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Nomenclature Exam August 18, 2008 Dr. Adams PHAR 412 Principles o P!arm " #ed $!em NAME_______KEY_____________________

Make sure you write your name on the top of the first page and on your answer sheet. Choose the single %est answer unless otherwise indicated. n the answer sheet pro!ided" please clearly mark your answers with a dark pencil. Erase errors completely. Each #uestion is worth one $%& point. 'here are () #uestions. &E '(RE )* +N$,(DE -*(R P+N " )E') .ER'+*N *N )HE AN'/ER 'HEE)0 *rug names marked with an asterisk $+& are 'op ,-- drugs. %. The

endogenous mineralocorticoid aldosterone contains:

O HO CH3 H O H H CHO OH

A. .. C. *. E.

A single ketone functional group. 'wo ketone functional groups. 'hree ketone functional groups. A car/o0ylic acid. .oth C 1 *. HCl (Atarax)* is a first generation antihistamine that contains:

(. Hydroxyzine

N CH2CH2
2ydro0y3ine $Atarax&+

CH2CH2OH

Cl

A. .. + C. *. E.
,. The

A secondary $( & amine" a primary $% & alcohol" and an ether. o o A tertiary $, & amine" a secondary $( & alcohol" and an ether. o o A tertiary $, & amine" a primary $% & alcohol" and an ether. o o A secondary $( & amine" a secondary $( & alcohol" and an ester. o o A tertiary $, & amine" a primary $% & alcohol" and an ester.
O OH

proper name of the following molecule is:

A. .. C. *. E.

.en3oic Acid Cycloheptane Car/o0ylic Acid 2e0anoic Acid Cyclohe0ane Car/o0ylic Acid 2eptanoic Acid

4. The

following substituent is called:

CH2

A. .. C. *. + E.
6. Buspirone

5henol 5henyl .en3aldehyde Cyclohe0yl .en3yl (Buspar)* a serotonin receptor agonist used as an anxiolytic contains a
O N N (CH2)4 N
.uspirone $Buspar&

(an):
N N

A. .. C. *. + E.

Amide 7uaternary amine Car/amate 8rea 9mide

). !eostigmine

(Prostigmin) is an acetylcholinesterase inhibitor used to treat myasthenia gra"is that contains a(an):
O O
Neostigmine

N(CH3)2

N(CH3)3 Br

A. + .. C. *. E.
:. The

Car/amate and a tertiary $, & amine. o Car/amate and a #uarternary $4 & amine. o Car/onate and a tertiary $, & amine. o Car/onate and a #uarternary $4 & amine. Ester and a car/onate.
O HO CCH2CHCH2CH3 CH2CH3

correct #$%&C name for the following compound is:

A. .. + C. *. E.

,;methyl;he0anoic acid (;ethyl;/utanoic acid ,;ethyl;pentanoic acid ,;heptanoic acid (;ethyl;pentanoic acid

<. Chlorpromazine

(Thorazine) is a phenothiazine compound with "arious uses' #t may be metabolized in the body to the structure shown on the right below that is called a (an):
S N Cl N Cl CH2CH2CH2N(CH3)2 O S

$!lorproma1ine CH2CH2CH2N(CH3)2 2Thorazine3

A. .. + C. *. E.
>. The

Amine Car/o0ylic Acid =ulfo0ide =ulfone =ulfhydryl

H3C H N HN N S N CN CH3 NH

H( receptor antagonist cimetidine (Tagamet) contains a (an):

A. .. C. *. + E.
%-. Based

?itro @roup Amide 9mide =ulfo0ide 'hioether

on the #$%&C system what is the substituent in the ) position on the molecule below*
H3CO CH3CH2CH2 CH3CH2CH2CH Br CHCH2CH3 CH2CH3

A. .. + C. *. E.
%%. $sing +

Ethyl 5ropyl .romo Metho0y ctene the al+ene abo"e what is the name of the parent chain* ctene ?onene 2eptene 2e0ene .utene

A. .. C. *. E.

%(. ,smolol

(Brevibloc) is a short acting beta-bloc+er that contains:

CH3 O OH NH CH3

O O CH3

Esmolol Brevibloc
o

A. + .. C. *. E.

A primary $% & alcohol and a secondary $( & amine. o o A secondary $( & alcohol and a secondary $( & amine. o o A secondary $( & alcohol and a primary $% & amine. o o A primary $% & alcohol and a primary $% & amine. o o A secondary $( & alcohol and a tertiary $, & amine. (Biaxin)* is an antibiotic that contains:
CH3 O HO HO H3C H3CH2C H3 C H3CO CH3 OCH3 CH3 OH CH3 HO O (H3C)2N O

%,. Clarithromycin

CH3

O O CH3

$larit!rom4cin Biaxin O

O H3 C

A. + .. C. *. E.
%4. The

Amide Ester Car/onate Car/amate Aldehyde configuration of this geometric isomer is:
CH3CH2CH2 CH2CH2CH3

ClCH2CH2

CH3

A. .. C. + *. E.

'rans or A 'rans or E Cis or A Cis or E d"l

%6. &

possible route of metabolism for felbamate (Felbatol) is shown below' .hat is the new functional group*
O O
Bel/amate Felbatol

O NH2 NH2 H O C O NH2

C C O

A. .. C. *. E.

An Aldehyde A Car/o0ylic Acid A 2ydro0yl A Car/onate An Aromatic 2ydro0yl

%). Haloperidol

decanoate (Haldol) an anti-psychotic gi"en as an #/ depot contains all of the following EXCEPT:
O O F O Cl N C(CH2)8CH3

A. Ester .. Ketone C. Amine + *. Car/onate E. 2alogen %:. Ciprofloxacin (Cipro)* is a fluoro0uinolone antibiotic that contains all of the following EXCEPT:
O F COOH

N HN
Ciproflo0acin Cipro

A. A secondary $( & amine. o .. A tertiary $, & amine. C. A ketone. *. A car/o0ylic acid. + E. An imide. %<. Captopril (Capoten)* is an &C, #nhibitor that contains:

O HS CH2 CH C
Captopril $Capoten&

N COOH

CH3

A. .. + C. *. E.
%>. 1efering

A thioether and a tertiary $, &amine. o A tertiary $, &amine and a car/o0ylic acid. A car/o0ylic acid and an amide. A thioether and a car/o0ylic acid. A thioether and an amide.

to the structure of captopril what is the relationship of the thiol group (2H) to the carbonyl* A. alpha + .. /eta C. gamma *. C E. =
(-. Torsemide

(Demadex)* is a diuretic' .hat is the relationship between the amine connecting the aromatic rings and the methyl group*
CH3 CH3 CH CH3 NH NH
'orsemide $Demadex&

NH

SO2

N
+

A. .. C. *. E.

o $ortho& m $meta& p $para& alpha /eta (an analgesic 3 cough suppressant respecti"ely) & hydroxyl &n amine & methoxy ether

(%. Both

/orphine* 3 Codeine* contain: #' ##' ###'

CH3 N H N

CH3

HO

Morphine

OH

H3CO

Codeine

OH

A. .. C. *. E.

nly 9 1 99 are true. nly 9 1 999 are true. nly 99 1 999 are true. All of the a/o!e $ 9" 99" 1 999& are true. ?one of the a/o!e are true.

((. !ystatin

(Mycostatin) an antifungal contains a (an): #' ,ster ##' ,ther ###' &mine
OH OH H3C O OH

HO

O CH3

OH

OH

OH

OH

O COOH

H3C O O OH OH NH2 CH3

N4statin

A. .. C. + *. E.
(,. The

nly 9 1 99 are true. nly 9 1 999 are true. nly 99 1 999 are true. All of the a/o!e $9" 99" 1 999& are true. ?one of the a/o!e are true.

mono-amine oxidase-B (/&4-B) inhibitor selegiline (Eldepryl) is a chiral molecule' The generic name is often written: (-)1-selegiline' The (1) indicates: A. 'he direction of the rotation of plane;polari3ed light. + .. 'he a/solute configuration of the chiral center /ased on the Cahn;9ngold;5relog con!ention. C. 'he configuration /ased on glyceraldehyde as a reference. *. 'he a/solute configuration /ased on the direction of the rotation of plane;polari3ed light. E. 'he fact that this drug has serious negati!e effects and should only /e used as a last resort.
(4. 2ulbactam

a penicillinase inhibitor contains a (an):

H O S N O O CH3 CH3

=ul/actam COOH

A. .. C. *. + E.

=ulfonamide 'hioether =ulfhydryl =ulfo0ide =ulfone

(6. 2ulfamethoxazole

is an antibiotic used in compbination with trimethoprim as Bactrim*' 2ulfamethoxazole contains a(an):

O NH2 S NH O
'ul amet!oxa1ole

N O CH3

A. .. C. + *. E.
(). The

=ulfone =ulfo0ide 'hioether =ulfonamide Ester

group below is the pharmacophore for a class of antidiabetic agents including glipizide ( lucotrol)*' The circled group is called:
O R1 S O N H O N H R2

A. .. C. *. + E.

Car/amate Amine 9mide Amide 8rea