Med Chem1 06001

Med Chem1 06001 - Medicinal Chemistry 311 Mt October 3 2006 ‘x Examination#1 B Per50 “n u ii N Use a No 2 pencil “x Write your name on the

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Unformatted text preview: Medicinal Chemistry 311 Mt October 3, 2006 ‘x Examination #1 B Per50\ “n u ii- , N Use a No. 2 pencil. “x Write your name on the top of this exam and on the front and back of the bubble the back of the bubble sheet. DO NOT USE YOUR SOC. SEC. NUMBER! Fill in bubble sense where applicable. DO NOT erase marking in "TEST FORM" column! For the multiple choice questions, select the one best answer. For each question, the correct answer is worth 2 points. Read each question carefully. Double check all your answers! If you change an answer, be certain to erase the original answer completely! 1. Which of the following drugs cannot be produced by fish or farm animals? la? curare b vitamin D / c) estrone / d) hydrocortisone / e) insulin / 2. Which of the following drugs is not made by plants? quinine ‘ meperidine c) atropine cl) digitalis e) colchicine 3. Which of the following may be useful for the extraction of ephedrine from the ephedra plant? a) distilled H20 b) aqueous KOH © aqueous HCl d) vegetable oil e) concentrated H2804 4. Which of the following drugs contains a 3-membered ring in its structure? a) sulfanilamide b) penicillin G) phenobarbital d) morphine @ ciprofloxacin 5. Which of the following drugs contains a cyclopropyl ring in its structure? a AZT ciprofloxacin c penicillin d) methotrexate e) phenobarbita 6. Which of the following approximates best the percentage of drugs obtained by chemical synthesis in the USA? a)6% b)7% c) 12% d) 25% @50% 7. Which of the following drugs is not produced by microorganisms? I @ reserpine b) tetracycline c) human recombinant growth hormone d) penicillin e) streptomycin 8. Which of the following drugs is made by organic chemical synthesis? a) digitalis b) morphine c) reserpine ® phenobarbital e) vancomycin 9. Metabolism of cocaine by CYP450 and esterases may produce all but one of the followmg: / O OCH3 » a) benzoic acid\€Q ' r ’1’"- ' b) acetaldehyde CH‘XN c) methanol— 3 l t d) secondary amine cocaine (no @ secondary alcohol 10. Which of the following cannot be produced in bacteria using recombinant DNA technology? a) alpha-interferon b) glycoprotein hormones c) tissue plasminogen activator E) erythropoietin e) human insulin 11. The pKa of acetic acid changes, if it is substituted by X to give XCHchOH. Which of the following will change the pKa most? ‘ a) X = N02 b) X = methyl c) X = ethyl d) X = l @X=F 12. Which of the following drugs was developed by rational design? a) prontosil b) penicillin © captopril d) tetracycline e) streptomycin 13. The absolute configuration of a drug may affect all but one of the following: a) the magnitude of pharmacological effect b) the type of pharmacological effect c) liver metabolism (a passive diffusion across membranes ‘ intestinal absorption 14. Drugs A & B injected iv, bind to the same site on serum albumin in the blood. For drug A, the dissociation constant KD = OQQirLM ; for drug B, Kn = 9,.1J11M. Considering protein binding only, which of the following statements is false? a) the concentration of free drug A in the blood in the absence of drug B is less than the dose administered \/ r b) bound to serum albumin, drug A cannot be metabolized / 0 drug B has a lower affinity to serum albumin than drug A ‘/ when A & B are present, co—administration of B may require increasing the / dose of A e) drug A binds more strongly to serum albumin than does drug B \/ 15. The solubility of drug A in n-octanol is 15 mglmL and in water it is 3 mglmL. The value of P for drug A is which of the following: (6’ .a) 0.05 I”) b) 0.2 4 c) 0.5 J d) 2.0 @ 5.0 16. Nicotine is more readily absorbed by the kidneys from alkaline urine than acidic urine. Is this statement true or false? H6) (a? TRUE \ N\ b) FALSE l N/ CH3 nicotine 17. Which of the following statements about benzo(a)pyrene, a component of cigarette smoke, is false? a) its toxic metabolites may be conjugated with glutathione b) its toxic metabolites can alkylate DNA Q3) its Ames test gives negative results d) it is oxidized to epoxides by CYP450 e) it is a procarcinogen benzolalpyrene 18. Which of the following statements about drug metabolism is false? a) it is carried out mainly in the liver b) it is localized in the microsomal subcellular fraction c) it makes drugs more polar d it makes drugs less lipid soluble 6 it makes drugs more easily reabsorbed by the kidneys 19. All but one of the following will be produced during activation of the prodrug bacampicillin: \/ 4 O n . Li a) ampucullin W a“ L 0M, b) ethanol?‘ NH N . 2 1 c) methanol 0 a . C” CO” bacam ici lin e) acetaldehyde p I O 20. Which one of the following drugs requires reductive metabolism for activity? a) PGFZOL b) imipramine © sulindac d) tolbutamide e) cyclophosphamid 21. Which of the following reactions yields salicylic acid from aspirin? a) acetylation OCOCH3 OH b) reduction ©: ©: c) hydroxylation COOH COOH © hydmes's aspirin salicylic acid e) oxidation 22. Most efficient distribution of a drug in the body requires an optimum range of logP values - neither too high, nor too low. Is this statement true or false? cD'TRUE b)FALSE 23. Polar drugs acting on the central nervous system (CNS) cannot have access to the brain by passive diffusion. Is this statement true or false? épTRUE b)FALSE 24. Which‘ of the following amino acids is part of the structure of methotrexate? a) methionine NH2 ~ b) glutamine / N COOH c) IYSine N i CONH‘Egfi d) asparagine \N / CH3 . . N @ QIUtam'C ac'd methotrexate 25. Prodrugs may be designed to achieve all but one of the following goals: COOH a) to increase duration of action (5) to decrease duration of action c) to increase lipid solubility d) to decrease water solubility e) to block conversion to parent drug 26. Characteristic metal-ligand bonds in chelates are called: a) H—bonds b) hydrophobic bonds ionic bonds coordination bonds e) covalent bonds (E7. The Ames' test shows that a candidate drug may be all but one of the following: a) genotoxic / b) toxic to Salmonella 0) potential carcinoge _ d) potential procarcinogen/ @l potential Mogen 28. is the following statement true or false? OH-groups formed in phase l metabolism may become conjugated in phase II metabolism. TRUE m FALSE 29. Which one of the following groups may form conjugates with glutathione: a) hydroxy ® epoxy c) carboxy d) amino e) phenyi 30. What is the percentage of the ionized form of phenobarbital in urine at pH of if phenobarbital's pKa = 7.2? a 0.990% O G) O c) 2610/? hi i NH d) 90.9% 0/ N 0 90 \N 0 e) 99% phenolblarbital 31. Administration of an inducer of drug metabolism, like the barbiturates, may require a decrease in the dose of another drug present to achieve the same therapeutic effect as without the inducer. True or false? a) TRUE ® FALSE 32. Maximum oral bioavailability requires all but one of the following conditions: a) efficient absorption from the GIT tract / ‘ b) adequate water solubility v/ c maximum lipid solubility v’ minimum first pass effect e) complete swallowing of the dose 33. After the administration of NaH003 to a patient overdosed on phenobarbital, all but one of the following contribute to the patient's recovery: a) ionization of the drug in the urine b increased water solubility of the drug in the urine increased reabsorption of the drug by the kidneys ) elevation of the urinary pH e) increased elimination of the drug 34. Binding of drugs to receptors is stereoselective. True or false? Q TRUE b) FALSE 35. The vasoconstrictor octapeptide angiotensin ll is a product of the cleavage of angiotensin I by angiotensin converting enzyme (ACE), a dipeptidyl carboxypeptidase. How many amino acids make up angiotensin I? a)4 b)6 c) 7 d)8 "@510 36. The morphine molecule can potentially undergo metabolism at multiple sites. Which one of the following reactions cannot be responsible for formation of morphine metabolites in the body? HO a) sulfate conjugation b ~N-dealkylation O oxidatiorggcfketone d) oxidation to an aldehyde Ho / INCH3 e) glucuronide conjugation _ morphine 37. The biproduct of the oxidative dealkylation of the antidepressant imipramine to form desimipramine can be further metabolized to which of the following? a) acetaldehyde b) acetate c) ethanol Kk ”—’ i Mp d) methanol rm“ @ formate _ _ _ I _ “HTCH3 Imlpramme CH3 deSImIpramIne 38. The biological activity of N-mustards, such as anilino mustards and cyclophosphamide, involves all but one of the following: a) chemical reactivity b) aziridium ion formation c) covalent bond formation ‘8) reaction with electrophiles e) crosslinking of double stranded DNA 39. Replacement of the methyl group on the aromatic ring of tolbutamide with chlorine may results in all but one of the following: 0 ll . . . CH3 S—NH—CO—NH/\/\ a) increased duration of action 3 r b) Increased half llfe tolbutamide c) increased resistance to CYP450 oxidation enhanced elimination by the kidneys e prevention of the formation of a benzoic acid derivative 40. Individual variations in drug metabolizing enzymes may not be due to: a) genetic polymorphism (9) serum protein binding / 0) disease state d) mutations in one allele coding for the enzyme e) mutations in both alleles coding for the enzyme 41. Which of the following is not correct regarding the active transport of polar drugs? a) energy requiring b) carrier mediated (5) cannot discriminate between enantiomers d) can transport drugs against their concentration gradient e) accompanied by ATP hydrolysis 42. Which of the following statements about the red dye prontosil is false? H N a) it can cure bacterial infections 2 «lg it is a prodrug of sulfanilamide H2N N=N-©-302NH2 it requires metabolic oxidation for activity . prontosrl d) it is not active in vitro a) it has an azo-linkage between 2 aromatic rings 43. Which of the following is not required for CYP450-catalyzed reactions? a) 02 @ H20 c) NADPH d) heme a) Fe2+ 44. Enantiomers of drugs differ from each other in all but one of the following: a) smell b) taste c) protein binding d) optical rotation water solubility 45. Which one of the C-atoms (9) below is not susceptible to metabolic hydroxylation? 3) 'QHa b) -NH_QH3 0) -§H(CH3)2 d) 'Q(CH3)3 e) aromatic ring -§H (para—position) 46. All but one of the following may play a role in the lethal toxicity of 6- mercaptopurine (6-MP) to a small population of cancer patients: enzyme deficiency c genetic polymorphism / d) excess thiopurine levels in the bone marrow >/ e) reduced metabolism of the drug / a reactivity of the mercapto-group of 6-MP / 47. Racemic drugs are equal mixtures of 2 enantiomers. is this statement true or false? a TRUE FALSE - _ 48. Which one of the following statements about sulfasalazine is false? a) it has anti-inflammatory activity 0 b) it is metabolized by bacterial azoreductaseHO 0 @ it is used to treat ulcerative colitis H N=N—©—§—NH—(/:\> it is readily reabsorbed by the kidneys o N" e) it is a proprug targeted to the large intestine sulfasalazine 49. if warfarin binds to serum albumin 99%, and administration of another drug displaces 5% of the bound form of warfarin, how many fold should the dose of warfarin be decreased to produce the same therapeutic effect as in the absence of the other drug? I 7 _ r I v, r a) 2x W» b) 3x c) 4X d) 5X @6X 50. Mammalian cell membranes contain all but one of the following components: a) phospholipids b) cholesterol (7:) hemoglobin d) glycoproteins e) lipoproteins ...
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This note was uploaded on 12/16/2009 for the course MCH 311 taught by Professor Kalman during the Spring '08 term at SUNY Buffalo.

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Med Chem1 06001 - Medicinal Chemistry 311 Mt October 3 2006 ‘x Examination#1 B Per50 “n u ii N Use a No 2 pencil “x Write your name on the

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