Deck 10: Manipulating Molecules and Designing Drugs

Question 1

Which pair represents isomers?

A)
B)
C)
D)

Answer 1

Question 2

What is the structure of the ester that is formed in the following reaction?

A)
B)
C)
D)

Answer 2

Question 3

This is the condensed structural formula for acetaminophen,the active ingredient in the over-the-counter medication Tylenol.What is the molecular formula of acetaminophen?

A)C₈H₅NO₂
B)C₈H₁₁NO₂
C)C₈H₉NO₂
D)C₈H₈NO

Answer 3

C₈H₉NO₂

Question 4

Which functional group contains a nitrogen atom?

A)alcohol
B)amine
C)ester
D)ether

Question 5

Which statement related to the "wonder drug" aspirin is not true?

A)The folk remedy using a tea made from willow bark ultimately led to the discovery of aspirin as we know it today.
B)A rare,but life-threatening,side effect of aspirin is blood in the urine.
C)Aspirin inhibits the clotting of blood and commonly causes some stomach bleeding.
D)Aspirin selectively blocks the COX-2 enzyme but does not block the COX-1 enzyme.

Question 6

Isopentyl acetate (shown here)is used as a flavoring agent in food.Its fragrance is that of bananas.What functional group(s)is(are)present in this compound?

A)ester only
B)ketone only
C)ketone and ether only
D)ester,ether,and ketone

Question 7

For this line-angle drawing,which condensed structural formula is correct?

A)CH₃CH₂CH₂CH₂OH
B)CH₃CH(CH₃)CH₂OH
C)CH₃CH(OH)CH₂CH₃
D)CH(CH₃)₂CH₂OH

Question 8

Isomers are compounds that have

A)the same chemical formulas and molecular structures but different physical properties.
B)the same chemical formulas but different molecular structures and physical properties.
C)different chemical formulas and molecular structures but the same physical properties.
D)different chemical formulas,molecular structures,and physical properties.

Question 9

This is the carbon skeleton for one of the isomers of heptane,C₇H₁₆,with the hydrogen atoms omitted.Which structure is not an isomer of the structure shown?

A)
B)
C)
D)

Question 10

Which is not caused by prostaglandins?

A)fever and swelling
B)increased rate of metabolic reactions
C)increased sensitivity of pain receptors
D)inhibition of blood vessel dilation

Question 11

Amino acids are compounds that contain both amine and organic acid functional groups.Which compound is an amino acid?

A)
B)
C)
D)

Question 12

In carbon containing compounds,carbon usually forms

A)four bonds,nitrogen usually forms three bonds,oxygen usually forms two bonds,and hydrogen only forms one bond.
B)four bonds,nitrogen usually forms five bonds,oxygen usually forms six bonds,and hydrogen only forms one bond.
C)four bonds,nitrogen and oxygen usually form two bonds,and hydrogen only forms one bond.
D)three bonds,nitrogen and oxygen usually form two bonds,and hydrogen only forms one bond.

Question 13

For n-hexane,C₆H₁₄,which molecular representation is correct?

A)
B)
C)
D)

Question 14

Which is the carbon skeleton of an isomer of the compound shown?

A)
B)
C)
D)

Question 15

The father of modern medicine,Hippocrates,described making a tea that was effective against fever by boiling willow bark.Years later,the active ingredient was isolated and chemically modified to produce the drug we now know as

A)acetaminophen.
B)aspirin.
C)ibuprofen.
D)penicillin.

Question 16

This is the carbon skeleton for a structural isomer of octane with the hydrogen atoms omitted.What is the molecular formula of this isomer?

A)C₈H₈
B)C₈H₂₄
C)C₈H₁₇
D)C₈H₁₈

Question 17

The common OTC medication ibuprofen is sold as a racemic mixture although only the L-isomer is a pain reliever.What does the term "racemic mixture" mean?

A)There is an equal mixture of the D- and L-optical isomers in the drug preparation.
B)There are two active ingredients in the drug preparation.
C)The inactive optical isomer does not cause serious side effects.
D)The inactive isomer is transformed into the active isomer in the body.

Question 18

Why are many drugs administered as salts rather than as the corresponding neutral compounds?

A)Salts have greater water solubility and stability than the neutral compound.
B)As a general rule,salts are more active than the neutral compounds.
C)Salts are generally liquid and therefore more active than the neutral compounds.
D)The salts are less expensive to produce than the corresponding neutral compounds.

Question 19

The octet rule is applied to bonding in carbon containing compounds.In accordance with the octet rule,

A)each bonded carbon atom forms eight bonds.
B)all carbon containing compounds contain at least eight bonds.
C)each bonded carbon atom shares electrons so that it has exactly eight outer shell electrons.
D)the number of atoms in any carbon containing compound is a multiple of eight.

Question 20

Which functional group does this molecule contain?

A)acid
B)alcohol
C)amine
D)ester

Question 21

Which is not an example of an over-the-counter medication?

A)cough suppressants,such as dextromorphan.
B)antacids and indigestion aids,such as calcium or magnesium salts.
C)anti-anxiety drugs,such as valium.
D)motion sickness drugs,such as diphenhydramine.

Question 22

Compounds that reduce fever are called _____;compounds that reduce pain are called ____.

A)analgesics;antipyretics
B)analgesics;hormones
C)antipyretics;analgesics
D)antipyretics;prostaglandins

Question 23

Which statement best describes the functions of the COX-1 and COX-2 enzymes?

A)COX-1 primarily makes hormones that maintain proper kidney function and repair the stomach lining while COX-2 makes prostaglandins associated with inflammation,pain,and fever.
B)COX-1 makes prostaglandins associated with inflammation,pain,and fever while COX-2 primarily makes hormones that maintain proper kidney function and repair the stomach lining.
C)COX-1 primarily makes steroids related to secondary sexual characteristics while COX-2 makes prostaglandins associated with inflammation,pain,and fever.
D)COX-1 makes NSAID drugs associated with inflammation,pain,and fever like ibuprofen and aspirin while COX-2 primarily makes hormones that maintain proper kidney function and repair the stomach lining.

Question 24

Which phrase best describes the function of the steroid progesterone?

A)regulates secondary sexual characteristics
B)controls the female reproductive cycle
C)regulates fat metabolism
D)is a cell membrane component

Question 25

The family of compounds known as steroids share a common molecular framework of 17 carbon atoms that are arranged into four rings.Which is a representation of this common molecular framework?

A)
B)
C)
D)

Question 26

Which of these incorrectly pairs a hormone with its function?

A)thyroxin-regulates metabolism
B)insulin-enables the body to use glucose (blood sugar)for energy
C)adrenaline (epinephrine)-prepares the body to "fight or flee"
D)progesterone-controls muscle mass

Question 27

Which compound cannot exist as a pair of optical isomers?

A)
B)
C)
D)

Question 28

Although all aspirin tablets contain the same active ingredient,acetylsalicylic acid,not all aspirin tablets are the same.Which is not a possible reason for this difference?

A)They contain fillers and bonding agents that may vary,depending on the manufacturer.
B)Some may contain weak bases that act as buffers to reduce the natural acidity of the aspirin.
C)Some may be coated to keep them intact until they reach the intestine.
D)Some may contain the inactive optical isomer in the preparation.

Question 29

Enzymes are

A)biochemical catalysts that influence the rate of metabolic reactions.
B)compounds used to relieve inflammation in muscles and joints.
C)proteins that produce fever and swelling.
D)special hormones that influence the rate of metabolic reactions.

Question 30

Which is not true concerning the discovery and development of the penicillin antibiotics?

A)Alexander Fleming noted that the mold Penicillium notatum inhibited bacterial growth.
B)The first step in the development of these drugs was the isolation of the active agent produced by the mold Penicillium notatum.
C)There are currently more than a dozen different penicillins in clinical use.
D)World War I gave added impetus for the development of the penicillin antibiotics.

Question 31

This is the structure of the steroid known as

A)cholesterol (single alcohol functional group).
B)cortisone (multiple alcohol and ketone functional groups).
C)estradiol (has multiple alcohol functional groups).
D)testosterone (one alcohol and one ketone functional group).

Question 32

The body's chemical messengers,called _____,are produced in the endocrine glands.

A)enzymes
B)hormones
C)isomers
D)viruses

Question 33

Which phrase best describes the function of the steroid testosterone?

A)regulates secondary sexual characteristics
B)controls the female reproductive cycle
C)regulates metabolism
D)regulates digestion of fat

Question 34

What structural feature do the two hormones shown have in common?

A)Both have alcohol functional groups.
B)Both have ketone functional groups.
C)Both are steroids.
D)There are no structural features in common.

Question 35

This is the structure of pseudoephedrine.Which is the correct structural formula for the hydrochloride salt of pseudoephedrine?

A)
B)
C)
D)

Question 36

A pair of chiral (optical)isomers has different

A)boiling points.
B)interactions with polarized light.
C)melting points.
D)molar masses.

Question 37

The term "pharmacophore" was originally described by the Nobel Prize winner Paul Ehrlich more than 100 years ago.What is the meaning of this term?

A)the correct dose at which a drug should be administered
B)the three dimensional arrangement of a drug responsible for its biological activity
C)the form in which a drug is prepared for oral consumption
D)the group of compounds responsible for euphoria

Question 38

The diagram shows a cartoon describing the lock and key model of biological interactions.What do A and B represent?

A)A represents an enzyme and B represents a drug or hormone.
B)A represents a drug or hormone and B represents an enzyme.
C)A represents a drug or hormone and B represents a cell membrane receptor site.
D)A represents a cell membrane receptor site and B represents a drug or hormone.

Question 39

Identify the chiral carbon atom in L-dopa (used to treat Parkinson's disease).

A)1
B)2
C)3
D)4

Question 40

What functional groups are common to both ibuprofen and dopa?

A)acid
B)alcohol
C)amide
D)amine

Question 41

What herb is used to treat depression?

A)chamomile
B)ginko biloba
C)lemon balm
D)St.John's wort

Question 42

Which incorrectly pairs over-the-counter drugs with its target function?

A)aspirin-anti-inflammatory agent
B)dextromorphan-cough suppressant
C)ibuprofen-antacid
D)pseudoephedrine-decongestant

Question 43

Which of the following statements is not true?

A)The generic version of a drug is usually less expensive than the original version.
B)The generic version of a drug cannot be marketed until the patent protection on the pioneer drug has expired.
C)Generic drugs do not have to duplicate the efficacy and safety testing required of the counterpart pioneer drug.
D)The FDA requires that the generic drug be bioequivalent to the pioneer drug;that is,it should deliver the same amount of active ingredient into a patient's bloodstream at the same rate.

Question 44

When drug researchers talk about nanoscale technology,what does this mean?

A)a size domain less than 100 mm
B)a size domain between 1 and 100 nm
C)the number of possible drug interactions being greater than 1 × 10⁹
D)the number of possible drug precursors being greater than 1 × 10⁹

Question 45

Which statement related to OxyContin is not correct?

A)OxyContin is the trade name for the drug oxycodone hydrochloride,a morphine-like narcotic.
B)OxyContin should be taken orally,however abusers crush the tablet and snort it or dissolve it in water and inject it.
C)OxyContin is a Schedule I drug under the Controlled Substances Act because of the high risk of addiction and abuse.
D)OxyContin is referred to as "hillbilly heroin" or "poor man's heroin" because problems of abuse were first noted in Kentucky,Virginia,West Virginia,and Maine.

Question 46

What herb is used to reduce memory loss?

A)chamomile
B)ginko biloba
C)lemon balm
D)St.John's wort

Question 47

Which of the following statements is true?

A)Over-the-counter (OTC)drugs are not screened by the FDA.
B)More than 700 OTC products were once only available by prescription.
C)Drug manufacturers are against switching a prescription drug to OTC status.
D)Only NSAIDS can switch to OTC status.

Question 48

In drug research,the term "double blind testing" is often used.What does this mean?

A)The patients don't know if they are in the experimental or control group.
B)The physicians don't know which patients are in the experimental group.
C)The patients and the physicians don't know who is in which group.
D)The patients and the physicians only know who is in the control group.

Question 49

Which statement related to marijuana is not correct?

A)The first recorded use of marijuana was to treat malaria,gas pains,and absent mindedness in 2737 BC in China.
B)Marijuana is the second most used illicit drug in the United States,with common (slang)names such as pot,weed,grass and Mary Jane.
C)George Washington kept a field of hemp at Mt.Vernon and he is believed to have used the hemp for rope and medicine.
D)In 1942 marijuana was removed from the U.S.Pharmacopeia because it was believed to be harmful and addictive.

Question 50

Which statement is not true?

A)From discovery to approval,the development of a new drug takes,on average,two years and $500,000.
B)The most controversial toxicity testing involves the determination of the lethal dose-50 (LD-50),the minimum dose that kills 50% of the test animals.
C)Clinical testing of drugs on humans cannot begin before the FDA has examined the results of the tests on animals.
D)The primary goal of the FDA is to establish whether a drug is effective and safe before it is sold to the public.

Question 51

Which region of cholesterol is most responsible for its solubility in nonpolar substances?

A)Region 1
B)Region 2
C)Region 3
D)Region 4

Question 52

Which statement is not true?

A)Herbal remedies and folk medicines abound in most cultures.
B)Most compounds found in plants are likely to have positive physiological effects in humans.
C)A preparation of St.John's wort is believed to be an effective treatment of depression.
D)A major problem with herbal preparations is that no regulatory group controls the purity of the preparations and the concentrations of the active ingredients.

Question 53

The steroid cholic acid is more soluble in water than most other steroids.Based on your understanding of the solubility of molecular compounds in water,decide which compound is cholic acid.

A)
B)
C)
D)

Question 54

Why are generic versions of some prescription drugs not always available?

A)The prescribed drug may still be protected by the 20-year patent.
B)The prescribed drug may be derived from a common herb.
C)The drug company that developed the drug has not agreed to allow other companies to make the drug.
D)The manufacturers of generic drugs have not completed the efficacy and safety testing of the generic drug.

Question 55

Comparing the structures of aspirin,ibuprofen,and acetaminophen,what do they have in common?

A)acid functional groups
B)amide functional groups
C)benzene rings
D)ester functional groups

Question 56

Which statement about cholesterol is not true?

A)Cholesterol is the most abundant steroid in the body.
B)Cholesterol is the starting point for the synthesis of many steroid-related hormones.
C)Cholesterol is essential for life;the average human has 0.5 lb of cholesterol in his/her body.
D)The only way to reduce blood levels of cholesterol is to eat cholesterol-free foods.

Question 57

What is meant by a "citizen petition"?

A)It alerts the FDA to a safety issue surrounding a drug.
B)It asks the FDA to make a prescription drug available over-the-counter.
C)It asks the FDA to force a drug company to make a generic drug.
D)It demands the FDA to "fast-track" a drug's approval.

Question 58

Which of these are not yet used in drug delivery systems?

A)bio-nanotubes
B)carbon nanotubes
C)ceramic microstructures
D)microtubes

Question 59

Which incorrectly pairs the common herb with its target function?

A)ginko biloba-inhibits memory loss
B)passion flower-relieves anxiety
C)St.John's wort-lessens depression
D)thyme-eases symptoms of colds and flu

Question 60

This is the structure of the steroid known as

A)cholesterol.
B)estradiol.
C)progesterone.
D)testoseronel.

Question 61

Of the following,which may be removed from the market only when the US government can prove harm?

A)Prescription drugs
B)Over the counter drugs
C)Herbal remedies
D)All of the above

Question 62

The FDA regulates

A)prescription and over-the-counter drugs.
B)herbal remedies.
C)only over-the-counter drugs.
D)toxic chemicals in consumer products.

Question 63

Which category of drugs of abuse has the smallest population of users in the US?

A)Hallucinogens
B)Marijuana
C)Stimulants
D)Pain killers

Question 64

Which is not a common over-the-counter drug category?

A)Anti-inflammatory
B)Antacid
C)Antihistamine
D)Stimulant

Question 65

Morphine,opium and oxycodone are what in what "drug schedule"

A)I
B)II
C)III
D)IV

Question 66

What is one method employed to keep a drug under patent and out of reach of generic drug manufacturers?

A)One optical isomer in a racemic mixture is isolated and packaged alone.
B)A new name is placed on a older drug.
C)New fillers are added to the old mixture replacing the previous recipe.
D)Functional groups are changed on the original drug molecule.

Question 67

Which of the following is true of the green by design process Codexis used to create HN?
I.There is less waste.
II.Harsh reagents are avoided.
III.It uses recombinant technology.
IV.It needs intense purification.

A)I and IV only
B)II and III only
C)III and IV only
D)I,II,and III only

Question 68

To what chemical receptor do the opiate drugs bind?

A)alpha
B)delta
C)mu
D)omega

Question 69

Concerning dietary supplements,which of the following statements is true?

A)They are not reviewed by the FDA before they are marketed.
B)They are classified as "food and drugs."
C)They are assessed for purity by the DSHEA before they are marketed.
D)They are required not to interact with traditional medicines.

Question 70

Identify groups of structural isomers among the compounds below:

A)3 and 5 AND 1 and 4
B)2 and 3
C)1,3 and 5
D)1 and 4