MEDICINAL CHEMISTRY II EXAM #2 April 1, 2005

Transcription

1 MEDIIAL EMITRY II EXAM #2 April 1, 2005 ame Med. hem umber ETI A. Answer each question in this section by writing the letter corresponding to the best answer on the line provided (2 points each; 50 points total) 1. The drug illustrated below: l 2 2 I Is a benzoate ester local anesthetic II annot penetrate into neurons because it is 100% charged at all p values III Is used as a topical local anesthetic on mucous membranes and is sold over the counter 2. The drug illustrated below is: I II III an be addicting Is a µ-agonist Is used to treat pain 3. The drug illustrated below: 2 l 2 I an reverse respiratory depression resulting from an overdose of opioid narcotics II Is most effective when given orally III Is a potent µ-agonist

2 4. The drug illustrated below: I Is an analog of PGE 1 II Is used to prevent gastric ulcers in patients 2 III Is an analog of PGF 1α 2 5. The drug illustrated below: I Is a pro-drug that must be metabolized to 3 a sulfone to become active as an antiinflammatory agent II Inhibits cyclooxygenases after being F 2 2 metabolized to its active form III Is a pro-drug that must be metabolized to a sulfide to become active as an antiinflammatory agent 6. The drug illustrated below: I Is used to treat chronic gout II Is a uricosuric agent III Inhibits the migration of granulocytes into the area of inflammation during an acute gout attack

3 7. The drug illustrated below: 2 I Is highly psychologically-addicting II Is a benzoate ester local anesthetic III Is completely uncharged at p The drug illustrated below: I as little or no antitussive activity II Is orally active 3 III Is used to treat pain l 9. The drug illustrated below: Br I Is a µ-agonist II auses pain because it is an enantiomer of the normal morphinan ring system III Is used over the counter to treat coughs

4 10. The drug illustrated below: I electively inhibits X-II 2 II Is used primarily to treat ear ache pain III Is used as a uricosuric agent The drug illustrated below: 3 I Is used as an antiinflammatory agent to treat arthritis II an cause liver damage when taken in excessive dosages III Reduces fever and relieves pain 12. The drug illustrated below: I II 3 III 3 Is useful at high doses in treating cyanide poisoning Is useful at low doses in treating methemoglobinemia Is 100% charged at all p values l The drug illustrated below: I Is used mainly in over the counter 2 2 treatments for diarrhea II Is a salt of citric acid III Is a potent µ-agonist

5 14. The drug illustrated below: l I Is used, together with atropine to treat diarrhea II Is metabolized by hydrolysis to a compound that is also used as an antidiarrheal III an become addicting The drug illustrated below: 2 I Is metabolized to salicylic acid, an antiinflammatory agent II Is an antiinflammatory agent III Irreversibly inhibits X in human platelets 16. The drug illustrated below: 3 I II III Is a selective X II inhibitor Is an imidazoline derivative Is used to treat ear ache pain 17. The drug illustrated below: 2 l I Is used, together with epinephrine, as a local anesthetic during dental procedures II Is deactivated by hydrolysis of the ester group III hould be stored in vials under nitrogen to avoid environmental oxidation of the aromatic amine

6 18. The drug illustrated below: I Is a µ-antagonist II Is used for the controlled withdrawal of addicts from opioid dependence III Is a µ-agonist The drug illustrated below: 2 I Is used to treat pain II Is a partial µ agonist III Belongs to the lidocaine class of local anesthetics 20. The drug illustrated below: 2 a I Is metabolized in the colon to two molecules of salicylic acid II Works by inhibiting cyclooxygenase in the colon III Is metabolized in the colon to two a 2 molecules of 5-aminosalicylic acid 21. The drug illustrated below: F I Is useful for reducing fever II Is metabolized to salicylic acid F 2 III an be used to treat arthritis

7 22. The drug illustrated below: I Is a potent µ-agonist 2 II Is an agonist at κ-receptors and an antagonist at µ- l receptors III Is used to treat pain with a lower likelihood of causing respiratory depression The drug illustrated below: 3 2 I Is a preferred drug for analgesia during labor II as a relatively short duration of action because of rapid hydrolysis of the ester group III Behaves as an agonist for both the µ- and κ- receptors 24. The drug illustrated below: I Inhibits the synthesis of prostaglandins in the eyes II Is used in the eyes to prevent surgically induced miosis during 2 cataract surgery III an be metabolized to a secondary alcohol

8 25. The drug illustrated below: 2 2 I II III Is used to treat acute attacks of gout Facilitates the excretion of excess uric acid Is used to treat chronic gout 8 ection B. For each of the following answer the questions pertaining to the metabolism of the drugs shown in the boxes. You will be awarded 1 point for each correct metabolite and will lose 1 point for each incorrect metabolite. (10 Points). 1. n the line, write the letter(s) corresponding to all likely phase I metabolic pathways for the drug shown in the box below. A B D 2 F E

9 9 2. n the line, write the letter(s) corresponding to all likely phase I metabolic pathways for the drug shown in the box below. B A D F E

10 3. n the line, write the letter(s) corresponding to all likely phase I metabolic pathways for the drug shown in the box below A B D E

11 11 ection. n the line to the right of each of the following structures write the letter corresponding to its generic name (shown at bottom of page). (10 Points) P 4 l l A. Butamben Picrate B. Lidocaine. Morphine Phosphate D. Ibuprofen E. Pentazocin F. Benzocaine G. Probenecid. odeine Phosphate I. Loperamide J. alsalate K. almefene ydrochloride L. ydrocodone ydrochloride M. Rofecoxib. elecoxib. Acetaminophen

12 12 ection D. For each of the following drugs write on the appropriate lines the principal medicinal use and the mechanism of action associated with that use. (10 Points) Medicinal Use: Mechanism: 2. Medicinal Use: Mechanism: 3. 2 Medicinal Use: F 3 3 Mechanism: Medicinal Use: Mechanism: Medicinal Use: Mechanism:

13 13 ection E. For each of the following systematic names, draw the correct chemical structure, including stereochemistry wherever indicated. Partial credit will be given but you will lose points for incorrect chemical symbols, hydrogens missing from heteroatoms, hydrogens missing from carbons labeled, and for having too many bonds to an atom (see below for examples). (20 Points). 1. Benzeneacetic acid, 3-chloro-4-(2,5-dihydro-1-pyrrol-1-yl)-α-methyl- 2. Morphinan-3,6-diol, 17-allyl-7,8-didehydro-4,5-epoxy-, (5α, 6α)-, hydrochloride 3. 2-(Diethylamino)ethyl [1,1 -biphenyl]-2-hydroxy-3-carboxylate hydrochloride 4. 2-Furancarboxamide, -[1-(2-phenylethyl)-4-piperidinyl]--(2-pyrazinyl)-