Final exam 2005

Final exam 2005 - MedicinalChemistry311 Name ‘ JG fl:...

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Unformatted text preview: MedicinalChemistry311 Name ‘ JG fl: December 12, 2005 Final Examination Student No. Use a No. 2 pencil. Write your name on the top of this exam and on the front of the bubble sheet. Use your 8-digit person number (as 10 No.) followed by a blank space t9th]. DO NOT USE YOUR SOC. SEC. NUMBER! Fill in bubble sense where applicable. For the multiple choice questions, select the one best answer. For each question, the correct answer is worth 2 points. Read each question carefully. Double check all your answers! If you change an answer, be certain to erase the original answer completely! 1. Which one of the following drugs does NOT underg metabolic a tivati-flni' B a) cyclophosphamide require MTohoiiL OLTHR‘tbf b~i cytochrome. N50 b) ,ELBBSILQZELB mm W an")an Trimmer- c) acyclovir mum atrium“ d) a; mebwm actub'bf e) 6-mercaptopurilne‘ 2. inhibition of thymidylate synthase by tb§_a_cflyaled_f_Qme_5Lfl_UQLQULaCil results Janhibflion of ALL BUT ONE of the following: D o a) cell division I HN F b) cellular proliferation ‘ )\ l c) DNA synthesis _ 0 N disufiw‘sg H e) synthesiso 'miclylate 5-1:” 3. Which of the following enzymes is responsible for theflmelabolicflcflflflgflhe NW3)? 3 SH '——'---._. a) adenylosuccinate.synthase N b).. hypoxanthine-guanine phosphoribosyl tra_n_sfler_ase (HUPKT) N / i \> c) ‘Gln-PRPP amidotransferase _' R d) thiopurine methyltransferase N t" e) xanthine oxndase 6MP \/ 4. Cyprofloxacin can be taken together with which ONE of the fogowing: O a) aluminum hydroxnde F COOH b) calcium fortified orange juice 0) grapefruitjuice I (1) milk N N e) milk of magnesia N0 A ciptofloxacin F— 5. The mechanism of action of phenobarbital involves f the followin : 9 E 0 CH3 a) complex formation with the GABAA receptor HN b) potentiation of the action of gamma-aminobutyric acid A c) opening the chloride channel 0 o d) binding to an allosteric site of the GABAA receptor H ‘th benzodiazepins for binding e) competition Wt phenobarbital 6. Which of the following statements about phenobarbital is FALSE? a) it is an inhibitor of drug metabolism b) it is a sedative c) it is a CNS depressant d) it is addictive e) it enhances the effects of an inhibitory neurotransmitter 7. The ngabattngamma-vinyl GABA), a drug useful in the treatment of epilepsy. .Jargets which of the following: D ’ a) GABAA receptor (A b) chloride channel 0) glutamate decarboxylase H2NMCOOH H2N COOH d) GABAtransaminase_ GABA vigabatrin e) GABA transporter 8. ALL BUT ONE of the following enzymes require a coenzyme derived from vitamin BB; E- CH20H a) alanine racemase HOCH2 \ OH b) GABAtransaminase I c) dopa decarboxylase N/ CH d) glutamate decarboxyiase 3 e) acetylcholine esterase vitamin BB 9. The larger the value of the germ the narrow indow for the drug. Is this statement TRUE OR FALSE? 5 a) TRUE b) FALSE 10. Which of the following statements about the therapeutic index is correct? C a) TI = maximum effective doselminimum tolerated dose b) Tl = minimum effective doseimaximum tolerated dose C) TI = LD501’ED50 d) T1 = minimum tolerated doseimaximum effective dose e) T1 = minimum tolerated doselminimum effective dose F— 11. Which of the statements below about antibiotic Wis flQT correct? E a) it may be caused by point mutations b) plasmids can carry multiple resistance genes V, c) plasmids may be transferred between different bacterial strains d) it may be acquired by conjugation between bacteria e) it cannot be acquired without mutating the bacterial chromosome 12. ALL BUT ONE othflglJowing may contribute to the emergence and spread of an antibiotic resistant bacterial strain? D a) misuse of antibiotics b) selective killing of the sensitive strain c) selective evolutionary pressure by the antibiotic d) difference in osmotic pressure e) premature termination of treatment a) increased cellular efflux of the drug b) increased cellular uptake of the drug 0) decreased metabolic activation of the drug d) decreased enzymatic degradation of the drug e) decreased affinity of the target to the drug 14. ALL BUT ONE of the following reactions are known to be involvedin _ structure of antibiotics WWW a) oxidation b) hydrolysis c) acetylation d) adenylation e) phosphorylation 1 t 15. Methylation of a single adenine residue in bacterial ribosomal RNA is responsible for resistance to which of the following drugs? 9 a) streptomycin b) cyprofloxacin c) kanamycin d) erythromycin e) tetracycline @ 16. Which of the following is a membrane-derived substrate of cyclooxygenases? A a) arachidonic acid b) oleio acid 0) cholesterol d) inositol e) glycerol 17. Interaction of aspirin wiEncyclgoxyggnasglcpm results in ALLBUT GALE a! the following: ‘ D a O “‘____ '_" li a) conversion of aspirin to salicylic acid OCCH3 b) inhibition of thromboxane A2 synthesis 0) covalent modification of an active site serine residue , OH d) hydrolysis of the acetylated enzyme r . e) inhibition of platelet aggregation asplrln I a '\{ 18. Separation of the chromosomes occurs in which phase of the _ a) G0 b) 61 o) Gil d) S e) M 19. Which of the following is the correct structure of the drug a ril? Clue: the structure of the drug is derived from that of the dipeptide -Ala-L-Pro substituting CH2$H group for the alpha-NHz group of L-Ala. Suggestionf‘draw the structure of L- Ala-L-Pro (all L-amino acids have the S absolute configuration) and find the ' corresponding structure below. B CH3 Q CH3 Q HS 9H3 D HS i N Hs\/KWN -. COOH b 0d e 20. Which group of captopril is responsible for the tight binding of the drug to the zinc at the active site of its target,angio.tensin.converting enzyme (A-(ZE); a) —COO‘ b) -C=O c) —N- d) —CH3 e) -SH 21. ALL BUT ONE of the following may result from the action of the ACE inhibitors, enalaprilat and ly_sinopril:: 'iE, a) lowering of blood pressuie deecreased angiotensin II syflthesis c) vasodilation d) "decreased release of aldosterone e) degradation of bradykinin 22. Which one of the following enzymes was used as a model for ACE in the development of captopril? D “"*-—--—‘_‘. a) acetylcholine esterase b) GABAtransaminase c) phospholipase A2 d) carboxypeptidase A e) dopa decarboxylase 23. Carbidopa is used in the treatment of the symptoms a ' rkinson's disease.‘ ALL BUT ONE of the following statements regardingls correct: C _ HO COOH a) lowers peripheral dopamine levels b) lowers the therapeutic dose of quopa CH3 NH—‘NHz c) crosses the BBB H0 d) prevents decarboxylation of L-dopa e) forms Schlff—base with pyridoxal phosphate \/ 24. Synaptictransmission in the euroninvolve@ the following: carbidopa a) uptake of dopamine (DA) into the postsynaptic terminal b) uptake of tyrosine into the presynaptic nerve terminal I c) decarboxylation of L-dopa d) termination of DA action by monoamine oxidase (MAO) e) termination of DA action by catechol-O-methyltransfersae (COMT) 25. Which of the following is NOTinvolved in the dopa decarboxylase reaction? 0 a) formation of a Schiff-base with pyridoxal phosphate b) bye/1W8? HO COOH HO NH2 c) consumption of 02 d) C — C bond cleavage m2 ———* UV e) formation of dopamine HO HO “93 l dopamine (DA) 26. The combination of carbidopa and L-dopa is effective in the treatmenLQL Parkinson's disease, because both can cross the blood-brain barrierlBBB) by carrier mediated transport. TRUE or FALSE? H0 .3 COOH HO COOH a) TRUE UY UKNHH H H C 2 b) FALSE H0 N 2 H0 .3 L_d°pa carbidopa 27. Which of the following antibiotics acts by inhibition of bacterial protein biosynthesis *by binding to the 308 bacterial ribosomal subunit'fi} abstimmbemg b)_e_rythrornycin; "SOS *1 W Si) N. C) isoniaz'Ld‘ ofldoww Wme gm. d)r_rifampin_ mumm RNA fiMS-Q, e) $929131? 3&5 “:5. S+l~LPeri\[Cln \/ 28. When Wis added to a 3:1 mixture of L-alanineand D-alanine, respectively, which of the following willJlappfll? E ‘ a) all D-ala will be converted to L-aia b) all L-ala will be converted to D—ala 0) ~20% of L-ala will be converted to D—ala d) ~25% of L-ala will be converted to D-ala e) ~33% of L-ala will be converted to D-aia 29. ALL BUT ONE of the following is correct about vancomycig, D a) several genes are responsible for resistance against—it— b) it binds to the D-aIa-D-ala terminal segment of the transpeptidase substrate c) it blocks cell wall synthesis in susceptible bacteria ' d) in resistant strains the D-aIa-D—ala in its target is replaced by_D_—ala-L-Iac e) its high affinity to its target depends on a single, critical H—b . / 30. Penicillin G and cephalosporin C act by an identical mechanism. is this - statement TRUE OR FALSE? A ' a) TRUE . \(xmioL’ b) FALSE [Mo P 'J 31. The seiective toxicity of beta-Iactam antibiotics is the consequence of ALL BUT ONE of the following: ‘ a) thein the beta-lactam rin Lip-Wiper r‘i'fifi‘ig Somme-l b) they inhiit the biosynthems of a unique component of bacterial cells 0) their structure resemble D-ala—D-ala not present in mammalian cells (3!) they inhibit a cross-linking reaction—that occurs only in bacteria . e) their transpeptidase target is absent in mammalian cells 32. The antifungal drug nystatin is selectively toxic to fungi, because it targets a component of the fungal membrane that is not present in mammalian membranes. Which is that component? B a) cholesterol b) ergosterol c) phosphatidyl choline d) fatty acids 9) glycerol esters 33. ALL BUT ONE of the following statements is correct about cyclins and cyclin- dependent kinases (CDK): E) a) they are regulatory proteins b) they are localized in the microsomai fraction c) they control the cell cycle via protein phosphoryiation d) they are most active during checkpoints of the cell cycle e) they are involved in DNA damage assessment 34. Which of the following is the primary target of sbjtonarnides? Q —'_'"'--. a) D-aIa—D-ala synthetase //0 b) dihydrofolate synthetase HZN S__NHR c) dihydropteroate synthase \\ d) folic acid reductase 0 e) thymidylate synthase sulfonamides V 35. ALL BUT ONE of the following statements is correct about the action of penicillin? ' " RCONH s CH3 a) it is biosynthesized in microorganisms 1 CH3 b) it is biosynthesized from 2 amino acids L't‘nfln, M“ “ NJ CO H 2 c) it is a substrate for the transpeptidase d) it forms a reversible covalent bond with its target e) it reacts with the WWam ring V 36. The recently approved anti-AIDS drug enfuvirtide inhibits which one of the following events in the life cycle of HIV? ' O penillin a) budding b) integration . r. 0) virus entry mew d) maturation e) replication 3?. The chemical instability of benzylpenicillin is due primarily to which of the following structural components? C F ———I_ O a) the fusion between the 2 rings NH 5 CH3 b) the thiazolidine ring :f c) the B-Iactam ring CH3 d) the side—chain amide O "'IcozH e) the carbofyl group dew W M. benzylpenicillin 38. What are the absolute configtli‘tatrb'ng‘g? chiral centers in the cephalosporin molecule? 9 a ti 8 a) 68,75 R 7% t 5 b) 65,7R . c) 6R,TS O N / R d) mm COOH e) honest the above 39. Iavulanicacilons antibacterial ac fin is in ' a) TRUE b) FALSE t .s‘ -.—---— 40. Sulfamethoxazole and trimethoprim inhibit 2 sequential reactionsirm'ifefcflaigfl biosynthetic pathway more effectively, than either drug alone. If the first reaction _A to B is inhibited 50%, and 2nd reaction B to C 90%. what would be the yield of product _C? The yield of C in the absence of the drugs is assumed to be 100%. A—'—"B'—”C ’80 fit). :46 fl_ The yield of product C is: % a. to a) 2.50/0 b) 5% C) 100/0 d) 15% - 9) 20%) \h__,.- h“) 41. 6-Aminopenicillanic acid “wit obtained by an matic h drolysis of eniciliin, can be converted to semi- ynthe Ic penicillins by reaction W“ h which one of the following reagents? D H2N a) carboxyiic acids 8 b) HCl émvid as” thaw MK 0) NaOH _ O d) acyl chlorides filamfimm COOH e) H2804 “‘1 6-aminopenicillanic acid 42. Which of the following is NOT shared by _peptidoglycan transpeptidase and fi- lactamase, when they interact with penici m? h "Eh—J ’ I a I j a) penncnllin seryesmbstrate b) an active ' serin r ' e_ attacks the beta-lactam cam—91135119 c) a peniciiloyl'erizyme is? Hormedduringeat‘alysis d) the acyl enzyme intermediate h drolyzes e) the B-lactam ring IS split open ' is3'43. Penicillins that bind tightly to B-lactamasetaturays become hydrolyzed faster than those that bind poorly. is this statement TRUE 0R FALSE? B a) TRUE b) FALSE \ r 4}. lnyancomycin resistance a_criticai H-bond cannotfor—m between the dru and its target. due to the replacement of a Dgalan'me with which of the following? a) L-alanine b) L-threonine c) L-iactate d) D-threonine e) D-iactate 45. Acyclovir (acycioguanosine) undergoes metabolic activation to the triphosphate form, which involves initial phosphorylation to the monophosphate by which one of the following enzymes, which is viraily encoded? O a) thymidyiate kinase N b) thymidine kinase H“ l x) c) thymidine phosphorylase H N/li‘N N d) deoxyguanosine kinase 2 LOW e) guanosine kinase acyclovir 0H 46. ALL BUT ONE of the following is a factor in the selective toxicity of acyclovir: C '____"'—1 a) acyclovir incorporated into viral DNA is not removed by repair enzymes b) phosphoryiation of acyclovir is carried out by an enzyme encoded by the herpes virus, but not by cellular enzymes the herpes viral DNA polymerase is more sensitive to inhibition by acyclovir triphosphate than the host cell DNA polymerase . c) conversion of acyclovir monophosphate to the triphosphate can be carried out only by cellular kinases. not by \dLalcnzyH'Ies d) the herpes viral DNA polymerase is more sensitive to inhibition by acyclovir triphosphate than the host cell DNA polymerase e) metabolic activation to the of the drug occurs only in virally infected cells 47. The mechanism of action of acyclovir involves all but one of the following: _ C a) inhibition of viral DNA chain eiengatipn b) DNA chain termination c) inhibition of viral protein synthesis d) inhibition of herpes virus DNA polymerase 6) inhibition of viral DNA synthesis 48. Which of the following structural feature is rimarfl__res o sible for the actig'i_o_fH ggmnxiLatthemciegular level? 0 a) the presence of a hetercgcyclic ring b) the presence of guanine instead of thymine c) the lack of a 2'-OH group d) the lack of a 3'-0H group e) the presence of a primary OH group 49. ALL BUT ONE of the following result from the lack of fidelity NEW: a) accumulation of coding errors b) highrate ofmutations c) rapid emergence of drug resistance d) need for drug combinations in the therapy of AIDS e) destruction of the immune system ~._____; ‘ 50. ALL BUT ONE of the following enzyme activities are encoded by the HIV genome: ® 0 a) aspartate protease b) reverse transcriptase c) thymidine kinase d) integrase mm 51. What is the substrate for the RNAse H activity of HIV reverse transcriptase? & a) single stranded viral DNA b) viral RNA-DNA hybrids _ c) single stranded viral messenger RNA d) DNA copies of the genomic viral RNA e) viral double stranded proviral DNA 52. D-Cycloserine can cause toxic CNS side effects, due to its ability to deplete pyridoxal phosphate. The administration of which one of the following vitamins can prevent the neurological side effects of D-cycloserine? D NH2 a) vitamin A b) vitamin O CH C) vitamin Be I d) vitamin B1; O__N 8) Vitamin K D-cycloserine 53. infection of CD4 positive T4 lymphocytes by the human immunodeficiency virus requires, in addition to CD4 receptors, the presence of co-receptors, likeCCRsfr- Is this statement TRUE OR FALSE? Q A m a) TRUE b) FALSE ~ "'--—._——— 54. Which one of the following drugs is@an HIV reverse transcriptase inhibitor? g a) nevirapine b) iridi” ir 0) ',_T. d) yo 0 e) D4T I /I HN CH3 55. Which of the following statementsabou AZTi FALSE? E | F" ‘ o N a) it is_a prqdrgg ' 5. O b) it is phosphorylated in the 991mm, 5'-triphosphate HO ‘ Wijphosphate serves _a_s_ a s sTrEté‘for HIV RT 3. AH d) its 3‘-QH group—Ts replaced an agido group N3 e) it§_phosphowlated by afiall __‘__ nz_me "L 56. HIV protease inhibitors interfere with which of the following stages of the viral life cycle? a b —-—— a) attachment to the cell b) uncoating c) re Iication f the viral genome d) maturation of viral proteins e) integration of the provirai DNA 57. The mechanism of action of the AZT, in its active triphosphate form, involves ALL BUT ONE of the following: 0 a) viral DNA chain termination b) inhibition of viral DNA chain elongation c) inhibition of the integLationof proviral DNA d) substrate activity for HIV reverse transcriptase e) inhibition of HIV reverse transcriptase 58. What kind of enzyme inhibitor is :indinavir, which targetsWe. an aspartate protease? Q a) affinity label b) product analog c) transition state analog d) suicide substrate e) irreversible inactivator + indinavir 59. The antiherpes drug 5—iodo-2'-deoxyuridine (IDU) is incorporated into herpes viral DNA by the viral DNA polymerase to cause ALL BUT ONE of the following: A a) chain termination of the flaw b) miss—coding the viral DNA c) mutations d) synthesis faulty viral mRNA e) synthesis of faulty viral proteins 60. 5-lodo-2’-deoxyuridine is isosteric with which one of the following nucleosides? D O F... a) 2’-deoxyadenosine HNJj,I b) 2’—deoxycytidine A | c) 2'-deoxyguanosine 0 N d) 2'—deoxythymidin_e ,6 e) 2'-deoxyinosine- HO .Du tin) imiiol'i N“ OH 61. The development of selective antiviral drugs is difficult than that of antibacteiziab. drugs, because pathogenic viruses are intracellular parasites. Is this statement TRUE OR FALSE? A a) TRUE b) FALSE 62. Which of the following statements about aspirin is FALSE? Aspirin E OCOCH a) serves as a substrate for hepatic hydrolase (I 3 b) can causes gastric irritation c) is an irreversible inhibitor of COX d) inhibits the utilization of arachidonic acid aspirin e) it cannot get absorbed into the lining of the stomach m 63. About half of all cancers have a missing or defective Q53 gene, which is involved in the cellular response to DNA damage. if DNA is cannot be repaired, which process is initiated in a normal cell by the function; p53 iprotein? & B COOH a) necrosis b) apoptosis 0) mitosis d) DNA replication e) DNA repair «64. Which one of the following anticancer drugs act specifically duriflgiiEJfiLhfie of the cell cycle? a) 5—fluorouracil b) 6—mercaptopurine c) taxol d) methotrexate e) cyciophosphamide 65. 5-Fluorouracil (5-FU) is the drug of choice in the treatment of most gastro- intestinal malignancies. In the ceil, it is converted to its active form, 5-fluoro-2’- deoxyuridine 5'-phosphate (FdUMP), which is a mechanism-based inactivator of which enzyme? 0 a) aromatase E- 5 F b) thymidine kinase HN c) thymidine phosphorylase A I d) DNA polymerase 0 2 6 e) thymidylate synthase 5::U <$366. Which one of the following statements is NOT correct about methotrexate (lfiTX), _ _ a drug useful in the therapy of cancer, psoriasis and rheumatoid arthritis? 8 _ '" '————._. a) it requires _a_ctive transport for cellularu ke 0 COOH b) it inhibits—folio acid giogygthesis c) i In Ibitsreductiono dihydrofoiate NH2 [UlfiMCOOH N d) FILEDJJLLS synt esis N e) lug an am ‘\ ‘j/\ / / N N N I l NHZA CH3 methotrexate 67. Regarding the interaction of allopurinol with its target xanthine 959% which of the following statements is FALSE? Allopurinol (J a) binds to the reduced Mo(V|) form of the enzyme b) serves as a substrate for the en_zyr_ne "’ c) competes with Wfor bind_i_gg_t_o_the__enzyme d) is converted to an Isostere o xanthine by the enzyme e) decreases formation of uric acid by the enzyme allopurinol $8. The biosynthesis of estradiol from testosterone, carried out by the enzyme aromatase (CYP450mm). an important target of breast cancer drugs, requires oxidative removal of the 19-CH3-group, which involves L BUT ONE of the following 0 transformations: CH3 CH3 .J. E 0H 0“ a) aromatization of the A-ring 19 CH3 b) conversion of CHO YEWQOOH ——)n- 0) conversion of CH3 to—CHQQH d) conversion of CHOtoGFED'H . e) conversion of_CHzOH to CHO testosterone Ho estradiol 69. Which of the following drugs useful in the treatment of hormone-dependent breast cancer is a competitive inhibitor of aromatase? a) anastrazole b) finasteride c) raloxifen d) tamoxifen e) taxol 70. Which of the following drugs useful in the treatment of hormone-dependent breast . cancer is an antagonist at the estrogen receptor? D P 5 ‘ lo . a) anastrazole b) aminoglutethimide c) finasteride d) tamoxifen e) taxol /"'_""“--_ 71. 19-Nor-19-propenyltestosterone targetswich of the folloWing statements is FALSE regarding this dru ? E a) it serves as a suicide substLatei‘cJ—raromatase b) it alkylates the active siteoiaromatase C) themmbitigrflfigenzyme is irrgversible d) the propenyl group is oxidized by the enzyme e) the carbonyl oxygen of the-drug is rTafduced to OH 0 19-nor-19-propenyl testosterone 72. Which of the following drugs is a topoisomerase II inhibitor? ® 9 a) oamptothecin (Topotecan) b) ethepesideLVP-m) c) adriamycin d) cis-platin e) mechlorethamine 73. Which one of the following vitamins, rich in green vegetables, is known to interfere with the therapeutic effectiveness of the anticoagulant warfarin (Coumadin)? # a) A J: b) B c) D d) E e) K 74. Regarding dopamine, which of the following statements is@correot? C ——_._ a) It is a derivative of tyrosine H0 NHz b) Its reuptake is inhibited by cocaine U/ c) It is degraded by a transaminase 09W? {0’19- H0 d) it is antagonized by chlorpromazine at the DA receptor e) It is a product of dopa-decarboxylase dopamine 75. Which of the following is the ingredient in certain food substances that is primarily responsible for the “cheese-effect” afflicting patients under MAOI medication? E. a) tryptophan b) tryptamine NHz c) thyroxine d) tyrosine H0 e) tyramine 76. ALL BUTONE of the following drugs are incompatible with penicillin: \ E) ‘“-—-___——__ a) captopril b) erythromycin c) gentamycin d) kanamyoin e) streptomycin 77. The beta-lactamase inhibitor clavulanic acid can be classified as: A i K a) suicide substrate b) affinity label 0) transition state analog cl) reversible competitive inhibitor e) reversible non-competitive inhibitor 78. The utility of activated charcoal in emergency treatment of accidental overdose or poisoning cases is primarily due to which of the following: A a) large surface area b) low density 0) amorphous nature d) insolubiiity in water e) lack of elements other than carbon 79. ALL BUT ONE of the following pharmacological activities are attributed to aspirin: D t- t- 9 a) an Ipyre Ic OCCH3 b) anticoagulant c) antiinflammatory d) anticonvulsant OH e) analgesic aspirin 80. Which characteristic activity of aspirin listed in the previous question is not shared by the other NSAIDs? a) b) C) d) 9) IGWEMW1 Ld %. Zb fl. 1c 3. ka 3. 53 m. &e M. to, fl. ab 3. &d M. mb w. Me n. ma 3. flc %. Md w. wd m. wb M. flb n. ma fl. Md M. NC %. fie m. no N. nb m. Ea w. %e m. 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This note was uploaded on 12/16/2009 for the course MCH 311 taught by Professor Kalman during the Spring '08 term at SUNY Buffalo.

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Final exam 2005 - MedicinalChemistry311 Name ‘ JG fl:...

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