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Patrick: An Introduction to Medicinal Chemistry 3e

Chapter 16: Antibacterial Agents

Type: multiple choice questionTitle:Chapter 16 Question 0101) What structure do the sulonamides mimic !hen actin" as en#yme inhi$itors%Feedback:Para&Amino$en#oic acid is a su$strate or the en#yme dihydropteroate synthetase' (he

sulonamides mimic this eature'ihydropteroate is the product rom this en#yme catalysed reaction' *&"lutamic acid is added todihydropteroate to orm dihydroolate' +either are mimicked $y the sulonamides' (he sulonamides arederi,ati,es opara&aminosulonic acid and so this is not mimicked either'Page reference:3-.a' ihydropteroate$' *&"lutamic acidc' Para&aminosulonic acid/d' Para&amino$en#oic acid

Type: multiple choice questionTitle:Chapter 16 Question 00) Which o the ollo!in" is the "eneral mechanism o action or sulonamides%Feedback:(he sulonamides inhi$it dihydropteroate synthetase' uch inhi$ition pre,ents the synthesiso pyrimidine nucleic acid $ases !hich in turn pre,ents the synthesis o nucleic acids'Page reference:3-/a' Inhi$ition o an en#yme re2uired or the synthesis o important nucleic acid $uildin" $locks'$' Inhi$ition o cell !all synthesis'c' isruption o protein synthesis'd' Inhi$ition o nucleic acid transcription and replication'

Type: multiple choice questionTitle:Chapter 16 Question 0303) Which o the ollo!in" is the "eneral mechanism o action or &lactams%Feedback:(he &lactams inhi$it an en#yme called transpeptidase !hich is responsi$le or the last stepo cell !all synthesis'Page reference:3-a' Inhi$ition o a meta$olic en#yme'/$' Inhi$ition o cell !all synthesis'c' isruption o protein synthesis'd' Inhi$ition o nucleic acid transcription and replication'

Type: multiple choice questionTitle:Chapter 16 Question 0404) Which o the ollo!in" is the "eneral mechanism o action or ,ancomycin%Feedback:5ancomycin $inds to the $uildin" $locks re2uired or cell !all synthesis and pre,ents them$ein" incorporated into the "ro!in" cell !all'Page reference:3-a' Inhi$ition o a meta$olic en#yme'/$' Inhi$ition o cell !all synthesis'c' isruption o protein synthesis'd' Inhi$ition o nucleic acid transcription and replication'

Type: multiple choice questionTitle:Chapter 16 Question 0.0.) Which o the ollo!in" is the "eneral mechanism o action or tetracyclines%Feedback:(he tetracyclines $ind to ri$osomes and inhi$it the translation process that normally leads tothe synthesis o ne! proteins'Page reference:3-a' Inhi$ition o a meta$olic en#yme'$' Inhi$ition o cell !all synthesis'

/c' isruption o protein synthesis'd' Inhi$ition o nucleic acid transcription and replication'

OXFORDH i g h e r E d u c a t i o n 78ord 9ni,ersity Press 006' All ri"hts reser,ed'


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Type: multiple choice questionTitle:Chapter 16 Question 0606) What term is used to descri$e the inhi$ition o t!o dierent en#ymes in the same $iosyntheticpath!ay%Feedback:e2uential $lockin" is more eecti,e than inhi$itin" one or other o the separate en#ymes' Itallo!s lo!er and saer doses o each inhi$itor to achie,e the same eect as usin" one inhi$itor'

;n#yme inhi$ition reers to any dru" that inhi$its an en#yme' Multidru" therapy si"niies that more thanone dru" is used in a therapy $ut does not mean that the dru"s are actin" at t!o dierent en#ymes inthe same $iosynthetic path!ays' Parallel inhi$ition is not a term that is used in medicinal chemistry'Page reference:3-y chemical hydrolysis o $en#yl penicillin !ith sodium hydro8ide

Type: multiple choice question

Title:Chapter 16 Question ==) What is meant $y a semi&synthetic process%Feedback:A semi&synthetic synthesis in,ol,es the use o a natural product and con,ertin" it to thedesired product'Page reference:3=6&3=

c' tructure Cd' tructure

Type: multiple choice questionTitle:Chapter 16 & Question ==) Which o the ollo!in" statements is untrue%Feedback:A $acterial cell is prokaryotic !hereas an animal cell is eukaryotic'Page reference:3-1&3-/a' A $acterial cell is eukaryotic !hereas an animal cell is prokaryotic'$' A $acterial cell has a cell !all !hereas an animal cell does not'c' >acterial cells do not ha,e a !ell deined nucleus !hereas animal cells do'd' >acteria may contain en#ymes that are not present in animal cells'

Type: multiple choice questionTitle:Chapter 16& Question =3



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=3) Which o the ollo!in" dru"s act $y inhi$itin" an en#yme re2uired or the synthesis o important nucleicacid $uildin" $locks%Feedback:(he sulonamides inhi$it dihydropteroate synthetase' uch inhi$ition pre,ents the synthesis opyrimidine nucleic acid $ases !hich in turn pre,ents the synthesis o nucleic acids'Page reference:3-a' K&lactams

$' Fluoro2uinolones/c' ulonamidesd' ;rythromycin

Type: multiple choice questionTitle:Chapter 16& Question =4=4) Which o the ollo!in" dru"s act $y inhi$itin" cell !all synthesis%Feedback:(he K&lactams inhi$it an en#yme called transpeptidase !hich is responsi$le or the last step ocell !all synthesis'Page reference:3-/a' &lactams$' Fluoro2uinolonesc' ulonamides

d' ;rythromycin

Type: multiple choice questionTitle:Chapter 16& Question =.=.) Which o the ollo!in" dru"s inhi$its cell !all synthesis%Feedback:5ancomycin $inds to the $uildin" $locks re2uired or cell !all synthesis and pre,ents them $ein"incorporated into the "ro!in" cell !all'Page reference:3-/a' 5ancomycin$' (etracyclinesc' Cephalosporinsd' Polymy8ins

Type: multiple choice questionTitle:Chapter 16& Question =6=6) Which o the ollo!in" dru"s act $y disruptin" protein synthesis%Feedback:;rythromycin $inds to ri$osomes and inhi$its the translation process leadin" to ne! proteins'Page reference:3-a' &lactams$' Fluoro2uinolonesc' ulonamides/d' ;rythromycin

Type: multiple choice questionTitle:Chapter 16& Question = is penicillin 5 !hich is also kno!n as pheno8ymethylpenicillin' It is similar in structure topenicillin ? $ut has an e8tra o8y"en atom $et!een the aromatic rin" and the rest o the molecule'tructure C is 6&aminopenicillanic acid and structure is a cephalosporin structure called ceale8in'Page reference:3-=

a' tructure A/$' tructure >c' tructure Cd' tructure

Type: multiple choice questionTitle:Chapter 16& Question 10.10.) Which o the ollo!in" statements is true re"ardin" the properties o $en#ylpenicillin%Feedback:Penicillins are $actericidal a"ents and not $acteriostatic a"ents since they acti,ely kill $acterialcells' >en#ylpenicillin has "ood acti,ity a"ainst certain types o $acterial species $ut not all' It is alsosuscepti$le to attack $y $acterial &lactamases !hich makes it ineecti,e a"ainst these $acterial strains' Itis !ron" to say that $en#ylpenicillin has no side eects' Certain indi,iduals can $e aller"ic to$en#ylpenicillin'Page reference:3-=&3=0/a' It is a $actericidal a"ent$' It is acti,e o,er a !ide ran"e o $acterial speciesc' It is resistant to &lactamasesd' It has no side eects

Type: matching questionTitle:Chapter 16 & Question 106106) (he dia"ram sho!s a "eneral structure o penicillins'

Match the ollo!in" unctional "roups or rin"s !ith the re"ions sho!n'

Feedback:All our "roups are important to the acti,ity o penicillinsPage reference:3-=a' Car$o8ylic acid J e"ion $' econday amide J e"ion C

c' (hia#olidine J e"ion >d' &lactam J e"ion A



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Type: multiple choice questionTitle:Chapter 16& Question 10c' tructure Cd' tructure


Title:Chapter 16& Question 1.1.) Which o the ollo!in" structures is cla,ulanic acid%

Feedback:tructures A C and are thienamycin ta#o$actam and sul$actam respecti,ely'Page reference:41a' tructure A/$' tructure >c' tructure Cd' tructure

Type: multiple choice questionTitle:Chapter 16& Question 1616) Which o the ollo!in" structures does not tar"et the transpeptidase en#yme%Feedback:Cla,ulanic acid inhi$its the &lactamase en#yme and pre,ents the en#yme rom deacti,atin"penicillins'Page reference:41&413

a' Penicillin ?/$' Cla,ulanic acidc' Ceale8in



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d' (hienamycin

Type: multiple choice questionTitle:Chapter 16& Question 1/c' tructure Cd' tructure

Type: multiple choice questionTitle:Chapter 16& Question 13

13) What is the name o the preparation containin" ta#o$actam and piperacillin%



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Feedback:(he com$ination o amo8icillin and cla,ulanic acid is sold as Au"mentin' (he com$ination ocla,ulanic acid and ticarcillin is sold as (imentin' (he com$ination o ampicillin and sul$actam is sold as9nasyn' osyn is a com$ination o ta#o$actam and piperacillin'Page reference:414a' (imentin$' 9nasyn

/c' osynd' Au"mentin

Type: multiple choice questionTitle:Chapter 16& Question 133133) What anti$acterial a"ent !orks $y mimickin" &alanine%Feedback:&Cycloserine mimics &alanine and inhi$its *&Ala racemase and &Ala&&Ala li"ase' (he ormeren#yme catalyses the racemisation o *&Ala to &Ala' (he latter en#yme catalyses the linka"e o t!o &Alaamino acids to "i,e the dipeptide &Ala&&Ala'(he other a"ents mentioned inhi$it cell !all synthesis at dierent sta"es'Page reference:414&41.a' 5ancomycin/$' &cycloserine

c' >acitracind' Penicillin ?

Type: multiple choice questionTitle:Chapter 16& Question 134134) What sort o structure is streptomycin%

Feedback:treptomycin is an amino"lycoside so named $ecause it contains car$ohydrate rin"s !ith

amino su$stituents'Page reference:44&4.a' A penicillin$' A tetracyclinec' A macrolide/d' An amino"lycoside

Type: multiple choice questionTitle:Chapter 16& Question 13.13.) What sort o structure is erythromycin%



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Feedback:;rythromycin is a macrolide containin" a lar"e 14 mem$ered rin"s'

Page reference:4a$y yndrome$' Aller"ic reactionsc' *o!erin" o $lood pressured' Anaemia

Type: multiple choice questionTitle:Chapter 16& Question 13-13-) Which unctional "roup is thou"ht to $e chiely responsi$le or the to8icity o chloramphenicol%



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Feedback:Aromatic nitro "roups are normally a,oided i possi$le since they commonly cause to8ic eects'Page reference:46a' A secondary alcohol/$' An aromatic nitro "roupc' An alkyl chlorided' A primary alcohol

Type: multiple choice questionTitle:Chapter 16& Question 13=

13=) Which o the ollo!in" statements is alse re"ardin" erythromycin%Feedback:;rythromycin is one o the saest anti$iotics currently in use'Page reference:4

Type: multiple choice questionTitle:Chapter 16& Question 141141) Which o the ollo!in" structures is a luoro2uinolone%



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Feedback:tructure A is a luoro2uinoline' tructure > is a cephalosporin' tructure C is a tetracycline'

tructure is chloramphenicol'Page reference:4-&431/a' tructure A$' tructure >c' tructure Cd' tructure

Type: multiple choice questionTitle:Chapter 16& Question 1414) Which statement is alse re"ardin" the luoro2uinoline anti$acterial a"ents%Feedback:(he dru"s tar"et en#ymes called topoisomerases' Delicases catalyse an un!indin" process andthe topoisomerases are re2uired to relie,e the strain resultin" rom this uncoilin"'Page reference:4=&431

/a' (hey tar"et en#ymes called helicases$' (hey inhi$it replicationc' (hey inhi$it transcriptiond' (hey sta$ilise an en#yme&+A&dru" comple8 !here our luoro2uinoline molecules are stacked to"ether

Type: multiple choice questionTitle:Chapter 16& Question 143143) Prola,ine is an anti$acterial a"ent that !as used in the second !orld !ar' Which one o the ollo!in"structures is prola,ine%

Feedback:(he other structures are sulphapyridine @A) nalidi8ic acid @C) and chloramphenicol @)'Page reference:431a' tructure A/$' tructure >c' tructure Cd' tructure

Type: multiple choice questionTitle:Chapter 16& Question 144144) Which o the ollo!in" anti$acterial a"ents tar"ets +A%Feedback:Prola,ine acts as an intercalator slippin" $et!een the stacked $ase pairs o +A'Page reference:431



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a' Penicillin 5$' ;rythromycin/c' Prola,ined' &cycloserine


Title:Chapter 16& Question 14.14.) Which o the ollo!in" dru"s acts as an intercalator%Feedback:Prola,ine its $et!een the $ase pairs o the +A dou$le heli8 and disrupts its structure'Page reference:431a' Methacillin$' ulathia#olec' 5alinomycin/d' Prola,ine

Type: multiple choice questionTitle:Chapter 16& Question 146146) Which o the ollo!in" structures has $een used as a topical a"ent or skin inections and as a meanso com$atin" the transmission o S. aureusin hospitals%

Feedback:tructure A is mupirocin' (he other structures are usidic acid riampicin and methenamine'Page reference:43./a' tructure A$' tructure >c' tructure C

d' tructure

Type: multiple choice questionTitle:Chapter 16& Question 14

patrick tb ch16

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