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Halogenation of Pharmaceuticals Is an Impediment to Ready Biodegradability
For pharmacological reasons many active organic pharmaceutical substances (AOPSs) are singly or multiply halogenated. Halogenation can confer optimised steric fitting of an AOPS to its molecular receptor; moreover, by increasing the lipophilicity of a compound, passive permeation through bilipid membranes into target cells is enhanced. As halogenation is widely suspected to inhibit biodegradability in wastewater treatment plants, the relationship of halogenation vs. ready biodegradability was investigated. Among 230 AOPSs with empirical ready biodegradability data, all 70 halogenated AOPSs are not readily biodegradable, and halogenation is confirmed to be an impediment to ready biodegradability. As a counterexample to halogenation, hydrophilic substitutions (hydroxy, carboxylic-acid or terminal-amine groups) are positively correlated with ready biodegradability. Regarding halogenation, therefore, pharmacological goals stand in stark contrast to environmental goals. Possible ideas toward solutions for this contradiction are discussed.
Halogenation of Pharmaceuticals Is an Impediment to Ready Biodegradability
For pharmacological reasons many active organic pharmaceutical substances (AOPSs) are singly or multiply halogenated. Halogenation can confer optimised steric fitting of an AOPS to its molecular receptor; moreover, by increasing the lipophilicity of a compound, passive permeation through bilipid membranes into target cells is enhanced. As halogenation is widely suspected to inhibit biodegradability in wastewater treatment plants, the relationship of halogenation vs. ready biodegradability was investigated. Among 230 AOPSs with empirical ready biodegradability data, all 70 halogenated AOPSs are not readily biodegradable, and halogenation is confirmed to be an impediment to ready biodegradability. As a counterexample to halogenation, hydrophilic substitutions (hydroxy, carboxylic-acid or terminal-amine groups) are positively correlated with ready biodegradability. Regarding halogenation, therefore, pharmacological goals stand in stark contrast to environmental goals. Possible ideas toward solutions for this contradiction are discussed.
Halogenation of Pharmaceuticals Is an Impediment to Ready Biodegradability
Jürg Oliver Straub (author) / Julien Le Roux (author) / Damien Tedoldi (author)
2023
Article (Journal)
Electronic Resource
Unknown
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