Page 188 - Medicinal Chemistry Self Assessment

Section 4 Whole Molecule Drug Evaluation

Answers

2.17 Hydrocortisone

Hydrocortisone is a glucocorticoid used in the management of inflammation. Derivatives of hydrocortisone are used
in the management of asthma and chronic obstructive pulmonary disease.

1.17 and 2.17 – remove bold from label
1. Conduct a complete structural evaluation of hydrocortisone and use the information in the grid to inform

your answers to the questions that follow.

E

C

F
B

A D

Hydrocortisone

Answer
Question #3 structure needs to be replaced:
Function
Function
Character Amino Acids That
Interaction(s) Can Interact with
Acidic, Basic, the Functional
Character or Neutral Function 21 Possible with Group via Ion–
Biological
17
Name of Hydrophilic Provide 11 ↑ Solubility Target Dipole 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
A Ketone Hydrophilic (CO) Neutral Solubility (CO) H-bonding (A) Lys, Arg, Glu, Asp

Hydrophobic (R) Absorption (R) Dipole–dipole

Ion–dipole (as the
dipole)
Neutral
Absorption
Hydrophobic
B Cycloalkene Hydrophobic 1.18 and 2.18 – remove bold from label None
van der Waals

C Secondary Hydrophilic (OH) Neutral Solubility (OH) H-bonding (A+D) Lys, Arg, Glu, Asp
E
alcohol Hydrophobic (R) Absorption (R) Dipole–dipole
O
A I C D Ion–dipole (as the
H O I dipole)
OH
NH
I O 2
B 177 I
L-Thyroxine