Page 175 - Medicinal Chemistry Self Assessment

4. In its active form, dabigatran mimics the D-Phe-Pro-Arg tripeptide chains.
O
NH
3
H
N
N
2
O
H
N
O
H
1
N
H
2
2
N
D-Phe-Pro-Arg Tripeptide Sequence R

5. Review side chain indicated.
164 Medicinal Chemistry Self Assessment

A B E F
Answer
O O D H NH 2
D-Phe mimic Pro mimic Arg mimic N
N
A No H O No N No NH
B No No No N
N
C Yes Yes C No CH 3
D Yes Yes No
E Yes Yes No
F No No Yes
Active form of Dabigatran

6. Dabigatran etexilate is formulated as a mesylate salt. Provide a brief rationale for the value of
administering the salt form of a drug.
6. Dabigatran salt. Provide a brief rationale for the value of administering the salt form of a drug.

Dabigatran etexilate mesylate
Dabigatran etexilate mesylate
Answer
Mesylate salts are considered water soluble organic salts. The use of water soluble organic salts is
one method to enhance the overall water solubility of your drug. This is accomplished by increased
solvation and dissolution of the drug. The use of a water soluble organic salt also helps to ensure an
adequate water/lipid balance necessary for oral absorption. As we have already determined in the
structure evaluation grid, there is some hydrophobic character present, but there is also substantial
hydrophilic character.

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