Medicinal Chemistry 410 Exam #1 February 20, 2009 Name: Med. Chem. #

Transcription

1 Medicinal Chemistry 410 Exam #1 February 20, 2009 ame: Med. Chem. # 1 Part. (75 Points) There are 50 multiple choice questions worth 1.5 points each (75 Points). Please use the cantron heet provided. f you feel there is no correct answers, leave the cantron blank for that particular question and write E on your exam for that question. 3 C 2 6' 2 2 C 1. The drug illustrated below: F C 3 C 2 causes double-strand DA strand breaks in bacteria. should not be taken with antacids. is active orally. 2. The drug illustrated below has which of the following properties: C 3 C C 3 C C 3 3 a a β-lactamse resistance. orally efficacious. cross allergenicity is common in patents sensitive to pencillins. 3. The drug illustrated below: 2 C is very effective against anerobic bacteria. is resistant to β-lactamase. is a nephrotoxic and ototoxic.

2 2 4. The drug illustrated below: 2 3 C C 3 C C 2 C 2 is orally active. is β-lactamase resistant. inhibits bacterial cell wall synthesis by inhibiting penicillin binding protein ( a transpeptidase). 5. The drug illustrated below: C 3 is contraindicated for individuals allergic to sulfonamide antibiotics inhibits the De ovo synthesis of dihydrofolate in bacteria. is used to treat bacterial urinary tract infections (UT s). a. only b. only c. 1 and only d. and only e.,, and 6. The drug illustrated below: P 2 C C 2 C 3 C C 3 C 3 C C 3 2 is associated with chain termination in the synthesis of viral DA. is converted to a mimic of 2 -deoxyadenosine triphosphate. is ineffective in viruses with a deficiency in viral thymidine kinase. 7. The drug illustrated below: F F C 3. can be used iv for systemic fungal infection. F inhibits squalene epoxidase. inhibits dihydrofloate reducase. 2

3 8. The drug illustrated below: 3 is used to inhibit the spread of V infection. is T effective orally. is a neuraminidase inhibitor. 9. The drug illustrated below: 2 C 2 2 C 3 inhibits dihydrofolate reductase in bacteria. is synergistic when used with sulfonamide anibiotics. blocks protein synthesis by binding to ribosomal RA. 3 C C The drug illustrated below: is resistant to β-lactamase. 2 C C 3 is an inhibitor of transpeptidase. is effective orally. C 3 C 11. The drug illustrated below: C 3 is used to treat erpes implex infection. is dependent upon viral thymidine kinase for activation. when used properly, can prevent V transmission to the newborn.

4 12. The drug illustrated below: 3 C C 3 C C 3 C 3 inhibits bacterial cell wall synthesis. is bactericidal. is resistant to β-lactamase The drug illustrated below: is a prodrug. C 3 C 2 C 2 C C 3 C 3 is β-lactamase resistant. is T effective orally. 14. The drug illustrated below: is effective orally. is a monobactam antibiotic. is a potent antibiotic toward gram (-) bacteria 15. The drug illustrated below: 2 2 C is used in combination with the thymidine mimic, Zidovudine (AZT). does cause chain termination of developing viral DA. is effective against RA-containing viruses.

5 2 16. The drug illustrated below: 3 C C 3 has a long duration of action. is effective as an antimalarial agent (with pyrimethamine). will not be cross-sensitive in individuals allergic to sulfa drugs The drug illustrated below is: C 3 (C 3 ) 2 is a bacterial protein synthesis inhibitor. rarely is associated with allergies. 2 inhibits β-lactamase. 18. The drug illustrated below: is effective orally. is β-lactamase sensitive. is a third generation cephalosporin. 19. The drug illustrated below: C 3 3 C 3 C 3 C 3 C 2 C C 3 3 C C 3 C 3 3 C C 3 C 3 C 3 C 3 is a protein synthesis inhibitor. undergoes internal ketalization that is associated with G upset. must be enteric coated for oral administration.

6 20. The drug illustrated below: is resistant to β-lactamase C C C 3 is orally active. is more active than ampicillin to gram (-) bacteria C 3 such as Pseudomonas aerogenosa. C 21. The drug illustrated below: F C 3 C 2 targets the enzyme DA gyrase and converts it into a cellular poison. is associated with increased risk of tendinitis and tedon rupture. initially blocks protein synthesis in bacteria The drug illustrated below: C 3 C 2 C is a potent broad spectrum antibiotic that can kill gram (-) bacteria. is orally active. is a β-lactamase inhibitor. 23. The drug illustrated below pre-birth and after-birth exposure: C 3 (C 3 ) 2 can cause permanent discoloration of developing teeth in children. 2 can cause discoloration of developing bone in children. can cause distorted structural development of teeth in children.

7 24. The drug illustrated below: 7 is an antibacterial agent that blocks protein synthesis by bind to the 30 portion of ribosomal RA. is effective orally. is used as a prophylactic to prevent malarial infection. 25. The drug illustrated below is: is activated to an inhibitor of dihydrofolate reductase. is used in combination therapy to prevent the parasitic disease, malaria is seldom used because of toxic side effects. 3 C 26. The drug illustrated below is: used as monotherapy for the treatment of V infection. is used to prevent influenza type A and type B. is an integrase inhibitor. 27. The drug illustrated below: 3 C C C 3 lacks the cross resistance observed among several nucleoside reverse transcriptase inhibitors (RTs). is a competitive inhibitor of viral reverse transcriptase. is used as monotherapy for early-stage V infection.

8 28. The drug illustrated below: 2 C C 2 2 C(C 3 ) 2 is a 2 deoxyguanosine mimic. is a prodrug. requires phosphorylation by viral thymidine kinase for activity. 29. The drug illustrated below: a inhibits viral DA polymerase. P C is orally active. a is dependent upon viral thymidine kinase for activation. a 30. The drug illustrated below: F F binds to ergosterol and disrupts the cell membrane of fungi is used systemically. inhibits 14α-demethylase in the biosynthesis of ergosterol. 31. The drug illustrated below: 8 cannot be administered orally.. is a V protease inhibitor. acts as a transition state enzyme inhibitor.

9 3C 3C 32. The drug illustrated below is: Bacitracin is effective against gram (+) bacteria. has a core structure that consists of cyclic peptide. can not be administered iv because of nephrotoxicity. 33. The drug illustrated below is: C3 3C The drug illustrated below: binds to bacterial DA dependent RA polymerase. binds to the D-ala-D-ala terminus of peptidoglycans in bacteria, blocking access by transferases. binds to ergosterol. 9 is a prodrug is used to treat hepatitis B requires viral thymidine kinase for activation. 35. The drug illustrated below: is a non-nucleoside reverse transcriptase inhibitor. is a non-peptide based V protease inhibitor. is used for V infections that have become resistant to other protease inhibitors.

10 36. The drug illustrated below: 10 2 C C 3 C 3 C 3 C is orally active. is not resistant to β-lactamase. is used primarily to treat gram (-) bacteria. 37. The drug illustrated below ultimately acts as a guanosine mimic. can be synergistic with AZT (a thymidine mimic). is ultimately incorporated into viral DA. 38. The drug illustrated below: 3 C 3 C 3 C C 3 C 2 C 3 C 3 3 C C 3 C 3 3 C C 3 C 3 C 3 C 3 is resistant to β-lactamase. cannot form the ketal intermediate at low p that is associated with the stomach cramping of other macrolide antibiotics. is not cross allergenic with penicillin antibiotics. C 39. The drug illustrated below: is used topically to treat severe burns. is a prodrug. is activated by bacterial azo-reductase (or nitroreductase).

11 3 C 40. The drug illustrated below: C 2 F 11 is a protein synthesis inhibitor. binds to the 23 ribosomal subunit of ribosomal RA. is used to treat vancomycin-resistant MRA infections. 41. The drug illustrated below is: 2 C 2 F is a deoxycytosine mimic. is primarily used to treat infections from DA-containing viruses. is a mimic of thymidine. 42. The drug illustrated below: 3 C 3 C 3 C C 3 C 3 can be used together with other V protease inhibitors. is known to inhibit several CYP450 enzymes. is used to treat severe fungal infections. 43. The drug illustrated below is: 2 is a mimic of deoxyadenosine. is indicated for the treatment of epatitis C viral infection. is a mimic of deoxyguanosine.

12 44. The drug illustrated below: 12 is orally efficacious for treating Clostridium difficle infection in the G tract, but not orally efficacious for systemic infections.. inhibits bacterial cell wall synthesis in bacteria. Cannot be administered iv because of its nephrotoxicity 3 CC 3 C 45. The drug illustrated below: C C 3 3 CCCC 3 inhibits squalene epoxidase in the synthesis of ergosterol. C 3 cannot be not used orally, but is effective topically for Tinea infections. inhibits 14α-demethylase in the biosynthesis of ergosterol. 46. The drug illustrated below is: C 3 C 3 C 3 3 C C 3 C 3 binds to ergosterol producing an antifungal effect. known to induce cytochrome P450 enzymes, such as CYP450 3A4. Binds to mycobacterial DA dependent RA polymerase. C 3 C 3

13 47. The drug illustrated below: 13 has side effects that are severe and often fatal. is used as a preventive agent for malarial infection. can be administered orally. 48. The drug illustrated below: 2 2 C is used in combination with nucleoside reverse transcriptase inhibitors that mimic thymidine or 2 -deoxycytosine. must be converted to a triphosphate for it be ultimately active. is metabolically converted to a mimic of 2 -deoxyguanosine. 49. The drug illustrated below: 2 is an orally active. is used to treat hepatitis C is only administered parenterally. 50. The drug illustrated below: is a prophylactic agent used to prevent the uncoating of influenza A. is orally active. binds to the receptor that V uses to bind and gain entry (CCR5) to human T cells.

14 Part 2 Generic ames (9 Points). Provide the Generic ames for the Compounds listed on the following page. n the space provided under the structure of each the compounds illustrated, write the correct CAPTALZED letter corresponding to the choice of answers given on the following page. The letter Z may be used as an answer as seldom or as often as needed. 14 Cl C C CF 3 3 C 2 C 3 Cl 2 C C 2 2 (C 3 ) 2 C Cl C 2 C C 2 Cl C 2 C Cl C Cl C 2 C 3 C 3 C C3 C 3 C 3 C C 3 C 3 C 3 Cl C C CF 3 2 C 3 C 2 C C 2 C 3 C 2

15 15 A. Cefixime, J. Minocycline. Griseofulvin B. Kanamycin K. Acyclovir T. Rifabutin C. Chloroquine L. Amoxicillin U. soniazid D. Relenza M. Zidovudine V. Ciprofloxacin E. ulfadiazine. Miconazole W. Ethambutol F. Efavirenz. aquinavir X. Aztreonam G. Erythromycin P. Entecavir Y. ulbactam. Chloramphenicol Q. Ribavirin Z. one of These. ulfadoxine R. xacillin Part 3 omenclature 16 Points Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(carboxy-3- thienylacetyl)amino]-3-methoxy-8-oxo-, 6R-[6α,7β(R*)] 2. 3-Quinolinecarboxylic acid, 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-8- methoxy-1,4-dihydro-4-oxo Purine-6-one, 2-amino-1,9-dihydro-1-methyl-9-[(2-hydroxyethoxy)methyl]-

16 16 4. Benzenesulfonamide, 4-amino- 1 -(4-methyl-5-isoxazolyl)- Exam Total: Part 1. Multiple Choice Part 2. Generic ames Part 3 omenclature 75 Points 9 Points 16 Points Total