Pharmaceutical Chemistry Practice Set

1. Which of the following statement is NOT true with respect to the effect on pharmacodynamics of some chiral drugs?
A. S-Timolol is more potent blocker than R-Timolol
B. D-propranolol is blocker while L- form is inactive
C. S-ibuprofen is active form while R- Ibuprofen is inactive form
D. L-Sotalol is blocker while D-Sotalol is not.

2. Which of the following is an example for the slow and prolonged release (sustained drug action) where the drug has a half life of 6-8 hours and the prodrug has duration of activity about a month?
A. Betamethasone disodium phosphate
B. Phenylbutazone
C. Fluphenazine deconate
D. Chloramphenicol palmitate

3. Aryl allyl ethers undergo [3,3]-sigmatropic rearrangement on heating to allyl phenols is known as
A. Claisen rearrangement
B. Hoffman rearrangement
C. Favroskii rearrangement
D. Bayer-Villiger reaction

4. Which of the following statement is not correct with respect to the effect on pharmacokinetics of some stereo active drugs?
A. L-Methotrexate is better absorbed than D-methpotrexate
B. Racemic omeprazole is more bioavailable than Esomeprazole
C. S-Warfarin has lower volume of distribution(Vd ) than R-warfarin
D. Levocetrizine has smaller Vd than its dextroisomer

5. Reserpine solutions on keeping for long time under day light loses its green colour due to formation of ____
A. 3-Dehydroreserpine
B. 3-Isoreserpine
C. Reserpic acid
D. 3-Deserpidine

6. In which of the rearrangement reactions, an alkyl group migrates with its bonding pair, to an electron deficient carbon atom?
A. Dakin Reaction
B. Hoffman rearrangement
C. Wagner Meerwein rearrangement
D. Bayer-Villiger reaction

7. In the corticosteroids, the substituent that significantly decreases mineralocorticoid activity is _
A. 9-alpha-chloro
B. 21-hydroxy
C. 2-alpha-methyl
D. 16-alpha-hydroxy

8. 2-Chloro-10H-phenothiazine when reacted with 1-(3-chloro propyl)-4-methyl piperazine in presence of Sodamide yields
A. Prochlorperazine
B. Chlorpromazine
C. Quinacrine
D. Promazine

9. Synthesis of which the following compounds involve 2-bromo-1-(2,4-dichlorophenyl) ethanone and propane-1,2,3-triol as the starting materials?
A. Metronidazole
B. Ketoconazole
C. Celecoxib
D. Metamizole

10. 2-Bromo-1-(2,4-dichlorophenyl) ethanone upon reaction with 1H-Imidazole and reduction with NaBH4 followed by treatment with 2,4-dichloro-1-(bromomethyl)benzene yields
A. Metronidazole
B. Ketoconazole
C. Miconazole
D. Chloropromazine

11. Which of the following antihistaminic agents is used for its antiemetic action in the prevention of nausea and vomiting in pregnancy?
A. Diphenhydramine
B. Doxylamine
C. Chlorpheniramine
D. Fexofenadine

12. Which of the following statement is true with respect to the effect on pharmacokinetics of some stereo active drugs?
A. D-Methotrexate is better absorbed than L-methpotrexate
B. Esomeprazole is more bioavailable than Racemic omeprazole
C. R-Warfarin has lower volume of distribution(Vd) than S-warfarin
D. Levocetrizine has greater Volume of distribution( Vd) than its dextroisomer

13. Which among the following is the most active pressor amine among ephedrine isomers?
A. L (-) Ephedrine
B. L (+) Ephedrine
C. D (+) Ephedrine
D. D (-) Ephedrine

14. As per USP Columns listed, L 10 refers to_.
A. Dihydroxypropane groups chemically bonded to porous silica particles: 3 to 10 µm in diameter
B. A rigid spherical styrene divinyl benzene copolymer: 5 to 10 µm in diameter
C. Nitrile groups (CN) chemically bonded to porous silica particles: 3 to 10 µm in diameter
D. Porous silica particles: 1.5 to 10 µm in diameter

15. Condensation of an ester of dialkylglycollic acid with urea in the presence of sodium ethylate followed by N-alkylation with alkyl sulphates gives rise to____
A. 3,5,5-trialkyloxazolidine-2,4,-dione
B. 3,5,5-trialkylpyrazol-1,4-dione
C. 3,5,5-trialkylisoxazolidine-1,4-dione
D. 3,5,5-trialkylpyrazolin-1,4-dione

16. Which of the following NSAID’s is an example for the drug that has rapid competitive binding of COX-1 and COX-2?
A. Ibuprofen
B. Diclofenac
C. Aspirin
D. Indomethacin

17. Which among the following statements is NOT true with regard to hydromorphone?
A. Hydromorphone is 7,8-dihydromorphone
B. The structural unit provides flexibility to permit efficacious hydrogen bond between 6-ketone and mu (µ)receptor
C. Presence of OH group at 14β-i increases analgesic action at least 12 folds with respect to morphine
D. Hydromorphone risks are comparable to that of morphine and includes respiratory depression and constipation

18. The thiazolium ring of aneurine breaks down on reaction with_
A. Alkaline potassium ferricyanide
B. Sodium hydroxide
C. Hydrochloric acid
D. Nitric acid

19. A hexose deoxy sugar cladinose present in Erythromycin-A, has a molecular mass of ___
A. 161
B. 172
C. 176
D. 191

20. Which of the following rearrangement provides an effective method for the synthesis of primary aliphatic and aromatic amines from primary amides?
A. Pinacol rearrangement
B. Hoffmann rearrangement
C. Wagner –Meerwein rearrangement
D. Dakin reaction

21. Ethers undergoing [1,2]sigmatropic rearrangement in the presence of strong base such as amide ion or phenyl lithium to give more stable oxyanion is known as
A. Pinacol rearrangement
B. Hoffmann rearrangement
C. Wagner –Meerwein rearrangement
D. Wittig rearrangement

22. Which among the following structural modifications in morphine produces a derivative that has increased activity as an analgesic compound (compared to morphine)?
A. Methylation of the phenolic -OH group
B. Methylation of the alcoholic -OH group
C. Dealkylation of tertiary nitrogen
D. Oxidation of alcoholic -OH to keto group

23. Which among the following statements is incorrect with regard to properties of pure tocopherols?
A. They are oxidized readily by ferric salts, mild oxidizing agents and by air in presence of alkali.
B. They are activated rapidly by exposure to ultraviolet light.
C. Their antioxidant property for fixed oils is found in the following decreasing order of effectiveness -δ-,γ-,β-,α-i
D. They are destroyed by the accumulating fat peroxides that are decomposed by them.

24. Which among the following is considered as a morphinan analogue of morphine?
A. Codeine
B. Levorphanol
C. Heroin
D. Pentazocine

25. The lone methylene unit in 4-methyl-2-pentanone shows a peak in the 13CNMR spectrum at δ ____ ppm.
A. 22.8
B. 25.0
C. 38.4
D. 53.0

26. Which of the following is an example for the prodrug to enhance the solubility?
A. Betamethasone disodium phosphate
B. Phenylbutazone
C. Fluphenazine deconate
D. Chloramphenicol palmitate

27. Discovered first as an anticancer agent and later found to possess broad spectrum activity against DNA viruses with chemical name of 9-b-D-arabinofuranosyladenine is___
A. Ribavirine
B. Inosiplex
C. Vidarabine
D. Idoxuridine

28. Which of the following anticancer drug obtained from plant source is a topoisomearse inhibitor and acts on G2 Phase?
A. Paclitaxel
B. Etoposide
C. Vinblastine
D. Vinorelbine

29. This pyrimidinone analogue, binds with integrase, a viral enzyme essential to the replication of both HIV-1 and HIV-2. By doing so, it inhibits strand transfer, the third and final step of provirus integration, thus interfering with the integration of reverse-transcribed HIV DNA into the chromosomes of host cells.
A. Zidovudine
B. Delavirdine
C. Ritonavir
D. Raltegravir

30. To prevent rapid degradation of N-formimidoyl derivative of thienamycin by renal dipeptidase enzyme, co-administration of this enzyme inhibitor drug _________ is recommended?
A. Imipenem
B. Cilastatin
C. Cefipime
D. Betamipron

31. Which of the following organic reactive intermediate is involved in Wolff rearrangement?
A. Nitrene
B. Carbene
C. Carbocation
D. Carbanion

32. This thymidine analogue, a NRTI gets phosphorylated in the host cells to triphosphate and selectively inhibits viral reverse transcriptase.
A. Zidovudine
B. Delavirdine
C. Ritonavir
D. Raltegravir

33. In which of the following conditions H2 receptor blockers cannot be used effectively?
A. Peptic Ulcer
B. GERD (Gastro Esophagul Reflux Disease)
C. Zollinger Ellison syndrome
D. Insomnia and anxiety for sedation

34. Which among the following statements is not true with regard to the properties of Ascorbic acid?
A. Acidic character is due to the two enolic hydroxyls, the C-3 hydroxyl that has pKa of 4.9 and the C-2 hydroxyl that has pKa of 9.2
B. Ascorbic acid cannot be synthesized in primates due to lack of the liver microsomal enzyme L-gulonolactone oxidase
C. Aqueous solution of ascorbic acid is not very stable and can undergo oxidation under aerobic conditions.
D. Ascorbic acid is chemically [1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one

35. Which among the following is not a component of ergotoxine?
A. Ergocristine
B. Ergocryptine
C. Ergocine
D. Ergocornine

36. Which among the following is a prodrug for ampicillin?
A. Benzathine penicillin
B. Pivampicillin
C. Ticarcillin
D. Piperacillin

37. H NMR low resolution spectrum of Ethyl-N-methyl carbamate shows _____ signals; whereas in high resolution the N-CH absorption at δ ______ ppm is split in to ________.
A. four, 2.78, doublet
B. three, 3.64, doublet
C. four, 2.82, triplet
D. three, 3.33, triplet

38. If a molecule has two chloro- substituents and one bromo- substituent, the isotopic cluster peaks expected in the mass spectrum of such molecule has a ratio of ___
A. 3:7:5:1
B. 18:12:2
C. 9:15:7:1
D. 9:6:1:1:1

39. Which of the following intermediate can be trapped by Diels-Alder reaction while determining a reaction mechanism?
A. Nitrene
B. Benzyne
C. Dichorocarbene
D. Triphenyl methyl

40. Dexamethasone has the following functions at the positions of 20 -____________, 11-___________, 17-_______________and at 21-___________________.
A. oxo; beta-hydroxy; alpha-hydroxy; hydroxy
B. oxo; alpha-hydroxy; alpha-hydroxy; alpha-hydroxy
C. alpha-hydroxy; beta-hydroxy; alpha-hydroxy; beta-hydroxy
D. beta-hydroxy; alpha-hydroxy; alpha-hydroxy; hydroxy

41. The compound 3-Dehydroretinol is __
A. Vitamin A
B. Vitamin A1
C. Vitamin A2
D. Vitamin A3

42. Macrolides are basic in nature due to this specific substituent —-
A. Dimethyl amino group on the lactone ring
B. Dimethyl amino group on the sugar unit
C. Hydroxyl group on the lactone ring
D. Hydroxyl group on the sugar unit

43. Which of the following is NOT considered as a carbocations?
A. Adamantly
B. 1-trishomobarrelyl
C. Triphenyl methyl
D. Dichlorocarbene

44. 2,2,2-Trifluoro -1-imidazol-1-yl ethanaone and acetophenone are used as starting materials for the synthesis of …………
A. Metronidazole
B. Ketoconazole
C. Miconazole
D. Celecoxib

45. In the spectral region from 3300 to 3100 cm , the N-H stretching mode of the -CO-NH- group in peptides appears as _____ band/s due to _______?
A. one; N-H stretching vibration
B. one; C-N stretching vibration
C. two: N-H stretching vibration and its coupling with overtone of N-H deformation mode
D. two: N-H stretching vibration and its coupling with overtone of C-N stretching mode

46. Which of the following antihistaminic agents is a non sedating H1 receptor antagonist?
A. Cetrizine
B. Loratadine
C. Chlorpheniramine
D. Doxylamine

47. Identify this organic reactive intermediate, in which the central atom is electron – deficient, has a sextet of electrons and sp2 hybridized & planar in shape.
A. Nitrene
B. Carbene
C. Carbocation
D. Carbanion

48. Which of the following conditions is NOT true as per Saytzeff‘s rule?
A. Doesn’t apply when the base is bulky
B. Doesn’t apply when the leaving group is poor
C. May not apply when conjugated dienes might be formed
D. Applies only when less substituted alkenes are formed

49. Which of the following NSAID’s has the ability for rapid reversible binding followed by covalent modification of COX-1 and COX-2?
A. Ibuprofen
B. Diclofenac
C. Aspirin
D. Indomethacin