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Medicinal Chemistry and Drug Design
MEDC 310
First Hour Exam
February 23, 2005
Name:____________________________ Pledge: _______________________
(All questions are 2.5 points unless otherwise stated.)
W.H. Soine
- The compound shown above is fluoxetine (Prozac™). Its approximate pKa would be:
A) -3 D) 9 B) 1 E) 13 C) 5
- Where will fluoxetine be best absorbed (the answer you give above will be used to determine the correct answer for this question):
A) Mouth (pH 6-7) B) Stomach (pH 1-3) C) Small Intestine (pH 7-7.5) D) Colon (pH 8) E) It is not absorbed when given orally
- The log P for t-butylbenzene is 3.81 (i) and for n-butylbenzene is 4.13 (ii).
Which compound is more lipophilic?
A) t-butylbenzene B) n-butylbenzene C) They are both equally lipophilic
CH (^3)
CH (^3)
CH (^3) CH (^3) i (^) ii
O NH
F 3 C
CH (^3)
- The following are the π values for various substituents on an aromatic ring: -CF 3 (1.07), -Br (0.94), -OCH 3 (-0.02), - CH 2 OH (-1.03). Which functional group listed above will increase the lipid solubility of the following drug the most (ie. we replace the R- group with one of the substituents).
A) -CF 3 (1.07) B) -Br (0.94) C) -OCH 3 (-0.02) D) -CH 2 OH (-1.03) E) They will all make the drug equally lipophilic
- The following is an enzyme (CYP2D6) that contains an aspartic acid side chain (ASP301) at its binding site. The figure is meant to depict methamphetamine at this binding site.
Identify the strongest and most important type of bonding force involved in this interaction.
A) reinforced ionic D) dipole-dipole B) ionic E) hydrophobic C) hydrogen
- What type of isomers are the following compounds:
A) Geometric Isomers B) Optical Isomers C) Configurational Isomers D) Conformational Isomers E) The same compounds
H^ N
CH 3
H
O
O
R
Methamphetamine ASP301 on CYP2D
Ph
H H
NHCH (^3) NHCH (^3)
H Ph
H
R
CH 3
H
CO 2 H
- Dragon’s Blood, which was being sold on the streets of Virginia as “red heroin” is an example of:
A) A material with unknown or unanticipated pharmacological effects. B) A new compound that will soon replace heroin on the “street”. C) A highly toxic drug. D) An extremely pure form of heroin. E) All of the above.
R.A. Glennon
- Between neurons, neurotransmission is:
A) from axon to dendrite C) from terminal to axon B) from dendrite to axon D) from axon to synapse
- Between neurons, neurotransmission is:
A) electrical C) mechanical B) chemical D) nonexistent
- Action of neurotransmitter can be terminated by:
A) release B) interaction with postsynaptic receptors C) biosynthesis D) reuptake
- Which of the following is an example of an autoreceptor:
A) somaotodendritic receptors C) serotonin receptors B) postsynaptic receptors D) transporters (e.g. SERT)
- Which of the following is least associated with G-protein coupled receptors:
A) seven transmembrane-spanning helicies B) activation of a second messenger system C) control of a ligand-gated ion channel D) neurotransmission
- Most neurotransmitters are biosynthesized in the neuron:
A) TRUE B) FALSE
- Each of the following represents a class of antipsychotic agents except:
A) thioxanthenes C) benzodiazepines B) butyrophenones D) phenothiazines
- Most antipsychotic agents:
A) act, at least in part, by blocking dopamine D2 receptors B) prevent symptoms of extrapyramidal stimulation C) are serotonin receptor agonists D) are useful for treating symptoms associated with anxiety
- Atypical antispychotics:
A) do not bind at dopamine receptors B) do not bind at serotonin (5-HT) receptors C) bind both at dopamine and serotonin receptors D) produce exaggerated extrapyramidal stimulation (EPS)
- Chronic administration of high doses of cocaine can mimic the symptoms of psychosis because:
A) it behaves as a releaser of dopamine B) it behaves as a releaser of serotonin C) it blocks the reuptake of dopamine D) it blocks the reuptake of serotonin
- Chronic administration of high doses of amphetamine can mimic the symptoms of psychosis because:
A) it behaves as a releaser of dopamine B) it behaves as a releaser of serotonin C) it blocks the reuptake of dopamine D) it blocks the reuptake of serotonin
- Identify the compound that is known as “XTC”(“Ecstacy”).
A) MDMA B) Methylenedioxymethamphetamine C) Cathinone D) DOM E) A) and B)
- (-)Cathinone is also known as
A) Ecstasy D) X B) Khat E) None of these C) Love Drug
- The drug discrimination procedure can be used to study
A) Stereoselectivity D) A) and C) B) Stereospecificity E) All of these C) Mechanism of Action
- Which statement(s) is(are) true?
A) S(+)-MDA is a hallucinogen B) R(-)-MDA is a stimulant C) R(-)-MDA is a hallucinogen D) A) and B) E) A) and C)
- Which statement(s) is(are) false?
A) The drug discrimination procedure can provide qualitative and quantitative information about a compound. B) Only stimulants and hallucinogens have been used in drug discrimination studies. C) Results from some drug discrimination studies have been shown to parallel(correlate) with human studies. D) All of the above E) B) and C)
L.B. Kier
- QSAR is
A) a synthetic method B) dependent upon crystal studies C) a modeling method D) an experimental method
- The biophase is
A) the liver B) the region of drug-receptor encounter C) the outcome of QSAR D) the region of excretion
- The receptor is
A) a feature on the drug molecule B) the entire drug molecule C) the measure biological response D) part of a macromolecule in the body
- The pharmacophore is
A) part of the drug moleecule B) the entire drug molecule C) the measure of drug activity D) a measure of biological response
- QSAR is
A) a model of the receptor B) a model of the pharmacophore C) a model of the structure D) a model relating activity with structure
- Some drugs are highly bound to plasma proteins particularly albumin. The binding to this protein is significantly decreased in patients with renal failure. Circle the best answer that will describe the outcome of this effect in a renal failure patient if they were to be administered a drug that is highly bound to albumin:
A) The patients should be given the same dose as for normal individuals. B) The patient should be given a higher dose than that given to normal individuals C) The patient should be given a lower dose than that given to normal individuals. D) The plasma concentration of the free (unbound drug) will be significantly lower compared to normal individuals. E) None of the above.
- Which of the following statement is incorrect:
A) The metabolism of drugs always increases biological availability of the parent compound. B) Phase II enzymes are usually conjugative enzymes. C) Oxidative metabolism is the major Phase I pathway that is responsible for removing substituents from functional groups. D) The liver is the major organ involved in drug metabolism. E) Some metabolism of drugs also occurs in the gut wall.
- Tylenol® overdosing can result in severe liver damage because:
A) The acetaminophen (Tylenol ®) is converted to a reactive oxidative metabolite. B) This reactive metabolite is rapidly detoxified by glutathione conjugation. C) The glutathione conjugates are readily excreted in the urine as harmless metabolites. D) At high doses the glutathione is depleted thereby enabling the reactive metabolites to attack nulceophilic macromolecules. E) Enzymes responsible for formation of reactive metabolites are induced.
