Pharmaceutical Organic and Medicinal Chemistry

1. Which of the following is/are true regarding alcohols?

i. Antibacterial potency of primary alcohols against S. aureus increases with MW up to 3 carbons only

ii. Branching increases potency

iii. Example of alcohol include Spiritus vini rectificatus

• I

• II

• III

• I, II, III

Answer explanation

Antibacterial potency increases with MW up to C8

Branching decreases potency

Spiritus vini rectificatus – aka: Alcohol, USP; wine spirit; ethanol

The following are physiologic factors involving drug metabolism, except:

• Deficient microsomal enzymes in infants especially in glucuronide conjugation

• Increase in drug metabolism in the elderlies

• Gender differences such as in propranolol which is 50% faster in males than in females

• Oxidative metabolism of drugs are more rapid in males

Answer explanation

There is a decrease in drug metabolism in elderlies due to decrease in hepatic blood flow, glomerular filtration rate, hepatic microsomal enzyme activity, plasma protein binding, and body mass resulting to profound changes in drug plasma concentration.

Norepinephrine's R1 and R2 are both H, its receptor activity is said to be at alpha and beta receptors. What is the substituent at the R3 position?

• 3',4'-diOH

• 3'-OH

• 2',5'-diOCH3

• H

Answer explanation

The natural 3′,4′-dihydroxy–substituted benzene ring in norepinephrine provides excellent receptor activity for both α- and β-sites. Such catechol-containing compounds have poor oral activity, however, because they are rapidly metabolized by COMT.

Remember: catechol is benzenediol

Phenothiazine and the thioxanthene derivatives used as neuroleptics has the general structure as the one seen above. Which of the following has an R2 substituent of SCH3 with a trade name of Mellaril?

• Chlorpromazine HCl

• Thioridazine HCl

• Mesoridazine mesylate

• Perphenazine

Answer explanation

Which of the following is/are true regarding barbiturates?

1. Binds to GABAA receptors

2. Barbituric acid is the pharmacophore from which all barbiturates are derived

3. Unbranched saturated groups at C5 produce barbiturates with a shorter onset of action and decreased duration of action

4. Both H atoms on C5 must be replaced for maximal activity

• I, II, III

• I, II, IV

• II, III, IV

• I, III, IV

Answer explanation

Branched, cyclic, or unsaturated groups at C5 produce barbiturates with a shorter onset of action and decreased duration of action

Which of the following structures describes Methoxyflurane?

• 
• 
• 
• 

Answer explanation

Enflurane

Halothane

Isoflurane

Which of the following brands is an example of a selective norepinephrine reuptake inhibitor (SNRI)?

• Strattera

• Celexa

• Zoloft

• Silenar

Answer explanation

Strattera - Atomoxetine

Celexa - Citalopram (SSRI)

Zoloft - Sertraline (SSRI)

Silenar - Doxepin (NSRI)

Which of the following is/are not true regarding the SAR of Quinolones?

• R1 is not important for potency

• R1 is commonly consists of an ethyl or cyclopropyl substituent

• R8 affects spectrum of activity as does R1/R8 linked forming a third ring in the moelcule

• R1 is important for potency

Answer explanation

R1 is important for potency

The above structure is also known as?

• cyclic ketone

• cyclic amide

• cyclic ester

• cyclic amine

Answer explanation

the structure is also known as the beta-lactam ring.

Amine vs Amide?

Amide contains carbonyl group, while amine doesn't.

This was approved in 2010 and currently unique among the marketed β-lactams because of its affinity to “abnormal” PBPs.

• Ceftaroline fosamil

• Cefepime

• Cefditoren pivoxil

• Cefdinir