Page 123 - Medicinal Chemistry Self Assessment
P. 123
112 Medicinal Chemistry Self Assessment
Answer
Can this be formulated as
a. a topical ointment or cream? YES NO
b. an aqueous solution? YES NO
c. Which structural features and corresponding characteristics did you consider when answering
each of these questions?
Although there are hydrophilic functional groups that can participate in hydrogen bonding
interactions with water and impart a reasonable amount of water solubility (fluorine atoms on
the aromatic hydrocarbons, tertiary alcohol, a weakly basic nitrogen containing heterocycle [1,2,4
triazole], and oxygen containing heterocycle [1,3 dioxane]), their effect is overwhelmed by the
functional groups that are hydrophobic in character (two aromatic hydrocarbons, alkene, thio-
ether). This hydrophobic character allows for good drug penetration into and across the skin if
applied as a topical cream or ointment; however, this character is likely to significantly limit the
drug’s water solubility as an aqueous solution.
Go to Section 1.5 [Link to section 1.5 title]
Note: References to chapters are to Chapter 5 in Harrold MW and Zavod RM, Basic Concepts in Medicinal
Chemistry, American Society of Health-System Pharmacists, ©2013.
