32 Questions
Which group shift prevents the action of COMT enzyme in the context of β2-agonist discovery?
Shifting the OH group from para position to meta position
What is the fundamental pharmacophore for all β-adrenergic agonists?
Substituted β-phenylethanolamine
What confers both β1- and β2-receptor selectivity in β-adrenergic agonists?
The bulk of the N-substituent (R1)
What prevents action by Ndealkylation in the metabolism of β2-agonists?
Addition of a tertiary butyl group
What makes a compound unrecognizable by the metabolic enzyme while still binding to the receptor site in the context of β2-agonist discovery?
Presence of an m-OH group (R2)
What role do direct-acting β-agonists play in binding to the receptor site?
They bind to the receptor similar to EPI
Which medication has a bitopic structure and is resistant to both MAO and COMT enzymes?
Salmetrol
What is the main reason for the long duration of action of Formoterol?
Association with lipid bilayer
Which leukotriene antagonist is contraindicated in liver impairment?
Zafirlukast
Which leukotriene antagonist has a FDA caution for the risk of neuropsychiatric events?
Montelukast
Which medication is an injectable prescription medicine used to treat moderate to severe allergic asthma?
XOLAIR® (omalizumab)
Which medication is highly lipophilic with optimal direct-acting β2-receptor selectivity and potency?
Salmetrol
Which medication has a lipophilic β-directing N-isopropyl p-methoxyphenyl group on the nitrogen atom?
Formoterol
Which medication is associated with drug-drug interactions with other drugs metabolized by CYP3A4?
Zafirlukast
What makes Tiotropium bromide more cost-effective compared to Ipratropium in the treatment of COPD?
Given once compared to three to four times daily
Which medication has a lipophilic substituent in combination with a βOH group and a salicyl phenyl ring?
Formoterol
What is the fundamental pharmacophore for all β-adrenergic agonists?
Substituted β-phenylethanolamine
What is the main reason for the long duration of action of Formoterol?
Resistance to MAO and COMT enzymes
Which medication has a lipophilic substituent in combination with a βOH group and a salicyl phenyl ring?
Formoterol
What confers both β1- and β2-receptor selectivity in β-adrenergic agonists?
Bulk of the N-substituent (R1)
What makes a compound unrecognizable by the metabolic enzyme while still binding to the receptor site in the context of β2-agonist discovery?
Shift of the OH group to the meta position
What prevents action by Ndealkylation in the metabolism of β2-agonists?
Tertiary butyl groups
What is the primary reason behind the long duration of action of Tiotropium bromide?
Association with lipid bilayer
Which medication is hepatically metabolized by CYP2C9 and inhibits the action of CYP3A4, leading to drug-drug interactions with other drugs metabolized by CYP3A4?
Zafirlukast
Which leukotriene antagonist is contraindicated in liver impairment?
Zafirlukast
What is the role of LABAs such as Salmetrol in terms of receptor selectivity and potency?
Highly lipophilic with optimal selectivity and potency
Which medication is an orally administered leukotriene receptor antagonist used for the prophylaxis and chronic treatment of asthma in adults and children 5 years of age and older?
Zafirlukast
What makes XOLAIR® (omalizumab) unique in its use for treating allergic asthma?
Injectable monoclonal antibody/IgE binding inhibitor
Which medication has a lipophilic β-directing N-isopropyl p-methoxyphenyl group on the nitrogen atom?
Formotero l
What is the pharmacokinetic advantage of using Tiotropium bromide over Ipratropium in cases of COPD treatment?
Cost-effectiveness due to less frequent administration
What is the fundamental pharmacophore for all β-adrenergic agonists?
Salicyl phenyl ring for optimal direct-acting β2-receptor selectivity and potency
What confers both β1- and β2-receptor selectivity in β-adrenergic agonists?
Presence of 3’-formylamino (β-directing) group
Study Notes
β2-Agonist Discovery
- The para-hydroxyl group shift prevents the action of COMT enzyme in the context of β2-agonist discovery.
- The fundamental pharmacophore for all β-adrenergic agonists is a β-phenethylamine structure.
- A lipophilic substituent on the nitrogen atom confers both β1- and β2-receptor selectivity in β-adrenergic agonists.
- A βOH group prevents action by Ndealkylation in the metabolism of β2-agonists.
- A lipophilic substituent on the nitrogen atom makes a compound unrecognizable by the metabolic enzyme while still binding to the receptor site.
Medications
- Salmeterol has a bitopic structure and is resistant to both MAO and COMT enzymes.
- The main reason for the long duration of action of Formoterol is its high lipophilicity.
- Zafirlukast is contraindicated in liver impairment.
- Montelukast has a FDA caution for the risk of neuropsychiatric events.
- Omalizumab is an injectable prescription medicine used to treat moderate to severe allergic asthma.
- Formoterol is highly lipophilic with optimal direct-acting β2-receptor selectivity and potency.
- Salmeterol has a lipophilic β-directing N-isopropyl p-methoxyphenyl group on the nitrogen atom.
- Montelukast is associated with drug-drug interactions with other drugs metabolized by CYP3A4.
COPD Treatment
- Tiotropium bromide is more cost-effective compared to Ipratropium in the treatment of COPD due to its longer duration of action.
- Tiotropium bromide has a lipophilic substituent in combination with a βOH group and a salicyl phenyl ring.
- The primary reason behind the long duration of action of Tiotropium bromide is its high lipophilicity.
- The pharmacokinetic advantage of using Tiotropium bromide over Ipratropium in cases of COPD treatment is its longer duration of action.
Leukotriene Antagonists
- Zafirlukast is an orally administered leukotriene receptor antagonist used for the prophylaxis and chronic treatment of asthma in adults and children 5 years of age and older.
- XOLAIR (omalizumab) is unique in its use for treating allergic asthma as it is an injectable prescription medicine.
Test your knowledge of the discovery and mechanism of β2-agonists in the context of respiratory system issues. This quiz covers the storyline of β2-agonist discovery and its application in medicinal PD511, Fall Semester 2023/2024.
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