1 Medicinal Chemistry 410 Exam #3 April 27, 2007 Name: Med. Chem. #

Transcription

1 1 Medicinal hemistry 410 Exam #3 April 27, 2007 ame: Med. hem. # Part. (75 Points) There are 50 multiple choice questions worth 1.5 points each (75 Points). Please use the cantron heet provided. 1. The anticancer drug illustrated below: 2 P is a false feedback inhibitor of De ovo purine biosynthesis. is the metabolically activated form of thioguanine. is selectively incorporated into viral DA The drug illustrated below: 3 3 inhibits the De ovo synthesis of folates in mammalian cells. as its silver salt, is used topically to treat severe burn victims to prevent infection. is a false substrate that mimics p-aminobenzoic acid. a. only b. only c. 1 and only d. and only e.,, and 3. The drug illustrated below: P is primarily used to treat infections associated with DA viruses. requires viral thymidine kinase for activation. is ultimately activated to a mimic of deoxyadenosine triphosphate.

2 4. The drug illustrated below: 2 2 is used to treat amebiasis. 2 s an antifungal agent. 3 nhibits the synthesis of ergosterol The drug illustrated below is: commonly used with cyclophosphoramide to prevent hemorrhagic cystitis. P is administered iv. is used with cisplatin to prevent nephrotoxociity. 6. The drug illustrated below: 3 ( 3 ) The drug illustrated below: is β-lactamase resistant. is orally active. inhibits protein synthesis in bacteria.. is used to inhibit -14 demethylase activity in fungi. blocks estrogen receptors. is an aromatase inhibitor.

3 8. The drug illustrated below: is a mitotic spindle poison. P 2 2 l is a prodrug. 2 2 l is classified as an alkylating agent. 9. The drug illustrated below: inhibits mycolic acids synthesis essential to the cell wall of mycobacteria. irreversibly inhibits thymidylate synthetase. inhibits dihydrofolate reductase in bacteria The drug illustrated below: inhibits 5α-reductase, the enzyme which reduces testosterone to 5α-dihydrotestosterone. has been used to treat prostate cancer. blocks androgenic receptors. 11. The drug illustrated below: l 3 is susceptible to the development of viral resistance. is T cross-resistant with nucleoside reverse transcriptase inhibitors. is a non-competitive inhibitor of reverse transcriptase.

4 2 12. The drug illustrated below: inhibits dihydofolate reductase. inhibits DA synthesis by limiting the Deovo synthesis of thymidine. is leucovorin and is used in rescue therapy. 13. The drug illustrated below: can only be administered by injection is β-lactamase resistant. 3 3 is a cephalosporin. 14. The drug illustrated below: is used to treat tuberculosis. is administered orally. 2 2 e ( 2) 3( 3) 2 binds to DA and produces hydroxy radicals that cause DA strand breaks. 2

5 15. The drug illustrated below: ultimately can get incorporated into viral DA. does cause chain termination of developing viral DA. is effective against RA-containing viruses. 16. The drug illustrated below: 2 is a bifunctional alkylating agent. Pt causes severe nephrotoxiciy, which is its dose-limiting side effect. 2 primarily causes the cross-linking of the two stands of helical DA. 17. The drug illustrated below is: 3 2 is a bacterial protein synthesis inhibitor. is active orally. is β-lactamase resistant. 18. The drug illustrated below: 3 3 is used topically for its antiinflammatory properties. is a glucocorticoid. is used in the treatment of various lymphomas.

6 19. The drug illustrated below: 6 2 require hydrolysis but not metabolic oxidation for its antitumor activity. is a bifunctional alkylating agent. can cause hemorrhagic cystitis as a side effect The drug illustrated below: 3 3 is administered iv only. requires activation by PGRT (salvage pathway). is a prodrug that is converted to 5-U. 21. The drug illustrated below: 2 initially blocks protein synthesis in bacteria. is β-lactamase resistant. targets DA gyrase causing double strand breaks to bacterial DA. 22. The drug illustrated below: requires metabolic activation. ( 3 ) is a monofunctional alkylating agent. is used to treat tuberculosis.

7 7 23. The drug illustrated below: 2 3 has been used to treat hair loss (alopecia) in males. has been used to treat prostate cancer. is an antagonist at 5-α-dihydrotestosterone receptors. 24. The drug illustrated below: 2 2 [ 2 2 ( 3 ) 3 ] 2 is orally active. is a monobactam. is β-lactamase resistant The drug illustrated below is: an inhibitor of mycobacterial arabinosyl transferases. 2 3 used together with other agents in the treatment tuberculosis. used with doxorubicin to prevent cardiotoxicity The drug illustrated below is: a potent mineralocorticoid. can be administered orally does have some glucocorticoid activity.

8 27. The drug illustrated below: acts by targeting topoisomerase. is known to exhibit cardiac toxicity. extravasation of this agent is associated with severe necrosis at the site of infusion. 28. The drug illustrated below: 2 inhibits viral DA polymerase. is a 2 deoxyguanosine mimic. is initially phosphorylated by viral thymidine kinase. 29. The drug illustrated below: is a non-nucleosides reverse transcriptase inhibitor.. does have antiangiogenic properties. inhibits multiple receptor tyrosine kinases. 30. The drug illustrated below: inhibits 14α-demethylase in the biosynthesis of ergosterol. is primarily, if not exclusively, used topically. inhibits squalene expoxidase.

9 31. or the drug illustrated below: 2 cross-allergenicity could occur in individuals allergic to sulfonamide antibiotics. it is used only in combination with ritonavir to achieve sufficient plasma concentrations. is a V protease inhibitor. 32. The drug illustrated below is: 3 a highly effective Gram (-) antibiotic. orally active. 2 a β-lactamase inhibitor The drug illustrated below: is administered orally. inhibits ribonucleotide diphosphate reductase. 2 is used a sensitizing agent in radiotherapy. 34. etuximab, Erbitux. is a monoclonal antibody that binds to the receptor for epithelial growth factor. is an anti-angiogenic agent. is a monoclonal antibody that binds to vascular endothelial growth factor

10 34. The drug illustrated below: Ac 6 acts as a mitotic spindle poison by inhibiting the disassembly of microtubules. if formulated with cremophor EL, can be administered orally. acts as a mitotic spindle poison by destabilizing microtubules and promoting their dissolution. 36. The drug illustrated below: 3 2 can be used as progesterone agonist. can be administered orally. is used as an abortifacient with a PGE 2 prostaglandin. 37. The drug illustrated below is: is incorporated into viral DA. is a pro-drug. is a thymidine mimic. ( 3 ) 2

11 38. The drug illustrated below: 3 11 (3) is not cross allergenic with penicillin antibiotics. forms a ketal intermediate at low p that is associated with stomach cramping. is acid labile and tablets need to be enteric coated. 39. hronic is uncontrolled growth of B- or T-lymphocytes. Myelogenic Leukemia (ML) can often be treated effectively with the tyrosine kinase inhibitor matinib mesylate (Gleevec is the uncontrolled growth of granulocytes. 40. The drug illustrated below: 3 3 is used to prevent hair loss. is a metabolite of estrogen.. is the most potent androgenic metabolite of testosterone 41. The drug illustrated below is: used to prevent hemorrhagic cystitis associated with the administration of cyclophosphoramide or ifosphamide. 2 2 a activated by alkaline phosphatase. used to prevent renal toxicity associated with the administration of cisplatin.

12 42. The drug illustrated below: has an anabolic:androgenic ratio of 3:1. is an orally active synthetic estrogen. is an aromatase inhibitor. 43. The drug illustrated below: s a glucocorticoid. s used as an inhalant in the treatment of asthma. s used as an abortifacient. 44. The drug illustrated below: Trastuzumab, erceptin is a monoclonal antibody for the treatment of erpes viral infection. is used in the treatment of non-odgkin s lymphoma that possess the membrane bound phosphoprotein, D-20. is a monoclonal antibody used to treat metastatic breast cancers that overexpress human epidermal growth factor BG instillation refers to the administration of bleomycin together with cyclophosphoramide and gemcitibine into the urinary bladder. is used for the treatment of superficial bladder tumors. refers to the administration of an inactivated form of the bacterium Mycobacterium tuberculosis into the urinary bladder.

13 46. The drug illustrated below is: 13 3 inhibits squalene epoxidase in the synthesis of ergosterol. is not used orally, but is effective topically for Tinea infections. inhibits 14α-demethylase in the biosynthesis of ergosterol. 47. The drug illustrated below is: primarily used to treat tuberculosis. selectively binds to ergosterol. primarily used as an antifungal agent. 48. The drug illustrated below: 3 ( 3 ) 2 2 targets topoisomerase converting this enzyme into a cellular poison. can discolor and retard growth of developing teeth in children. can be administered orally.

14 49. The drug illustrated below: is used in combination with nucleoside reverse transcriptase inhibitors that mimic thymidine or 2 -deoxycytosine. must be converted to a 5 -triphosphate to be active. is metabolically converted to a mimic of 2 -deoxyadenosine. 50. The drug illustrated below: 3 inhibits DA polymerase, while increasing RA polymerase. stabilizes the cleaved complex formed between a topoisomerase enzyme and DA. can be administered orally. 3 3 Part 2 Generic ames (9 Points). Provide the Generic ames for the ompounds listed on the following page. n the space provided under the structure of each the compounds illustrated, write the correct APTALZED letter corresponding to the choice of answers given on the bottom of the page. The letter Z may be used as an answer as seldom or as often as needed.

15 l P() 2 6' P ( 2 2 l) 2 3 A. yclophosphamide J. Progesterone. Mitoxanthrone B. Doxorubicin K. Estrone T. Betamethasone. hloramphenicol L. Amoxicillin U. Ribavirin D. idofovir M. Aldosterone V. ytarabine E. amciclovir. inasteride W. Pyrimethamine. Tobramycin. Ertapenem X. Piperacillin G. ephalexin P. Voriconazole Y. lavulanic Acid. Moxifloxacin Q. Terbinafine Z. one of These. ulfamethoxazole R. Ritonavir l a

16 Part 3 omenclature 16 Points. When using the basic templates provided insert all unsaturation as required and specify the orientation of all functionality or hydrogen atoms by using BLD lines/wedges or AED lines/wedges. Example 16 3 R 3 T β-ydroxy-1α-methyl-17-propyl-5-α-androstan-3-one [known as Rosterolone] 2. 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-(3-chlorophenyl)-6-(2-hydroxyethyl)- 4-methyl-7-oxo-, 4-[4α,5β,6β]-

17 17 3. Pregn-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-16-methyl-, (6α,11β,16α) Quinolinecarboxylic acid, 5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)- 6,8-difluoro-1,4-dihydro-4-oxo-, cis-(parfloxacin, Zagam ) Exam Total: Part 1. Multiple hoice Part 2. Generic ames Part 3 omenclature 75 Points 9 Points 16 Points Total