mcI04e3 - Medicinal Chemistry I Examination Name _December...

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Unformatted text preview: Medicinal Chemistry I Examination Name _December 3 . 2004 Med. Chem. # Part I (9) points) 1. Indicate BRIEFLY and SPECIFICALLY the difference. ifany. in the MECHANISM OF ACTION between the following two drugs. When requested. provide the generic name of the drug. Q [CH3 ooH3 H C—N CH NHCH C O 21 t I 2 2 H2 OCH3 CH2 CH20H2 OCH3 CHOH . I 9H2 “2&0 (H3C)2HC‘C-CN NP 0 H OCH3 Generic Name: 2. Indicate BRIEFLY and SPECIFICALLY the difference. if any. in the MECHANISM OF ACTION between the following two drugs. When requested. provide the generic name ofthe drug. 0 H C O 3 \ [\G 0 H20 l) N O N” ‘ N Hac OFT? H—N / ® HC ‘L/ N O f2 Cl 3 Nt O <:><O:]/\N NHZ CH3 0 H Generic Name: 3. Indicate BRIEFLY and SPECIFICALLY the difference. if any. in the MECHANISM OF ACTION between the following two drugs. When requested. provide the generic name ofthe drug. CIEHZNHCH(CH3)2 oHOH Generic Name: Ix) Part II: (9 Points) 1. Indicate BRIEFLY and SPECIFICALLY the difference. if any. in the principal MEDICINAL USE between the following two drugs. When requested. provide the generic name of the drug. o H W043 "OH H H OH Generic Name: 7. Indicate BRIEFLY and SPECIFICALLY the difference, if any, in the principal MEDICINAL USE between the following two drugs. When requested. provide the generic name of the drug. 0 CH2C0C2H5 Hnm." H30 ,C t H CHZCHZ :\ ,,o \NHCIC H N H Cl O\\S//O "/ \ \NH (Q0004 I / / H N CH3 3. Indicate BRIEFLY and SPECIFICALLY the difference. if any, in the principal MEDICINAL USE between the following two dnlgs. When requested. provide the generic name of the drug. 0 Wflmzlacw Generic Name: C:o IQ 9 09 H H3C-§\N Ca 0\ I /CHZCH3 0 éHa CH2CH2-N\ 2 CHZCH3 Generic Name: Part III: (l2 Points) Case 1. (4 Points) “Dr. Death" is back in town making as many mistakes as he did bclore his summer vacation. He has prescribed the following medications to an individual diagnosed with hypertension: OH CH2- (l3— CHZN H- CH(CH3 )2 0’ l O O H \\ HzN’n ./ S\N@ G) O \ I A Na Cl N Drug A Drug B After being on these mediations for 6 weeks. Dr. Death takes a blood sample and finds that this patient has hyperuricemia, elevated triglycerides. and low HDL levels. He prescribes the following lipid lowering agents (Drug C and Drug D) with the recommendation that all four mediations be taken together in the morning. The patient‘s pharmacist speaks to the patient and hears about the Dr. Death‘s concern about the elevated uric acid and serum triglyceride levels. as well as the low HDL levels. He then looks at the patient’s prescription history and shakes his head. hIi—CHZCHZ ir— ‘in 9 HCIJ-OH \ c.OH 9‘2 [T N-CHz-CHZ N— / I I? N Drug C Drug D The pharmacist has a specific concern regarding the administration of the following pharmaceuticals based on this patients drug regimen and latest blood analysis. Briefly explain what you think are his concerns. 1. With Drug A alone: 2. With Drug B alone: 3. With Drug C alone: 4 With Drug D administered together with possibly Drugs A, B, or C. (List all relevant) Case 2 14 Pointsl A young women is being treated [or hypertension using Drugs E. F. and a low dose of G. She is also given Drug H because of elevated LDI. levels. Alter being on these medications for six months her blood pressure has been cl‘l‘ectively controlled. but she has developed an arrhythmia. The pharmacist in reviewing her mediations realizes that the physician may have made a mistake. o 0 ll“ \\ otc ocszHQc” H Cl ), CNHCNHz \I H o HzN 1N NH. Drug E i‘ Cl NYCH3 0\ I I is. N HZN O 0 H30 Drug G Drug H 1. Based upon the medications that she is taking. what two drugs might be responsible for the apparent drug-induced cardiac arrhythmia? What ONE addition or deletion would you suggest regarding this patient drug regimen. Add or Delete: 2. This patient is experiencing a dry unproductive cough. what related class of drugs could be used as an alternative that would provide a similar benefit regarding lowering her blood pressure. but without causing this cough. Name the Class of Drug: In view of this patient‘s age. suggest two other modifications to the drug regimen that you would con51der recommending to the physician. 5 3. Recommendation #1 4. Recommendation #2 _ Case 3 (4 Points) An individual is rushed into the emergency room. He is a type 2 diabetic. It appears that he is hypoglycemic. He had been taking Drug I (which caused insulin—release and lowers blood glucose levels) to control his blood glucose levels. His wife said that there was no way that he could have taken an overdose as he uses a daily pill monitor. She has not seen this ever happen to him since the one time he took several aspirins (acetylsalicylic acid) several years ago for a sprained ankle. At that time he also he became severely hypoglycemic. The only new medication that he was just starting to take was Compound J (400 mg/day) to improve his blood lipid profile and to reduce his potential for arteriosclerosis. Compound J has not shown any adverse effects in normal individuals or in individuals with type 1 diabetics. The physician assumes you know the chemical nature ot‘ these agents better then he does and asks if you could provide some explanation as to what is at the root of this problem. ('3' O c\ C :1 OH O O H II 0\ c1 fi—NH—C—NH—CHZCHZCH3 (3:0 (31—130 / 3C Cl CH O / 3 0 N\C’/ / I NH2 0 H J Drug l Aspirin Drug \\ /OCH3CH3 PLASMA PROTEIN fifififi ILLUSTRATE (nonessential features of the Drug Molecules can be abbreviated) how specific sites on plasma protein are likely involved (2 Points). Then provide a BRIEF EXPLANATION for basis for the patient's condition (2 Points). 6 Part IV. (54 Points 27 Questions 2 Points Each): . Select the best answer for each of the following. If no suitable answer is provided write “NONE” in the Space provide. 1. The drug illustrated below: I Is principally used to treat hypertension. [I Is an angiotensin II antagonist. [ll ls a phosphodiesterase inhibitor-type 5. a I only b [11 only c I and 11 only (1 ll and III only 6 I. II. and III Answer 2 I Is a prodrug. 11 Can produce a non-productive cough. Is an angiotensin-converting enzyme inhibitor. a I only b 111 only c I and 11 only d II and Ill only e I. II, and 111 Answer 3. Inhibits cholesterol absorption. Is a vasodilator. Used to reduce pulmonary hypertension. a I only b III only c l and Il only d II and Ill only 6: I. II, and 111 Answer 4. The drug illustrated below: I Is used to treat angina. [I Can be administered sublingual. III [S available as a transdermal patch. a I only b 111 only c I and II only d II and III only e I, II. and III Answer 5. The drug illustrated below: I Physically displaces norepinephrine from storage granules. 11 Is an dz—agonist (central). [[1 Blocks the refilling of norepinephrine in storage granules. I only 111 only I and 11 only 11 and 111 only I, II. and III Answer (DO-00‘s): 6. The drug illustrated below: Is a thiazide diuretic. Can cause edema as a side effect. Is a peripheral vasodilator. a I only b Ill only c I and I] only d 11 and III only e I. II, and III Answer 7. The drug illustrated below is: —CH-CH2-CH—CH2—-- [ Is an enzyme inhibitor. II Can be administered iv. (9 III Binds bile acids and prevents their reabsorption. —CH2-CH2 CH2N(C H3)3 a I only b 111 only c l and II only cl II and Ill only e I, II. and III Answer 8. The drug illustrated below is: Is used as an antihypertensive agent. Is used for symptomatic relief in individuals with benign prostatic hyperplasia. ls associated with orthostatic hypotension as a side effect. a I only b Ill only C l and Il only d 11 and 111 only e I, II, and 111 Answer illustrated below is: \C E! 3 .9. Is used to treat glaucoma Is used to treat hypertension. Is an (12 agonist (central). a I only b 111 only c I and 11 only d II and 111 only e I, II. and III Answer 10. The drug illustrated below is: A prodrug. Increases Lipoprotein Lipase activity. A Class 18 antiarrhythrnic agent. a. I only b. III only c. l and 11 only (I. II and III only e. I, II, and 111 Answer 1 l. The drug illustrated below: Is a Loop diuretic. Is a Pregnancy Category C drug. Can cause hyperkalemia. I only III only I and II only II and III only I, II. and III Answer (DO-.0693 12. The dru illustrated below: Is extensively eliminated unchanged in the urine. ls administered orally. Is a Class lB antiarrhythmic agent a I only b III only c l and I] only d II and Ill only e 1. [Land III Answer I3. The dru illustrated below: 0 o H CH2(CH2)2CH2‘T_CH2‘C:JN§ I Is an antagonist at angiotensm 11 receptors. [1 Is a prodrug. III Is 50% eliminated in the bile. (CHalch'CH ; b H o CHZCHg I only 111 only 1 and II only II and [[1 only I, II, and III Answer (DD-00"” 14. Geo I s a potent vasodilator. CH3 ls available in an iv formulation. oCHchzN: _ CH2 Is used to treat hypertensmn. a I only b 111 only C I and II only d II and III only I, II. and III Answer lb. The drug illustrated below is: (D l Displaces norepinephrine from storage granules. 11 Can cause hypertension if initial dosing is not gradual. [11 Will cause rebound hypertension upon sudden withdrawal. a I only b III only c I and II only d II and 111 only e I. II. and III Answer 10 16. The drug illustrated below: I Is primarily a Dz—Agonist. 11 Is metabolized to a—methylnorepinephrine. Ill Has been used as an antihypertensive agent. a I only b [11 only c I and [I only d II and 111 only I. II. and 111 Answer (7; l7. The drug illustrated below is: is administered orally. Inhibits the release of norepinephrine. is a Dl-receptor agonist. a I only b III only c I and I] only (1 II and III only 6 I. II, and 111 Answer 18. The drug illustrated below is: Is an angiotensin II receptor antagonist. Is used in the treatment of hypertension. Is a thiazide diuretic. a I only b III only c I and II only d II and 111 only e I. II. and III Answer 19. The drug illustrated below: (DQOO‘CD 20. 71. The dru illustrated below: (DD—00"” The dru illustrated below: 11 I Is a loop diuretic. II 15 used to treat congestive heart failure. [I] Is classified as Pregnancy Category D drug. [only 111 only I and II only 11 and III only I. II. and III Answer I Is used to treat Erectile Dysfunction. II Inhibits the enzyme HMG—COA reductase. III Lowers serum cholesterol. I only III only I and 11 only II and III only I. II. and III Answer I Has a metabolite that is active and has a longer duration of action. II Is used to treat Conn’s Disease. 111 Is an aldosterone receptor antagonist. I only III only I and 11 only II and III only I. II, and 111 Answer 7’) The drug illustrated below is: a I only b Ill only c I and I] only d 11 and 111 only e I, II. and III The drug illustrated below is: I only III only I and II only 11 and 111 only I. II, and III (DQOO‘QD The drug illustrated below is: a I only b III only C I and II only d 11 and 111 only e I. II. and III Used to treat Pulmonary edema. The most potent Loop diuretic. Used to treat Congestive Heart Failure. Answer Used to treat congestive heart failure. A phosphodiesterase inhibitor. Is eliminated via biliary excretion. Answer Is an hepatic enzyme inhibitor. Is a Class IB antianhythimc agent. I s a hepatic enzyme inducer. Answer 12 13 25. The drug illustrated below is: 9 S 9 A Thiazide diuretic. /S NHCCH U dt tre t Glaucoma. H N .V 3 se 0 a D 2 OK]; A carbonic anhydrase inhibitor. 3 I only b 111 only c I and 11 only d 11 and III only 6 I. II. and 111 Answer 26. The drug illustrated below is: A phosphodiesterase type 5 inhibitor. An angiotensen II receptor antagonist. A Pregnancy Category X drug. a I only b 111 only c I and [I only (1 II and 111 only 6 I, II, and III Answer 27. The drug illustrated below: I Is used to treat hypertension. II Is given iv as an antiarrhthymic agent. 111 Is a calcium channel antagonist. a I only b 111 only c I and II only (1 II and III only 6 I. II, and III Answer 14 Part Vll.(16 Points) Complete the stmctures of the FOUR following compounds 1. Benzenesulfonamide, 2-chloro-5-( l H—tetrazol-l —yl)-4—[(2-fiu'anylmethyl)amino)]- Ex) Piperidine. l-methyl-4-(5,6—dimethoxy-‘Z-quinazolinyl)- DJ 3-Acetoxy-2-bromo-2,3,3a,7,7a—hexahydro-lH-indole,2R(2a,3B,3aal7aa) or 3-Acetoxy-2-bromo-23,3a,7.7a-hexahydro-lH-indole, 2R(‘2R*,3R*,3aS*,7aS*) 4. N-[l—[(S)-3—Hydroxy-Q-mcthyl-1-ox0propyll-L-prolyl'l—L-valinc THERE ARE FIFTEEN PAGES IN THIS EXAM ! Part I 9 points P811 11 9 points Part III 12 points Part IV 54 points Part V m points 100 Points ...
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This note was uploaded on 04/14/2009 for the course 663 701 taught by Professor Arnold,e. during the Spring '09 term at Rutgers.

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mcI04e3 - Medicinal Chemistry I Examination Name _December...

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