not to exceed those observed in a general population. There are currently no available data which suggest that the pregnancy warnings are inappropriate in terms of duration of contraception.

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Section: Isomerization and Esterification O F Acitretinmentioning

confidence: 99%

Section: Isomerization and Esterification O F Acitretinmentioning

confidence: 99%

Teratogenic Risk with Etretinate and Acitretin Treatment

1994

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“…26 Although the mechanism is obscure, alcohol intake has been suggested as an important contributory factor.2' Those taking acitre¬ tin with a predilection for conversion are likely to display plasma etretinate levels. The clinical relevance of this ob¬ servation relates to the high teratogenic potential of the retinoids, which is already a preeminent consideration in pa¬ tient selection.…”

Section: Methodsmentioning

confidence: 99%

Acitretin Therapy Is Effective for Psoriasis Associated With Human Immunodeficiency Virus Infection

Buccheri

Katchen²,

Karter³

et al. 1997

Arch Dermatol

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“…Other retinoids like acitretin 8,9 and all‐ trans ‐retinoic acid 10 containing a carboxylic acid moiety are capable of undergoing an ethyl esterification with the metabolic formation of more lipophilic compounds with much longer terminal elimination half‐lives than the parent drug. In vitro studies in both rat and human liver supernatants have demonstrated that ethanol enhances but does not seem to be essential for the metabolic reaction 11,12 . This is the first pharmacokinetic study with the aim of determining whether isotretinoin, its main metabolite 4‐oxo‐isotretinoin and other possible metabolites including all‐ trans ‐retinoic acid in the presence or absence of ethanol are converted to their corresponding ethyl derivatives in severe acne and rosacea during long‐term isotretinoin therapy.…”

mentioning

confidence: 99%