Page 72 - Medicinal Chemistry Self Assessment

1.17 and 2.17 – remove bold from label

E

C

F
B

D
A
Section 2 Whole Molecule Drug Evaluation
Hydrocortisone

Question #3 structure needs to be replaced:
1.18 Levothyroxine (T )
4

21
17
11
Levothyroxine (T ) is a naturally produced thyroid pro-hormone. In its active form, tri-iodo-L-thyronine (T ) is
3
4
responsible for regulating oxygen consumption and calorigenesis (think metabolism, metabolic rate, and thermogen-
A
esis). T is biosynthesized and stored in thyroglobulin molecules until it is needed. Once proteolyzed from thyroglob-
4
ulin and transported to the desired target tissue, T undergoes dehalogenation catalyzed by thyroxine dehalogenase to
4
the active thyroid hormone T .
3

1. Conduct a structural evaluation of T , focusing on the boxed functional groups, and use the information in
1.18 and 2.18 – remove bold from label
4
the grid to inform your answers to the questions that follow.

E
A I C D O
H O I
OH
NH
I O 2
B I

L-Thyroxine

Function
Amino Acids That
Character Function Can Interact with
Acidic, Basic, Interaction(s) the Functional
Character or Neutral Function Possible with Group via Hydrogen

Name of Hydrophilic Provide ↑ Solubility Biological Target Bonding Interactions
Functional and/or pK When and/or at Physiological at pH=7.4
a
Group Hydrophobic Relevant ↑ Absorption pH=7.4 None Is Acceptable
A
B
C
D
E

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