F. Vacondio, Claudia Silva, M. Mor
Sep 29, 2010
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Influential Citations
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Quality indicators
Journal
Drug Metabolism Reviews
Abstract
The aims of this review were 1) to compile a large number of reliable literature data on the metabolic hydrolysis of medicinal carbamates and 2) to extract from such data a qualitative relation between molecular structure and lability to metabolic hydrolysis. The compounds were classified according to the nature of their substituents (R3OCONR1R2), and a metabolic lability score was calculated for each class. A trend emerged, such that the metabolic lability of carbamates decreased (i.e., their metabolic stability increased), in the following series: Aryl-OCO-NHAlkyl >> Alkyl-OCO-NHAlkyl ∼ Alkyl-OCO-N(Alkyl)2 ≥ Alkyl-OCO-N(endocyclic) ≥ Aryl-OCO-N(Alkyl)2 ∼ Aryl-OCO-N(endocyclic) ≥ Alkyl-OCO-NHAryl ∼ Alkyl-OCO-NHAcyl >> Alkyl-OCO-NH2 > Cyclic carbamates. This trend should prove useful in the design of carbamates as drugs or prodrugs.