Chapter 31

Organic Chemistry, 6e (Bruice)Chapter 31 The Organic Chemistry of Drugs

1) Which of the following terms is (are) synonymous with the term "proprietary name?"A) generic nameB) trademarkC) trade nameD) brand nameE) both C and DAnswer: ESection: 31-1

2) The ________ name of a drug is the name that any pharmaceutical company can use to identify the drug.Answer: genericSection: 31-1

3) In pharmaceutical research, what is a "lead compound"?Answer: A lead compound is a pharmaceutically active compound of known structure which is used as the prototype in a search for other, structurally similar, active compounds.Section: 31-2

4) In pharmaceutical research, explain what is meant by "molecular modification."Answer: Molecular modification is the process through which analogs of the lead compound are synthesized by altering its structure (changing functional groups, ring sizes, chain lengths, etc).Section: 31-2

5) What compound served as the lead compound in the research which developed today's most commonly utilized local anesthetics?A) morphineB) cocaineC) codeineD) sulfanilamideE) nitroglycerinAnswer: BSection: 31-3

6) What compound is the most widely used analgesic for severe pain?A) LibriumB) dextromethorphanC) AtivanD) BenadrylE) morphineAnswer: ESection: 31-3

1Copyright © 2011 Pearson Education, Inc.

7) Novocain and Xylocaine are two compounds which are commonly used as local anesthetics. The structures of these two drugs are similar, but where Novocain has an aromatic ester functionality, Xylocaine has an aromatic amide group. Which of these drugs has a longer lifetime in the body and why?Answer: Xylocaine has the longer lifetime because amides are slower to hydrolyze than esters.Section: 31-3

8) Based on the structures of morphine, codeine, and heroin, explain why heroin is the most rapid acting member of the opiate family.Answer: Because heroin is less polar than morphine or codeine, it crosses the blood-brain barrier more rapidly and results in a more rapid physiological response.Section: 31-3

9) What is the name of the receptor in the central nervous system which binds morphine and codeine?Answer: the opiate receptorSection: 31-3

10) Why does injecting a mixture of epinephrine and Xylocaine give a more prolonged anesthetic effect than does injecting Xylocaine alone?Answer: Because epinephrine is a vasoconstrictor, it reduces the blood supply to the injected area. This allows the Xylocaine to remain in the injected area for a longer period of time.Section: 31-3

11) List 3 members of the opiate family, and give the main reason for their prescription by physicians.Answer: morphine, codeine, dextromethorphan, etorpine, pentazocine; their major use is as pain killers or analgesicsSection: 31-3

12) Identify the pharmaceutical compound below, and state how it's used as a drug.Answer:

Benzocaine; topical anestheticSection: 31-3



morphine; analgesicSection: 31-3

14) Who is credited with carrying out the first blind screen in his search for a "magic bullet" to cure African sleeping sickness?A) Jonas SalkB) Louis PasteurC) Edward JennerD) Paul EhrlichE) Gerhard DomagkAnswer: DSection: 31-4

15) An important part of a random screen is the recognition of effectiveness in the compounds screened. What term is used to identify the test by which effectiveness is measured?A) assayB) dissolutionC) modelingD) combinatorial analysisE) synergismAnswer: ASection: 31-4

16) What term is used to describe a screening test which is conducted outside the body, in a test tube for example?A) in totoB) in tuboC) in vitroD) in locoE) in vivoAnswer: CSection: 31-4


17) What term describes a drug that, once taken, inhibits further growth of bacteria?A) generic drugB) bacteriostatic drugC) antiviral agentD) vasodiolation agentE) bactericidal drugAnswer: BSection: 31-4

18) What gave scientists the idea that azo dyes might be candidates as antibacterial agents?Answer: The fact that these dyes bound to wool fibers which are composed of protein led scientists to speculate that they might also bind to bacterial proteins.Section: 31-4

19) Prontosil, a bright red dye, was an active antibacterial agent in vivo but not in vitro. Scientists also noted that mice given Prontosil did not excrete a red compound. What possible explanation of the activity of Prontosil is consistent with these two observations?Answer: The dye is converted into an active, but noncolored, compound via some metabolic process of the mouse.Section: 31-4

20) Which of the following drugs is a member of the benzodiazepine family?A) nitroglycerinB) acetylcholineC) morphineD) penicillinE) LibriumAnswer: ESection: 31-5

21) Which of the following drugs, discovered serendipitiously, is known to relieve angina pectoris by dilating cardiac blood vessels?A) nitroglycerinB) morphineC) acyclovirD) sulfanilamideE) LibriumAnswer: ASection: 31-5


nitroglycerin; vasodilatorSection: 31-5



Valium; tranquilizerSection: 31-5

24) What name is given to the receptors involved in neurotransmission, memory, and wakefulness?A) cholinergic receptorsB) beta-blockersC) histamine receptorsD) prostaglandin receptorsE) opiate receptorsAnswer: ASection: 31-6

25) Which of the following drugs does not contain a heterocycle as part of its structure?A) BenadrylB) LipitorC) PrilosecD) MorphineE) LibriumAnswer: ASection: 31-6

26) Which of the following compounds was used as a lead compound in the development of antiulcer agents?A) penicilloic acidB) cocaineC) heroinD) 4-methylhistamineE) β-lactamaseAnswer: DSection: 31-6



chloroquine; antimalarialSection: 31-6


Benadryl (diphenhydramine); antihistamineSection: 31-6


Tagamet (cimetidine); antiucler (inhibits HCl secretion)Section: 31-6



Imitrex; antimigraineSection: 31-6

31) What term is given to the specific cellular binding site with which some drugs interact to trigger their physiological effect?Answer: receptorSection: 31-6

32) What structural feature do most effective antihistamines have in common with histamine and how is this common feature believed to be related to the effectiveness of antihistamines as drugs?Answer: Like histamine, antihistamines have a protonated amino group at the end of an alkyl chain which allows these compounds to bind to a negatively charged portion of the histamine receptor. Antihistamines thus bind to the histamine receptor and prevent histamine from doing so.Section: 31-6

33) Provide the structure of histamine, and predict the most likely charge of the histamine receptor. Answer: Since histamine itself is positively charged, the histamine receptor is most likely negatively charged.

Section: 31-6

34) With what other receptor does the histamine receptor show overlapping activity? Give an example.Answer: The histamine receptor shows overlap with the cholinergic receptor. This is why the antihistamine diphenhydramine has been used to treat insomnia and to combat motion sickness.Section: 31-6


35) What type of enzyme is secreted by penicillin resistant bacteria which hydrolyzes penicillin before it has an opportunity to interfere with cell wall synthesis?A) esteraseB) β-lactamaseC) proteaseD) oxidaseE) reductaseAnswer: BSection: 31-7

36) What new functional group is introduced to the penicillin structure when it is converted to a derivative by the oxidizing agent MMPP?A) N-oxideB) oximeC) sulfoneD) amideE) carboxylic acidAnswer: CSection: 31-7

37) What term is given to the effect which results when two drugs are used in combination and a response greater than the sum of the drugs' individual effects is observed?A) additiveB) combinatorialC) distributiveD) synergisticE) antagonisticAnswer: DSection: 31-7

38) Name the last major class of antibiotics which were discovered. Members of this family work by inhibiting an enzyme required for transcription in bacteria.A) sulfa drugsB) cephalasporinsC) tetracyclinesD) fluoroquinolonesE) penicillinsAnswer: DSection: 31-7

39) Which of the following reagents could be used to produce a sulfone from penicillin?A) CH3CO3HB) Zn, HClC) Raney NiD) H3O+

E) none of the aboveAnswer: ASection: 31-7


40) If we have a variety of effective antibiotics, why do pharmaceutical companies continue to search for new ones?Answer: Bacterial strains develop resistance to an antibiotic within 15 to 20 years. Drug resistant strains will only be fought with new antibiotics or synergistic agents.Section: 31-7

41) What antibiotic was approved by the FDA in April 2000, to what family of organic compounds does it belong, and why was its approval particularly important?Answer: Zyvox, a member of the oxazolidinone family of compounds, was approved by the FDA in April 2000. Its approval was important because it was found to cure 75% of patients whose bacterial infections were resistant to all other antibiotics.Section: 31-7


penicillin G; antibioticSection: 31-7

43) How is the therapeutic index of a drug defined?Answer: The therapeutic index of a drug is the ratio of the lethal dose to the therapeutic dose.Section: 31-8

44) Given a choice between two drugs of comparable effectiveness, would you choose the drug with the higher or lower therapeutic index? Explain.Answer: Choose the drug with the higher therapeutic index. The higher the therapeutic index, the greater the margin of safety associated with the drug's use.Section: 31-8

45) In the context of drug design and synthesis, what is a suicide substrate?Answer: A suicide substrate is a drug which binds to the active site of a particular enzyme and subsequently reacts with the enzyme to inactivate it irreversibly.Section: 31-8

46) The technique of relating a property of a series of compounds to biological activity is known as a QSAR. For what does this acronym stand?Answer: quantitative structure-activity relationshipSection: 31-9


47) What name is given to the strategy in pharmaceutical research which employs the concept of mass production, namely that a large group of related compounds can be prepared by covalently linking sets of building blocks?A) combinatorial synthesisB) serendipityC) random screeningD) blind screeningE) molecular modelingAnswer: ASection: 31-11

48) Most antiviral drugs are analogs of ________.A) carbohydratesB) steroidsC) nucleosidesD) proteinsE) vitaminsAnswer: CSection: 31-12


Acyclovir; antiviralSection: 31-12

50) What name is given to drugs which have limited demand and thus prove costly to develop?Answer: orphan drugsSection: 31-13

51) What is a drug?Answer: A compound which interacts with a biological molecule and thereby triggers a physiological effect is called a drug.Section: 98

52) Which of the following common drugs is an antihistamine?A) ClaritinB) NorvascC) ProzacD) TrimoxE) none of the aboveAnswer: ASection: 98


53) Synthroid is used to treat underactivity of the ________.A) kidneysB) hypothalamusC) liverD) pancreasE) thyroidAnswer: ESection: 98

54) Identify the antibiotic(s).A) amoxicillin (Trimox)B) hydrochlorothiazide (Hydrodiuril)C) furosemide (Lasix)D) azithromycin (Zithromax)E) alprazolam (Xanax)Answer: A, DSection: 98

55) Identify the diuretic(s).A) amoxicillin (Trimox)B) hydrochlorothiazide (Hydrodiuril)C) furosemide (Lasix)D) azithromycin (Zithromax)E) alprazolam (Xanax)Answer: B, CSection: 98

56) Identify the anticancer agent(s).A) naproxenB) penicillinC) ibuprofenD) taxolE) 5-fluorouracilAnswer: D, ESection: 98

57) Identify the anti-inflammatory agent(s).A) naproxenB) penicillinC) ibuprofenD) taxolE) 5-fluorouracilAnswer: A, CSection: 98


58) Give the functional groups present in cocaine.A) esterB) alcoholC) tertiary amineD) carboxylic acidE) tertiary amideAnswer: A, CSection: 31-3

59) Give the name of the following structure.

A) lidocaineB) cocaineC) novocaineD) heroinE) benzocaineAnswer: ASection: 31-3

60) Give the molecular modification from morphine to codeine.Answer: addition of a methoxy groupSection: 31-3

61) Give the chemical reaction in which heroin is formed from morphine.A) reductionB) hydrolysisC) oxidationD) methylationE) acetylationAnswer: ESection: 31-3


62) Name the two uses of nitroglycerin.Answer: explosive, dilates blood vesselsSection: 31-5

63) Name the ring structure present in librium, valium, xanax, and rohypnol.Answer: benzodiazepineSection: 31-5

64) Name the following compound.

A) clonazepamB) alprazolamC) chlordiazepoxideD) flunitrazepamE) diazepamAnswer: ESection: 31-5

65) Give the primary use for benadryl.A) diureticB) anti-cancer agentC) antihistamineD) antibioticE) anestheticAnswer: CSection: 31-6

66) Give the structure that sumatriptan is based on.A) acetylcholineB) serotoninC) 4-methylhistamineD) benzodiazepineE) purineAnswer: BSection: 31-6


67) Give the use(s) of prozac.A) antipsychoticB) analgesicC) anti-cancer agentD) antidepressantE) antiinflammatory agentAnswer: A, DSection: 31-6

68) Give the use(s) of thorazine.A) antipsychoticB) antihistamineC) anti-cancer agentD) antidepressantE) lowers body temperatureAnswer: A, B, ESection: 31-6

69) How does penicillinase react with penicillin?Answer: penicillinase destroys penicillin by hydrolyzing its b-lactam ring before the drug can interfere with bacterial wall synthesisSection: 31-7

70) Give the product for the following reaction.

Answer:

Section: 31-7


71) Identify the different sets of building blocks used in combinatorial synthesis.A) benzodiazepinesB) carboxylic acidsC) amino acidsD) estersE) alkylating agentsAnswer: A, C, ESection: 31-11

72) Identify the compound(s) that are nucleosides.A) cytarabineB) ciprofloxacinC) ribavirinD) acyclovirE) idoxuridineAnswer: A, C, ESection: 31-12

73) Identify the compound that is used in treating herpes simplex infections.A) acyclovirB) cytarabineC) ribavirinD) idoxuridineAnswer: ASection: 31-12


Documents

Chapter 31