Page 125 - Medicinal Chemistry Self Assessment

114 Medicinal Chemistry Self Assessment

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2. Tolterodine (Detrol ), fesoterodine (Toviaz ), and oxybutynin (Ditropan ) are anticholinergic agents
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used in the treatment of overactive bladder. Based on the structure evaluation process described in
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2. Tolterodine (Detrol ), fesoterodine (Toviaz ), and oxybutynin (Ditropan ) are anticholinergic agents
Chapter 6* and previous chapters,* “read” each of these drug molecules and determine how each
of these drug molecules interact via hydrogen bonding with the muscarinic receptor. Fill in the grid
provided with your answers.

Tolterodine Fesoterodine

Oxybutynin

Answer

Function Function
H-bond donor, One amino acid that interacts (via side

Name of H-bond chain) with the functional group via a

Functional Name of ALL Anticholinergics That acceptor, both complementary H-bonding interaction;
Group Contain Functional Group or neither NONE is a possible answer
Alkane (i.e., Tolterodine, fesoterodine, oxybutynin Neither None
alkyl chain)
Cycloalkane Oxybutynin Neither None

Aromatic hydro- Tolterodine, fesoterodine, oxybutynin Neither None
carbon
Alkyne Oxybutynin Neither None

Tertiary alcohol Oxybutynin Both Serine, threonine, cysteine, tyrosine, glutamic
acid, aspartic acid, lysine, arginine, asparagine,
glutamine, histidine, tryptophan
Primary alcohol Fesoterodine Both Serine, threonine, cysteine, tyrosine, glutamic
acid, aspartic acid, lysine, arginine, asparagine,
glutamine, histidine, tryptophan