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Unformatted text preview: Chemistry 203 Lg (Fall 2004) Exam #3 Last Name: ‘6’ f @ , November 9, 2004; 11:0011:50 am. First Name: Professor Charles E. McKenna Social Security # T.A: FM Please do not open this exam until you are told to do so.
Write legibly to avoid confusion.
GOOD LUCK ! ! Student Signature Which reaction metabolizing a drug is not likely to happen?
RCOZR 9 R~C02H + ROH
RN(CH3)29 RNH2 R—CH3 9 RCHZOH
R—OH —> RCH3 The most important region of the GI tract for drug absorption is usually the?
Stomach Esophagus
Lungs Intestine Comparing pharmacokinetics (PK) and pharmacodynamics (PD):
PK measures drug efﬁcacy PK measures drug concentration in the blood
PD measures bioavailability of drug administered PD measures drug clearance from the body The diagram below shows: Synthesis of a relish often used with hot dogs Deactivation of a toxic antianthrax drug Conversion of a nontoxic antialcoholism prodrug to its toxic, active form Conversion of a nontoxic anti—cancer prodrug to its toxic, active form MO 0, \
Ho’ PfN/ Cl C!
CYCLOPHOSPHAMIDE PHOSPHORAMIDE MUSTARD 5. Consider Bayes’ theorem applied to a “five doors” version of the car—goat problem
discussed in class. I select a door; I’m shown a goat behind another door. The odds of getting the car are _ if I stand pat and __ if I choose a different door:
— 1/5 1/3
— 1/5 1/4
0 1/5 4/15
— 1/5 1/5
6. Key goals of medicinal chemists include: — Improving ease of administration of a drug
 Reducing the sideeffects of a drug
— Increasing drug efficacy g All of the above 7. Dr. Ebetino (guest lecturer) told us that osteoporosis:
— Has no effective drug treatment currently
— Involves a receptor called melanocortin 4 — Can be treated by current drugs that block pyrophosphate uptake into bone 0 Attacks trabecular bone structures 8. Drugs are mainly deactivated in the:
— 7 kidney
Q liver
— bladder
— lymph nodes
9. According to the “null hypothesis” in statistics, in a clinical drug trial:  Any difference between control, drug groups is significant but psychosomatic in origin
— Control and drug groups should give identical results — Any difference between control, drug groups is significant and due to the drug
6 Any difference between control, drug groups can be explained as random 10. 12. Degrees of
freedom. I! d  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:
Increase the number of subjects in the trial Try lower doses of the drug Decrease the value of “t” calculated from the trial results for the same number of subjects
Increase the standard deviation of the trial results In a typical QSAR graph, Log (1/C) refers to a drug’s:
Hydrophilicity Hydrophobicity Biological activity (e. g., anti—viral activity) Partition coefficient A new clinical trial tested MDMA, “ecstasy” for effectiveness against posttraumatic stress
syndrome. The mean level of symptoms in a large group of untreated patients is known, it =
7.0. For the drugtreated group (9 patients), the average level (xbar) is found to be 4.0 with
sample standard deviation (5) = 2.68. Given that t = (pi — x—bar)/(s/\/n), use the probability
table shown below to select the probability that the drug worked: 97.5% 99% 100% 99.5% /Am ommumwme—a 13. Typical drugs that have an ionized (charged) form in equilibrium with nonionized
(uncharged) forms cross cell membranes in their form and bind to their
receptor in their form. — Ionized, non—ionized @ Nonionized, ionized — Acid, basic
— Stable, unstable °§ P"
P‘mH OH
O (fa—0H OH Risedrnnate
14. The drug shown above is primarily used to treat:
 Obesity — HIV infection — Thyroid cancer 0 Osteoporosis 15. When I test a drug for biological activity using a computer model, I am conducting the
test: 0 In silico
— In vivo
— In vitro — In laboratorio 16. In bone metabolism, specialized cells, that bone structure, are targets of bisphosphonate drugs. 9 Osteoclasts, dissolve
Osteoclasts, rebuild — Osteoblasts, dissolve
— Osteoblasts, rebuild L08 (I/C) “’3” Log? (1) = —k1(logP)2 + k2 logP + k3.
log 5 17. For the graph above, the corresponding equation is indicated. If k3 = 0, then for a drug
giving the point “+” shown:
— The (log P) term dominates the (log P)2 term 9 The (log P)2 term dominates the (log P) term
— The (log P)2 term balances the (log P) term — The drug is too hydrophilic 18. Osteoporosis typically affects: — Women under 50, men over 90 — Women during and after menopause, men under 60
y Women during and after menopause, men at 75 and older — Women after 30, men after 50 19. Calculations on a drug’s pharmacological properties address its:
— Distribution  Excretion — Adsorption a All of the above 20. A very lipophilic drug “A” is added (with stirring) to a mixture of n—octanol (CH3(CH)6
CHZOH) and water: — We will get a homogeneous solution — The drug will mostly partition into the lower, aqueous layer @ The drug will mostly partition into the upper, noctanol layer
— The drug will substantially partition into both layers, but mostly into the
lower n—octanol layer Drug solubility and drug dissolution: Rate of dissolution is proportional to the difference between the amount dissolved (“concentration”), and the maximum solubility (saturating
concentration) — Solubility 2 rate at drug dissolves — Dissolution = amount of drug dissolved
— All of the above are true 22. QSAR is:
— Quantitative solubilityabsorption ratio
— Qualitative structure—activity relationship — Quantitative solubilityactivity ratio
a Quantitative structureactivity relationship 23. A drug activity result is 2 standard deviations (20) away from the average result. The probability that the observed difference is purely by chance is:
— 5% — 0.5%
— 35% 24. A plot of QSAR data shows a linear regression (r2) value of 0.6 with a slope of 2. The
correlation is: — Positive, very significant — Negative, very significant 6 Positive but very weak — Negative but very weak 0 HZN C— 0"“ CHQCHQNEtz PROCAINE 25. The two drugs shown above are both dental anesthetics, but have different
pharmacological properties.
— Procaine has a more prolonged effect
@ Lidocaine’s two CH3 groups slow down its breakdown after injection
— Procaine is less easily metabolized in the body and excreted
— Lidocaine’s NHCO bond is much more rapidly cleaved by cellular enzymes
than the COO bond of procaine L/ .‘ W W 4": ’2“ Mi. "(WIW a» v
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K bujfﬂéé' W04M7 (“"Z“ ' "7‘ 4 («ow: ‘ BONUS UESTION DO EITHER ONE ~— YOUR CHOICE — FOR TO L OF 4 BONUS p 4 an» 4/ 1. (4 Points) The Chevalier de Mere s s to Blaise Pascal, “Here’s my bet. I throw one die. If I ...
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 Fall '07
 Mc Kenna
 Chemistry, Pharmacology, Medicinal Chemistry, Solubility, Quantitative structureactivity relationship, Partition coefficient

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