[ORGANIC MEDICINAL CHEMISTRY] PCAOP VIOLET

1. The functional group attached to the acyl amino group is called a/an:

A) Phenoxyethyl

B) Isoxazoyl

C) Imidazole

D) Benzyl

E) Methoxypheny

B Isoxazoyl

2. Halogen substituents are best placed in what position?

A) 1,2-substitution

B) 1,3-substitution

C) 1,4-substitution

D) BothAandB

E) BothAandC

A 1,2-substitution

3. This antibiotic is primarily indicated for what type of infection?

A) Klebsiella

B) Enterobacter

C) Psudomonas

D) Staphylococci

E) Streptococi

D Staphylococci

4. Adding more than 1 chloride atoms in the structure confers what modification on the pharmacokinetic profile of the drug?

A) Liberation

B) Absorption

C) Distribution

D) Metabolism

E) Excretion

C Distribution

5. What is the role of chloride atoms in the structure?

A) Increase the susceptibility to penicillinase

B) Increasing the plasma concentration

C) Acid resistance property

D) Increase in parenteral absorption

E) Increase in oral absorption

B Increasing the plasma concentration

6. Preservatives like parabens increase their preservative property by

A) Reducing the parent compound

B) Decreasing molecular weight

C) Attaching a halogen to the parent compound

D) Substituting the parent compound with a

lipophilic group

E) Increasing the molecular weight

E Increasing the molecular weight

7. Sodium pump is an example of A.)enzyme-linked tyrosine kinase receptor B.) G-protein coupled receptor

C.) Ion- channel

D.)Gene transcription-linked receptor

E.) None of the above

C Ion- channel

8. This is an approach in drug discovery wherein there is already an existing drug that can be used to identify a new lead compound?

A) Random Screening

B) Molecular Docking

C) Parent compound modification

D) Biotechnology techniques

E) Rational Drug Design

A Random Screening

9. Azeotropic distillation of benzene is done in what concentration of ethanol?

A) 95%

B) 70%

C) 50%

D) 99%

E) 10%

D 99%

10. Radical reactions may also proceed using this reagent

A) Bromine water

B) Hydrogen peroxide

C) Nitric acid

D) Sodium oxalate

E) Potassium bitartrate

B Hydrogen peroxide

For

numbers 11-14, refer to the series of the reaction

11. What is the reagent needed for the first reaction?

A) NaOH/ Oxidizing agent

B) CH3 Cl/AlCl3

C) HNO3/H2SO4

D) NaOH/ Reducing agent

E) CH3Br/NaNH2

B CH3 Cl/AlCl3

12. The product formed with the reaction is

A) Benzyl alcohol

B) Phenol

C) Benzoic acid

D) Xylene

E) Anisole

C Benzoic acid

13. The reagent needed for the reaction to proceed is

A) CH3Br/NaNH2

B) NaOH/Reducing agent

C) CH3COCl/AlCl3

D) HNO3/H2SO4

E) NaOH/ Oxidizing agent

D HNO3/H2SO4

14. The reagent needed for the reaction to proceed is

A) NaOH/Oxidizing agent

B) CH3Br/NaNH2/NO2

C) H2O/H2SO4

D) NaOH/Reducing agent

E) NBS

D NaOH/Reducing agent

15. When a carbonyl group reacts with a secondary amine, what will be the resulting product?

A) Imine

B) Amide

C) Tertiary amine

D) Enamine

E) Secondary amine

DEnamine

16. The addition of hydrogen molecule to an alkene is catalyzed by what metal?

A) Silver

B) Palladium

C) Berrylium

D) Gallium

E) Osmium

B Palladium

17. Methoxybenzene is also known as _____

A) Anisole B) Toluene C) Aniline D) Xylene E) Anethole

A Anisole

18. Which of the following compounds can be use to synthesize primary alcohol?

A) Propane

B) Formaldehyde C) 3-chloropentane D) Acetone

E) Ethanamine

A Propane

19. Which of the following cephalosporin is excreted in bile?

A) Cefixime

B) Cefotaxime C) Ceftriaxone D) Moxalactam E) Loracarbef

C Ceftriaxone

21. Preservatives use for molds

A) Ethylparaben

B) Methylparaben C) Butylparaben

D) Propylparaben E) Isopropylparaben

B Methylparaben

22. Which is true about drug absorption?

I. For weakly acidic drug, it must e in its

unionized form

II. For weakly acidic drug, it must be in its

ionized form

III. For weakly basic drug, it must be in its

unionized form

IV. For weakly basic drug, it must be in its

ionized form

A) I, II, III B) I and III

C) II and IV

D) III and IV

E) I and III

E I and III

23. This anti-convulsant compound is susceptible to what metabolic pathway?

A) Aromatic hydroxylation

B) Methylation

C) Sulfate conjugation

D) Oxidative deamination

E) GSH conjugation

A Aromatic hydroxylation

For numbers 24-26, refer to the general structure of penicillin

24. Which of the following will confer resistance against beta lactamases when synthesizing analogs of penicillin?

A) Halogens

B) Ring deactivators

C) Electron withdrawing group

D) Bulky group

E) Ring activators

D Bulky group

25. What functional group is being modified if formulation into a salt is needed?

A) Amide

B) Carboxylic acid

C) Carbonyl

D) Alkyl

E) 225g

C Carbonyl

26. What is the functional group attached to the beta lactam ring?

A) Aryl amide

B) Acyl amide

C) Polyamide

D) Carboxyamide

E) Phenylamide

A Aryl amide

27. Which of the following is true on ideal antiseptic?

I. Low toxicity

II. Sustained and rapid lethal action against

microorganisms

III. High surface tension

IV. Non-irritating and non-allergenic

A) I, II, IV

B) III only

C) I, II, III, IV D) II and III E) III and IV

A I,II, IV

28. Aztreonam can elevate this enzyme

A) Creatinine kinase

B) Pyruvate kinase

C) Alanine aminotransferase D) Creatinine phosphokinase E) Thrombin

C Alanine aminotransferase

For numbers 29-33, Refer to the structure of this antibacterial agent

29. The functional group in the box is an additional chemical entity of this drug that makes it a prodrug, what is the probable reason of adding that moiety to the parent compound?

A) Increase in absorption

B) Increase in palatability

C) Decrease in Protein binding D) Increase in solubility

E) Decrease in absorption

B Increase in palatability

30. The main functional group of this prodrug is a/an

A) Amide

B) Nitro

C) Alcohol

D) Ester

E) Acyl halide

D Ester

31. When the drug will undergo metabolism, which of the following enzymes will act on it?

A) Ligases

B) Hydrolases C) Transferases D) Isomerases E) Lyases

B Hydrolases

32. When the drug is acted upon by different enzymes during its metabolism, what is/are the products?

A) Alcohol

B) Amide

C) Carboxylic acid D) AandB

E) BandC

B Amide

33. This drug is an example of

A) Cell wall synthesis inhibitor

B) Cell membrane disruptor

C) Protein synthesis inhibitor

D) Nucleic acid synthesis inhibitor

E) Alkylating agent

C Protein synthesis inhibitor

34. The compound use to identify the partition coefficient in-vitro

A) Tert-butyl alcohol

B) Phenol

C) Isopentyl alcohol

D) N-octanol

E) Benzyl alcohol

D N-octanol

35. Isoniazid is metabolized by humans principally by

A) Aceylation

B) Deamination

C) Methylation

D) Conjugation

E) Oxidation

B Deamination

36. The total affinity of the ligand to its receptor

A) Intrinsic activity

B) Agonistic activity

C) Avidity

D) Antagonistic activity

E) Agonistic affinity

C Avidity

37. Dimethylbenzene is also known as

A) Anisole

B) Aniline

C) Xylene

D) Phenol

E) Ethylene

C Xylene

For numbers 38-41, refer to the structure below

38. The type of bond that exists in the structure

A) Amide bond

B) Ether bond

C) Tert-amine bond

D) Ester bond

E) Glycosidic bond

A Amide bond

39. This compound may produce the following effects, except

A) Vasoconstriction

B) Bradycardia

C) Metallic taste

D) CNS depression

E) Sodium channel blockage

A Vasoconstriction

40. The compound is an example of what class of drugs?

A) Anesthetic B) Barbiturate C) Sedatives D) Analgesic E) Anxiolytics

A Anesthetic

41. The absorption of this compound is governed by what equation?

A) Noyes-Whitney equation

B) Fick's Law of Diffusion

C) Beer''s Law

D) Henderson-Hasselbalch equation E) None of the above

D Henderson-Hasselbalch equation

42. This compound is derived from the destructive distillation of castor oil and it is use as a keratolytic agent

A) Salicylic acid

B) Undecylanic acid

C) Benzoic acid

D) Chrysarobin

E) Propionic acid

B Undecylanic acid

43. The following are example of G protein coupled

receptors, except

A) GABA receptors

B) Beta-2 receptors

C) Muscarinic receptors D) Alpha -1 receptors E) Beta -1 receptors

A GABA receptors

44. DNA Alkylating agent binds to its target by means of what bond?

A) Hydrogen bonding

B) Electrostatic bonding C) Hydrophobic bonding D) Ionic bonding

E) Covalent bonding

E Covalent bonding

45. In the presence of a full agonist, a partial agonist becomes

A) Agonist

B) Antagonist

C) Partial agonist D) Inverse agonist E) No effect

B Antagonist

46. A long-acting HMG-CoA reductase inhibitor

A) Rosuvastatin

B) Lovastatin

C) Fluvastatin

D) Simvastatin

E) Pravastatin

A Rosuvastatin

47. This is the most important CYP 450 isozyme that is responsible for the metabolism of almost 50% of the drugs available in the market

A) CYP 2D6

B) CYP 3A4

C) CYP 2A9

D) CYP 1A2

E) CYP 2D10

B CYP 3A4

48. A theory that advances the idea that maximum pharmacologic effect can be obtained if all the receptors are occupied

A) Hypothesis of Paton

B) Lock and Key Theory

C) Hypothesis of Clark

D) Induced fit theory

E) Hypothesis of Ariens & Stephenson

A) Hypothesis of Paton

49. The anti-angina effect of nitrates is primarily due

to the release of what gas?

A) Nitrous oxide

B) Dinitrogen oxide

C) Nitrogen dioxide

D) Nitric oxide

E) Dinitrogen dioxide

D) Nitric oxide

50. Diuretic that acts on the distal convulated tubule

A) Indapamide

B) Furosemide

C) Ethacrinic acid

D) Acetazolamide

E) Spironolactone

A) Indapamide

51. What is 1,4- dihydroxybenzene?

A) Catechol

B) Phenol

C) Xylene

D) Hydroquinone

E) Resorcinol

D) Hydroquinone

52. Halogenation of alkanes is possible in what type of reaction?

A) Substitution

For

B) Elimination

C) Radical reactions

D) Addition

E) Combustion

C) Radical reactions

53. Alkylation of aminobenzene will likely proceed to what position?

A) Ortho position

B) Meta position

C) Para position

D) BothAandB

E) BothAandC

E) BothAandC

54. This is a derivative of two carboxylic acids, in which the compound is formed by the removal of one molecule of water in two RCOOH

A) Ether

B) Acid anhydride

C) Amide

D) Acyl halide

E) Ester

B) Acid anhydride

numbers 55-58, Refer to the structure of Bricanyl®

55. The drug is a derivative of

A) Catechol

B) Phenol

C) Xylene

D) Hydroquinone

E) Resorcinol

E) Resorcinol

56. The compound is not affected by which enzyme during its metabolism?

A) COMT

B) MAO

C) Carboxylases

D) BothAandB

E) BothAandC

A) COMT

57. The compound is a selective agonist of what receptor?

A) Alpha 1

B) M1

C) Beta 1

D) Beta 2

E) N1

D) Beta 2

58. The compound is used to manage

A) Hypertension

B) Asthma

C) Glaucoma

D) Arrhythmia

E) Hypotension

B) Asthma

59. Benzene undergoes what type of reaction?

A) Nucleophilic substitution

B) Electrophilic addition

C) Electrophilic substitution

D) Radical reactions

E) Nucleophilic addition

C) Electrophilic substitution

60. Which of the following carbocation intermediate is the most stable?

A) Primary

B) Secondary

C) Tertiary

D) Quarternary

E) None of the about

C) Tertiary

61. Regioselectivity of an organic reaction in which the orientation of the substituents stabilizes the product is governed by

A) Le Chatelier's Principle

B) Markovnikov's Rule

C) Heck Reaction

D) Hund's Rule

E) Pauli's Principle

B) Markovnikov's Rule

62. An enol is not a stable compound because it undergoes

A) Electrophilic attack

B) Hydrophobic attack

C) Hydrophilic attack

D) Hydrogen shift

E) Tautomerization

E) Tautomerization

For numbers 63-66, refer to the structure of an anxiolytic

drug

63. The affinity of the drug to the

receptor exerts an anxiolytic and hypnotic effects

A) Glutamate

B) Histamine

C) Gamma-aminobutyric acid

D) Glycine

E) Dopamine

C) Gamma-aminobutyric acid

64. The binding affinity of the compound to its receptor is highly influenced by_______ in its structure

A.)Benzene ring

B.) Chloro substituted benzene ring

C.) Carbonyl moiety

D.) Imidazole ring

E.) Seven membered heterocyclic nitrogen ring

B.) Chloro substituted benzene ring

65. Increase the concentration of _______ ions in the cell makes this drug a sedative - hypnotic.

A.) Calcium

B.)Chloride

C.) Phosphate D.) Potassium E.) Sodium

B.)Chloride

66. An essential moiety for this compound to exert its sedative hypnotic effect

A.) Benzene ring

B.) Chloro substituted benzene ring

C.) Carbonyl moiety

D.) Imidazole ring

E.) Seven membered heterocyclic nitrogen ring

E.) Seven membered heterocyclic nitrogen ring

67. The acetylation of morphine yields

A.) Codeine B.) Papaverine C.) Noscapine D.) Heroin

E.) Thebaine

D.) Heroin

68. Primidone is a prodrug that is converted into

A.) Entacapone

B.) Diazepam

C) Phenobarbital D.) Carbamazepine E.) Aminophylline

C) Phenobarbital

For numbers 69-72, Refer to the structure of Zovirax

69. The structure of Zovirax is an analog of

A.)Thymine B.) Adenine C.) Guanosine D.) Uracil

E.) Cytosine

C.) Guanosine

70. What is the difference of the structure of Zovirax to the conventional Nucleic acid base?

A.) It contains a ribose moiety

B.) It contains a deoxyribose moiety

C.) It contains an open sugar moiety

D.) There is a substituted amino group

E.) The hydroxyl group is not attached in the oxygen atom

C.) It contains an open sugar moiety

71. The structure of Zovirax® competitively inhibits what enzyme?

A.) DNA polymerase

B.) Reverse transcriptase C.) Ligase

D.) RNA polymerase

E.) Protease

A.) DNA polymerase

72. Zovirax® is effective against the strain of

A.) Varicella

B.) HSV

C.) Vesicular Slomatitis Virus D.) All of the above

E.) None of the above

D.) All of the above

73. In phenols, substitution at _______ position increases bactericidal activity

A.) Ortho

B.) Meta

C.) Para

D.) All of the above E.) None of the above

C.) Para

74. C3H6O can be a/an

A.) Ketone

B.) Ether

C.) Aldehyde

D.) Both A and B E.) Both A and C

D.) Both A and B

75. Zero order drug metabolism

A.) Saturated Kinetics

B.) Rate of metabolism is in constant concentration C.) Rate of metabolism is not over time due to the presence of enzymes

D.) Dose dependent

E.) Constant fraction of the drug is metabolize

A.) Saturated Kinetics

76. Carbamazepine undergoes what Phase I metabolism reaction?

A.) Aromatic hydroxylation

B.) Olefinic carbon oxidation

C.) Oxidative deamination D.) Allylic carbon oxidation

E.) Reduction of the - OH group

B.) Olefinic carbon oxidation

77. Thiopental is being converted into pentobarbital upon metabolism by what pathway?

A.) Oxidation

B.) Desulfuration

C.) Dealkylation

D.) Reduction

E.) Direct amine conjugation

B.) Desulfuration

78. Which of the following is true about penciclovir?

A.) The structure is similar to acyclovir, except with

the side of oxygen which is replaced by a carbon

and a hydroxyl group

B.) Short half life in tissues compared to acyclovir C.) Competes for the viral RNA Polymerase and inhibits its synthesis

D.) It acts as a chain terminator

E.) All of the above

A.) The structure is similar to acyclovir, except with

the side of oxygen which is replaced by a carbon

and a hydroxyl group

79. The first type of drugs for HIV to be available

A.) NNRTI

B.) NRTI

C.) Entry inhibitors

D.) Protease inhibitors E.) Integrase inhibitors

B.) NRTI

80. Which of the following HIV drugs is also used for Hepatitis B infection?

A.) Azidothymidine B.) Saquinavir

C.) Didanosine

D.) Lamivudine

E.) Efavirenz

D.) Lamivudine

81. Metabolic disorder is commonly seen in what type of HIV drugs?

A.) Integrase inhibitors

B.) Protease inhibitors

C.) NNRTI

D.) NRTI

E.) Entry inhibitors

B.) Protease inhibitors

82. Acylation of the Ring II of aminoglycosides produces ______

A.) Amikacin

B.) Streptomycin C.) Tobramycin D.) Gentamicin

A.) The structure is similar to acyclovir, except with

the side of oxygen which is replaced by a carbon

and a hydroxyl group

E.) Kanamycin

A.) Amikacin

83. Coordination of what metal in tetracycline structure increases its activity?

A.) Iron

B.) Manganese

C.) Cobalt

D.) Palladium

E.) Nickel

D.) Palladium

84. Glycopeptides exert their mechanism of action via

A.) Inhibition of 30s ribosomal subunit

B.) Inhibition of cell wall synthesis

C.) Inhibition of 50s ribosomal subunit D.) Inhibition of DNA gyrase

E.) Inhibition of cell membrane synthesis

B.) Inhibition of cell wall synthesis

85. Which if the following cephalosporins can cross the blood brain barrier?

A.) Cefprozil

B.) Cefuroxime

C.) Cefalexin D.) Cefmetazole E.) Cefazolin

B.) Cefuroxime

86. This agent is used to chelate copper in which an excess amount causes Wilson's disease

A.) EDTA

B.) Dimercaprol C. Penicillamine D.) BAL

E.) Deferoxamine

C. Penicillamine

87. This class of penicillin contains a benzyl moiety that is responsible for its acid labile property

A.) Penicillin V B.) Oxacillin C.) Piperacillin D.) Methicillin E.) Penicillin G

E.) Penicillin G

88. In the Freidles Craft Alkylation of Aromatic rings, what catalyst is needed for the reaction to proceed?

A.) Lewis acid

B.) Bronsted acid C.) Lewis base

D.) Arrhenius base E.) Bronsted base

A.) Lewis acid

89. Sulfonamides are synthetic analogs of:

A.) Gamma aminobutyric acid

B.) Para amino benzoic acid

C.) Tricarboxylic acid

D.) Sulfonic acid

E.) Carbolic acid

B.) Para amino benzoic acid

90. Compounds with two or more chiral centers are termed as

A.) Epimers

B.) Enantiomers

C.) Stereoisomers

D.) Diastereomers

E.) Constitutiona Isomers

D.) Diastereomers

For numbers 91-95, Refer to the structure below

91. This drug may likely bind to what protein?

A.) Albumin

B.) Alpha glycoprotein C.) Ubuquitin

D.) Globulin

E. Bilirubin

A.) Albumin

92. What is the IUPAC name of the drug?

A.) Octanoic acid

B.) 2-propylpentanoic acid

C.) 4-propylpentanoic acid D.) 1-butylbutanoic acid E.) 2-methylheptanoic acid

B.) 2-propylpentanoic acid

93. This drug may likely affects what neurotransmitter?

A.) GABA

B.) Dopamine

C.) Glutamate

D.) Norepinephrine E.) Serotonin

A.) GABA

94. This drug affects what type of ion gated channel?

A.) Sodium

B.) Potassium C.) Calcium D.)BothAandB E.) Both A and C

A.) Sodium

95. This drug is a powerful _____

A.) Antibiotic

B.) Skeletal muscle relaxant C.) Antidepressant

D.) Anticonvulsant

E.) Antipsychotic

D.) Anticonvulsant

96. Insulin Receptors are classified as _______

A.) Ion gated channel receptors

B.) Tyrosine kinase receptors

C.) G- protein coupled receptors

D.) Gene transcription linked receptor E.) Nuclear receptor

B.) Tyrosine kinase receptors

97. The efficacy of salicylic acid as well as its solubility in water as compared to p- hydroxybenzoic acid is greatly affected by what phenomenon?

A.) Dipole movement

B.) Common ion effect

C.) Hydrophobic interactions D.) Hydrogen bonding

E.) Electrostatic forces

D.) Hydrogen bonding

98. The inhibition of the CYP 450 dependent lanosterol 14-alpha demethylase is the main mechanism of action of?

A.) Ketoconazole

B.) Amphotericin B C.) Azelaic acid D.) Griseofulvin E.) Nystatin

A.) Ketoconazole

99.Alkylation of aminobenzene will likely proceed to what position?

A.) Ortho only

B.) Ortho and Meta C.) Meta and Para D.) Para only

E.) Ortho and Para

E.) Ortho and Para

100. An aliphatic phenothiazine derivative

A.) Chlorpromazine

B.) Thiorizadine C.) Fluphenazine D.) Perphenazine E.) Clozapine

A.) Chlorpromazine

101. Decarboxylation of L- Dihydroxyphenylalanine produces

A.) Tyrosine

B.) Epinephrine C.) Ephedrine

D) Dopamine

E.) Norepinephrine

D) Dopamine