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203f01_e3_key - Chemistry 203 Lg(F 001)Exam#3 LastName ‘...

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Unformatted text preview: Chemistry 203 Lg (F 001)Exam#3 LastName: ‘ \ November 13, 2' ll; 11:00-11:50 am. . First Name: Professor C I les E. McKenna Social Security # T. -‘- I l ,; 4 INITIAL OF LAST NAME Please do not open this exam until yo ~ told to do so. I will observe the rules of Academic integrity while taking this exam. Student Signature Circle the most nearly correct answer. (4 Pts.) ‘ (1) Key goals of the medicinal chemist include: — Improving ease of administration of a drug - Reducing the side—effects of a drug - Increasing activity of a drug 0 All of the above (2) Development of a new drug based on a natural source includes the following steps: 1. Design/synthesis of improved novel drug structures 2. Screen natural sources for biological activity 3. Isolation of active compound from most active natural source. 4. Make structural analogs and determine structure-activity relationships. The logical order would be: - l, 3, 3, 4 — 3, 4, l, 2 @ 2,3,4,1 "' .29 39 1) 4 (3) Dr. Ebetino (Procter & Gamble guest lecturer) told us that osteoporosis: — Affects college-age men and menopausal women equally —- Has no effective drug treatment currently — Attacks all bone structures equally @ Can be treated by current drugs that block the activity of bone- ' dissolving cells (osteoclasts) i (4) (7) Drugs are mainly deactivated in the: , liver kidney lymph nodes bladder In general, drugs are deactivated in the body for excretion by: Conversion from polar to non-polar forms Changes like -CH3 -> -CH20H Changes like -CHZOH -> -CH3 Conversion to less water-soluble metabolites According to the “null hypothesis” in statistics, in a clinical drug trial: Control and drug groups should give identical results Any difference between control, drug groups is significant but psychosomatic in origin Any difference between control, drug groups can be explained as random ' Any difference between control, drug groups is significant and due to the drug A drug taken orally once daily, to be effective, must: resist stomach acid be absorbed by the gastrointestinal tract not be very rapidly metabolized all of the above are true (8) (9) A drug: _ ' i cannot be too hydrophilic needs a “+” or “—” charge to cross hydrophobic membranes cannot be too hydrophobic none of the above “is true One difference between pharmacokinetics (PK) and pharmacodynamics (PD): PD measures drug concentration in the blood PK measures drug toxicity PD measures drug clearance from the body PK measures bioavailability of drug administered Example of “synergism” in drug therapy: a drug that speeds up elimination of an antibiotic from the body by excretion a drug that speeds up metabolic breakdown of an anti-viral agent in the body a drug that reduces blood flow in an area where a local anesthetic has been administered, prolonging the numbing effect none of the above Suppose that in a clinical trial of a drug, we get a result for positive effect that is “borderline” significant. If we can raise $$ to repeat the study, we should aim to: Try lower doses of the drug Increase the number of subjects in the trial Increase the standard deviation of the trial results Decrease the value of “t” calculated from the trial results for the same number of subjects (12) Factors that could affect the proper drug dose for an individual include: — gender — weight — age @7 all of the above (13) Typically drugs bind to their receptor in their form. @ ionized non—ionized — demethylated — prodru g (14) In a typical QSAR graph, Log (1/C) refers to a drug’s — hydrophobicity — hydrophilicity — partition coefficient a biological activity (e.g., anti-viral activity) (15) An exercise science major plotted recent USC football victories vs.recent UCLA football victories; He fitted a regression line to his data that showed a negative correlation with R2 = 0.99: - these results establish a causal relationship between the two sets of data — the correlation is not highly significant because the regression coefficient is too low 0 these results indicate a highly significant correlation between the two sets of data but do not prove a causal relationship - causal relationship would be established, except that the regression coefficient is too low (16) Taking “Cipro”, Bayer’s antibiotic as a precaution “just in case" of an exposure to anthrax is probably not a good idea because: - This drug can have unpleasant side effects — The odds of exposure are extremely low - Unnecessary use of antibiotics may lead to resistance in other diseasecausing bacteria @ Of all the above (17) An offshore drug company weighs an anti-anthrax drug into capsules carelessly, such that the average amount of drug/capsule is 150.0 mg with a standard deviation f: :45 mg. It v k/is1'iown that double the normal dose causes memory loss. Given the following data: 2 = / 2.5, p = 0.01; z = 3.0, p = 0.002; 2 = 3.3, p = 0.001, if 20,000 patients take this drug once, how many are likely to suffer memory loss because randomly their pill happened to centain twice the correct dose? (remember that z = (u—x—baryo) ‘ ... 0 .— [3'0 — all (WK 7” 1’0 N 3 I09 — about 250 , Hf r 21 ’2"); ID‘ I; a about 20 - ’- “ / ' none Z 0 (18) According to the diagram, modification of the neurotransmitter drug shown to prevent bond rotation will : 9 Likely increase selectivity by restricting binding to only one of the two receptors — Likely decrease selectivity by restricting binding to only one of the two receptors - Facilitate binding to both receptors _ - Prevent H-bonding interactions between the drug OH group and the receptor OH group (19) Consider the following diagram: — The inhibitor binds only to free enzyme, changing the maximal velocity (rate), Vm ( — J The inhibitor binds only to free enzyme, changing the Michaelis—Menten constant, Km — Adding more substrate (S) has no effect on the Velocity (V) — Adding more inhibitor (1) will have! no effect on the velocity +8 EMESME+P “ll El + Competitive 9 1/13} (20) A new clinical trial tested the drug MDTA, “ecstasy” for effectiveness against post- traumatic stress syndrome. The mean level of symptoms in a large group of untreated patients is known, u = 8.0. For the drug-treated group ‘(10 patients), the average level (x-bar) is found to be 4.2, with sample standard deviation (8) = 3.6. Given that t = (u - x-bar)/(an), use the probability table shown (top of next page) to select the probability that the drug worked: _ 99% C <¢~43 __ 3g '9 “8‘8 sags ‘ H N (c 1.9 g '/z 3'? e T?) W115 Wpoinzs to: we r dismion MI- 3 Area tome ugh! 089296: of m» - m l 2222 127% j 32%: 632%? 2 2.229 2,222 ’ 5.9% 9228 ,. \ 2 2:22 2,222 4522 5222 V\ .2: » , 2.222 2222 3222 22822 2 22:2 2522 . 22% 2022 ~6 2,923, 2,227 2 3.123 3.237 7 18% 2m 29% 3.293 2. 3 ml ‘ m was 9" was 2.222 2 2m 2221 . =2. 12 2222' , 2223 2.252 t (21) “Placebo effect” refers to: - Patients showing a real positive effect from a drug — Patients showing a real negative effect from a drug Patients showing an apparent positive effect from an inactive starch tablet — Patients asking for more drug (Latin, “1 shall (be) please(d)”) (22) The diagram shows : — Deactivation of a toxic anti-anthrax drug — Synthesis of a relish often used with hot dogs Conversion of a nontoxic anti-cancer prodrug to its toxic, active form —- Conversion of a nontoxic anti-alcoholism prodrug to its toxic, but active form (23) QSAR means: a Quantitative Structure-Activity Relationships — Qualitative Structure-Activity RelationShips —- Qualified Structure-Activity Relationships — Quantitative Stereochemical Association Ratio (24) Examples of drug metabolic reactions include: — Hydrolysis of esters and amides — Conversion of L-Dopa to dopamine — Loss of methyl groups CH3 from N—CH3 groups in a drug fl All of the above (25) Thediagram illustrates: A substrate binding via Van der Waals, H—bonding and ionic interactions to a rigid enzyme active site, like a key into a lock 0 A substrate binding via Van der Waals, H-bonding and ionic interactions to a flexible enzyme active site, inducing a better fit - A substrate binding via ionic interactions to an enzyme active site, like a key into a lock — Inactivation of an enzyme by an irreversible inhibitor BONUS QUESTIONS! (plus 8 points) (22) Consider the goat-car probability problem, with 3 goats and 1 car, 4 doors. You pick a door, Vanna White opens another door to show you a goat. What are the odds of getting the car if you always switch to one of the other two doors? Is this still better than sticking with your original door? Explain. ‘ 015% MW fle 6M] (<1: 445cc? ‘/‘1 c, s y ‘ ?1J’ o. A. 'I 3 (f 56442,. qurngu/ixw 'go sMW'y?) Va W48Véhb’w 3/,, x i = 7/7 w/ W dé.’ n willy. 2) Give two reasons [email protected] a bigger threat to us than anthrax, as a bioterrorisrn vector. i) M L 0”“ '{7 64‘ “4/1 Winfi- wfim W W Maw 10 ...
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