Lecture 13 - Beta Adrenergic Agonists

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4 Terms

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SAR for beta 2 agonist activity

  1. Amino substituent Needs to be larger than methyl. A bulky branched alkyl substituent is essential for beta activity [e.g., isopropyl (B1 =B2), t-butyl B2>B1]

  2. Basic nitrogen atom (ionized (protonated) form interacts with receptor)

  3. alpha-carbon substitution —> An ethyl substituent increases beta-selectivity by diminishing binding to the alpha-receptor. (Substituent larger than ethyl results in loss of binding from beta receptor.)

  4. beta-OH group Essential for overall direct agonist activity; important for H-bonding (Needs to be in the R-configuration. Does not play a role in beta vs alpha selectivity)

  5. Aromatic ring substituents: Catechol is essential but produces limited bioavailability due to chemical (orthoquinone formation) and metabolic instability (COMT), so Catechol modifications improve stability while still retaining activity.

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Phenethanolamine Derivatives list

short acting beta 2 (SABAs), long acting beta 2 (LABAs), ultra long acting beta 2

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long and ultra long acting SAR difference

big hydrophobic group attached to amine increases B2 receptor selectivity/affinity and DOA

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B1 agonist SAR

  1. Phenethylamine

  2. as a catechol and a primary amine, dopamine is rapidly metabolized by COMT and MAO, has a short duration of action with no oral activity.

  3. Some beta1 agonist activity

  4. NO beta OH (decreases direct action)

  5. ionizable amine