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WorksheetsPODA 3 Exam 2 Med Chem
Total questions: 30
Worksheet time: 19mins
WOTF staements about erythromycin is/are correct?
Erythromycin binds with bacterial 50s ribosomes and interacts with the 23s ribosomal RNA
Erythromycin contains 14 membered lactone ring
Erythromycin contains cladinose and desoamine
Select the correct order of water solubility of the erythromycin salts
3>2>1
3>1>2
1>2>3
2>1>3
WOTF erythromycin salt is water insoluble and used via oral route?
1
2
3
WOTF is water soluble and used for parenteral (IV) admin ?
1
2
3
Erythromycin contains
14 membered lactam ring with 10 chiral centers
13 membered lactam ring with 10 chiral centers
10 membered lactone ring with 10 chiral centers
14 membered lactone ring with 10 chiral centers
WOTF about azithromycin is/are correct?
Azithromycin is very unstable becasue of rapid acid catalyzed internal cyclic ketal formation
Azithromycin has 15 membered lactone ring
In azithromycin the carbonyl moiety is absent and does not form a cyclic ketal
Tetracycline can lose ~ half its potency by the following chemical reaction
Oxidation
Dehydration
Reduction
Epimerization
When exposed to dilute conditions, tetracyclines unfergo ___ to yield inactive anhydrotetracycline
Oxidation
Dehydration
Epimerization
Reduction
When exposed to dilute acid conditons: WOTF tetracyclines undergo dehydration to yield inactive anhydrotetracycline?
1
2
3
WOTF statements about tetracycline degredation products is/are false?
Epitetracycline is inactive and toxic
Anhydrotetracycline is inactive and toxic
Epianhydrotetracycline is inactive and toxic
WOTF statements about tetracycline is/are correct?
Alpha-stereo orientation of the C-4 dimethylamino moiety of the tetracycline is essential for pharmacological activity
Beta-stereo orientation of the C-4 dimethylamino moiety of the tetracyclines is essential for pharmacological activity
Beta-steroa orientation is more active thatn alpha-stereo orientation
Tetracycline, chlortetracycline and oxytetracycline form insoluble complexes with
Mg 2+
Ca 2+
Fe 2+
WOTF tetracycline is more lipid soluble and have very high bioavailablity?
1
2
3
WOTF is/are correct?
Epitetracycline is inactive
Epianhydrtetracycline is toxic
Anhydrotetracycline is inactive
WOTF about azithromycin is/are correct?
In azithromycin the carbonyl moiety is absent and does not form a cyclic ketal
Azithromycin binds with bacterial 50s ribosomes and interacts with the 23s ribosomal subunit
Azithromycin is very unstable becasue of rapid acid catalyzed internal cyclic ketal formation
WOTF statements is/are correct?
Southern and Northern sides interact with eRNA
Tetracycline binds with bacterial 30s ribosomes and interact with the 16s ribosoamal RNA
Tetracyclines are amphoteric
Southern and Eastern sides interaact with rRNA
Tetracycline binds with bacterial 50s ribosomes and interacts with 23s ribosomal RNA
t
WOTF about clarithromycin is/are correct?
Clarithromycin is a 14 member lactone ring
Clarithromycin is a 15 member lactone ring
In clarithromycin C-6 hydroxy group has been converted to a methyl ether and does not form a cyclic ketal
Clarithromycin is a 14 member lactam ring
Clarithromycin binds with bacterial 50s ribosomes and interaacts with the 23s ribosomal RNA
WOTF statements about sulfisoxazole/sulfamethoxizole is/are correct?
Sulfosoxazole is predominaantly unionized at physiological pH
Sulfisoxazole is predominanatly ionized at physiological pH
Sulfamethoxazole is a negatively charged molecule at physiological pH
Sulfisoxazole is positively charged at pysiological pH
Sulfamethoxazole is neutral at physiological pH
WOTF statements about sulfisoxazole/sulfamethoxizole is/are correct?
Sulfisoxazole is a structureal analog of GABA
Sulfamethoxazole is is a structural analog of para-aminobenzoic acid
Sulfisoxazole inhibits dihydrofolate synthase
Sulfonamides are metabolized and deactivated by glucoronide conjugation
Sulfonamides are metabolized and deactivated by acetylation
WOTF statements is true about the follwoing structure (Sulfasalazine)
It is a prodrug with is converted to prontosil in the body
It is a prodrug which is converted to sulfapyridine and 5-aminosalicyclic acid int he body
It is a prdrug which is converted to sulfapyridine and aspirin in the body
It is a prodrug which is converted to trimethoprim and sulfamethoazole in the body
What is the target for the antibacterial trimethoprim?
Inhibit dihydropterate synthase
Activates Dihydrofolate reuctase
Inhibits Dihydrofolate reductase
Inhibits tetrahydrofolate reductase
Which region of the fluoroquinolone skeleton is nvolved in binding witht he DNA/DNA-gyrase enzyme system?
A
B
C
D
WOTF statements about Fluoroquinolones isare correct?
Cipro has higher oral bioavialbilty than Levofloxacin and norfloxcacin
Cipro is a prodrug that is converted to ofloxacilin
Avelox has the higher oral bioavailability than Cipro and Levaquin
Avelox has the higher bioavailability than Cipro and Norfloxacin
WOTF statements about Fluoroquinolones is/are correct?
Fluoroquinolones are a weak base
Levaquin has the higher oral bioavailability than Cipro and Norfloxacin
Cipro and Norfloxacin have a shorter duration of action and requires a more frequent dosing interval
Ofloxacin and Norfloxacin have a shorter duration of action and require a more frequent dosing interval
WOTF statements about Fluoroquinolones is/are correct?
Fluoroquinolones are weak acids
Norfloxacin has the lowest oral bioavailability
Cipro has a longer duration of action
Avelox has a longer duration of action
Select the correct statement(s)
The addition of a fluoro group to the 6 position of the quinolones
Decreases lipophilicity
Decreases hydrophilicity
Increases bacterial cell wall penetration
Increases Lipophilicity
Select the correct statement(s)
Fluoro group at C-8 improves drug absorption
Fluoro group at C-8 improves half life
Substitution of a methoxy group at C-8 reduces photosensitivty
Fluoro group at C-8 reduces half life
Select the correct statement(s)
Involving the Quinolone C-7 location
Heterocyclic substitution improves spectrum of activity
A piperazinyl group at C-7 increase CNS side effects
Alkyl substitution on the piperazine Nitrogen increase GABA binding
Alkyl substitution on the piperazine Nitrogen decrease GABA binding
FITB: he cyclopropyl substitution at N-1 appears to ____ activity of the quinolones to include activity against ____ bacteria including Mycoplasma, Chlamydia, and Legionella species.
decrease: atypicals
Increase : atypicals
decrease: anaerobes
increase: anaerobes
WOTF statements about clarithromycin is/are correct?
In clarithromycin C-6 hydroxy group has been converted to a methyl ether
In clarithromycin methyl ehter prevents internal ketal formation
clarithromycin is more hydrophilic than erythromycin
