Question

Based on the structures of Isoflurane & Sevoflurane and what you have learned in Modules 5 and 8 this semester, would you expect these molecules to be hydrophilic or lipophilic? Explain your answer. (Make sure you base your answer on the structures alone – please note that your answer may or may not correlate with the experimentally determined result.)

Answer 1

Both the Isoflurane and Sevoflurane are the halogenated anesthetic agents-drugs. These are the class of of inhaled anesthetic agents. They belong to the ether class of organic chemistry, specifically alkyl ether class which is broadly non-polar class of compounds..

The structures of both the drugs have been drawn as below

Isoflurane is chiral racemic drug comprising of fluorine and chlorine atoms substituted methylethyl ether (see below structure) whereas the sevoflurane has seven fluorine atoms substitted oo the methylpropyl ether (see below structure)

Based on the structural analysis and the physicochemical properties of both the drugs, it has been observed that the Isoflurane has more hydrophilic and less lophophilic character. Where as the sevoflurane is less hydrophilic and more of lipid loving character.

It is because of mainly the number of saturated carbon atoms present their structures. Sevoflurane has total four carbons and  Isoflurane has total three carbon counts which make possible that the Sevoflurane is more hydrophobic (more lipophilic) than Isoflurane (less hydrophobic, less lipophilic).

Hydrophilic character in Isoflurane is also due to the additional dipole character is induced because of C-Cl bond. The blood solubility of Sevoflurane is lower than that of Isoflurane because of Sevoflurane complete fluorination,