Introduction to Organic Medicinal Chemistry

The practice of medicinal chemistry devoted to the discovery and development of new drugs

a. Organic chemistry

b. Inorganic chemistry

c. Organic biochemistry

d. Organic medicinal chemistry

d. Organic medicinal chemistry

Receptor is a relatively small region of macromolecule which can be:

a. Isolatable enzyme

b. Structural or functional component of cell membrane

c. Specific intracellular substances

d. a and c

e. All

e. All

What is the most stable form of morphine to bind to the mu receptor?

a. T-shaped conformation

b. L-shaped conformation

c. S-shaped conformation

d. R-shaped conformation

a. T-shaped conformation

What is the chemical bonding involved between protamine and heparin?

a. Neutralization

b. Oxidation

c. Reduction

d. Hydrolysis

a. Neutralization - specifically neutralization reaction

Selection of structural components, the steric, electronic, and solubility characteristics of a drug which makes it interchangeable with drugs of the same pharmacologic class.

a. Isomerism

b. Isosterism

c. Sterioisomerism

d. Geometric isomerism

b. Isosterism

Interchangeability of one molecule with another molecule.

a. Isomerism

b. Isosterism

c. Sterioisomerism

d. Geometric isomerism

b. Isosterism

Basis for alteration of pharmacokinetic and pharmacologic properties of drugs.

a. Isomerism

b. Isosterism

c. Sterioisomerism

d. Geometric isomerism

b. Isosterism

Compounds or group of atoms having the same number of arrangement of electrons.

a. Isomers

b. Isobars

c. Isotones

d. Isosteres

d. Isosteres

Concepts under SAR except:

a. Part responsible for mechanism of action

b. Part responsible for increased absorption

c. Part mainly metabolized

d. Part responsible for prolonged or shortened duration of action

e. None

e. None

R−N=N−R′

a. Azo

b. Hydrazo

c. Azido

d. Nitroso

e. Nitro

a. Azo

R−N-N−R′

a. Azo

b. Hydrazo

c. Azido

d. Nitroso

e. Nitro

b. Hydrazo

⁻N=N⁺=N⁻

a. Azo

b. Hydrazo

c. Azido

d. Nitroso

e. Nitro

c. Azido

N=O

a. Azo

b. Hydrazo

c. Azido

d. Nitroso

e. Nitro

d. Nitroso

-NO2

a. Azo

b. Hydrazo

c. Azido

d. Nitroso

e. Nitro

e. Nitro

HO-C-NH2

a. Hydroxylamine

b. Carbinolamine

c. Sulfoxide

d. Sulfone

e. Sulfonamide

b. Carbinolamine

HO-NH2

a. Hydroxylamine

b. Carbinolamine

c. Sulfoxide

d. Sulfone

e. Sulfonamide

a. Hydroxylamine

S=O

a. Hydroxylamine

b. Carbinolamine

c. Sulfoxide

d. Sulfone

e. Sulfonamide

c. Sulfoxide

O=S=O

a. Hydroxylamine

b. Carbinolamine

c. Sulfoxide

d. Sulfone

e. Sulfonamide

d. Sulfone

R−S(=O)2−NR'R"

a. Hydroxylamine

b. Carbinolamine

c. Sulfoxide

d. Sulfone

e. Sulfonamide

e. Sulfonamide

NC=OO

a. Carbamate

b. Urea

c. Guanidine

d. Sulfonamide

a. Carbamate

NC=ON

a. Carbamate

b. Urea

c. Guanidine

d. Sulfonamide

b. Urea

NC=NN

a. Carbamate

b. Urea

c. Guanidine

d. Sulfonamide

c. Guanidine

Nomenclature of heterocyclic compounds:

a. Hantzsch-Widman nomenclature

b. Common names

c. Replacement nomenclature

d. a and b

e. All

e. All

Oxiranes is an example of:

a. Hantzsch-Widman nomenclature

b. Common names

c. Replacement nomenclature

d. a and b

e. All

a. Hantzsch-Widman nomenclature

Ethylene oxide:

a. Hantzsch-Widman nomenclature

b. Common names

c. Replacement nomenclature

d. a and b

e. All

b. Common names

Oxacyclopropane:

a. Hantzsch-Widman nomenclature

b. Common names

c. Replacement nomenclature

d. a and b

e. All

c. Replacement nomenclature

Hantzsch-Widman nomenclature prefix for O.

a. Oxa-

b. Aza-

c. Thia-

d. Phospha-

a. Oxa-

Hantzsch-Widman nomenclature prefix for N.

a. Oxa-

b. Aza-

c. Thia-

d. Phospha-

b. Aza-

Hantzsch-Widman nomenclature suffix for 5-membered heterocyclic compound.

a. ir

b. et

c. ol

d. in

e. ep

c. ol

Hantzsch-Widman nomenclature suffix for 6-membered heterocyclic compound.

a. ir

b. et

c. ol

d. in

e. ep

d. in

Hantzsch-Widman nomenclature suffix for 6-membered saturated heterocyclic compound.

a. irane

b. etane

c. olane

d. inane

e. epane

d. inane

Hantzsch-Widman nomenclature suffix for 5-membered saturated heterocyclic compound with nitrogen.

a. iridine

b. etidine

c. olidine

d. inane

e. epane

c. olidine

True about drug metabolism except:

a. Aim is to convert drug to polar, pharmacologically inactive, and excretable form

b. Some drugs are extensively metabolized

c. Most drug absorbed are lipophilic

d. All metabolites are detoxified or inactivated

e. None

d. All metabolites are detoxified or inactivated

NOT ALL.

The following undergo extensive first pass effect except:

a. Lidocaine

b. Nitrates

c. Morphine

d. Meperidine

e. None

e. None

Phenol hydrogen sulfate from metabolism of phenol:

a. Inactive

b. Similar activity to the drug

c. Different activity

d. Toxic metabolite

a. Inactive

Temazepam from hydroxylation of diazepam:

a. Inactive

b. Similar activity to the main drug

c. Different activity

d. Toxic metabolite

b. Similar activity to the main drug

Oxazepam from N-demethylation of Temazepam:

a. Inactive

b. Similar activity to the main drug

c. Different activity

d. Toxic metabolite

b. Similar activity to the drug

Isoniazid from N-Dealkylation of Ipronazid:

a. Inactive

b. Similar activity to the drug

c. Different activity

d. Toxic metabolite

c. Different activity

Phenetidine from metabolism of Phenacetin:

a. Inactive

b. Similar activity to the drug

c. Different activity

d. Toxic metabolite

d. Toxic metabolite

N-hydroxy phenacetin from metabolism of phenacetin:

a. Inactive

b. Similar activity to the drug

c. Different activity

d. Toxic metabolite

d. Toxic metabolite

Can be responsible for hepatotoxicity:

a. Phenacetin

b. N-hydroxy phenacetin

c. Phenetidine

d. Diazepam

b. N-hydroxy phenacetin

Can be responsible for methemoglobinemia:

a. Phenacetin

b. N-hydroxy phenacetin

c. Phenetidine

d. Diazepam

c. Phenetidine

Functionalization phase of metabolism:

a. Phase I

b. Phase II

a. Phase I

Polar functional group introduced during phase I metabolism except:

a. OH

b. COOH

c. NH2

d. SH

e. None

e. None

Enzyme system involved during phase I metabolism except:

a. Mixed function oxidases

b. Monooxygenases

c. CYP450

d. CYP3A4

e. None

e. None

Mixed function oxidases is aka monooxygenases or CYP450

Most dominant enzyme system involved during phase I metabolism.

a. CYP450

b. CYP3A4

c. MAO

d. COMT

a. CYP450

Dominant enzyme system involved during phase I metabolism inhibited by grapefruit.

a. CYP450

b. CYP3A4

c. MAO

d. COMT

b. CYP3A4

Mechanism of functionalization during phase I metabolism:

a. Direct introduction

b. Unmasking

c. Demethylation

d. a and b

e. b and c

f. All

f. All

Demethylation is an example of unmasking.

Phase I metabolism reactions:

a. Oxidation

b. Reduction

c. Hydrolysis

d. a and b

e. b and c

f. All

f. All

Most common phase I metabolism reaction.

a. Oxidation

b. Reduction

c. Hydrolysis

a. Oxidation

Phase I metabolism reaction for carboxylic acid derivatives.

a. Oxidation

b. Reduction

c. Hydrolysis

c. Hydrolysis

The following undergo oxidation except:

a. Alcohols

b. Aldehydes

c. Olefins

d. Aromatic moieties

e. None

e. None

Product of oxidation of 1° alcohol.

a. Aldehdye

b. Epoxide

c. Ketone

d. Arenol

e. Salt

a. Aldehyde

Product of oxidation of 2° alcohol.

a. Carboxylic acid

b. Epoxide

c. Ketone

d. Arenol

e. Salt

c. Ketone

Product of oxidation of aldehyde under acidic condition.

a. Carboxylic acid

b. Epoxide

c. Ketone

d. Arenol

e. Salt

a. Carboxylic acid

Product of oxidation of aldehyde under alkali condition.

a. Carboxylic acid

b. Epoxide

c. Ketone

d. Arenol

e. Salt

e. Salt

Product of oxidation of olefin.

a. Carboxylic acid

b. Epoxide

c. Ketone

d. Arenol

e. Salt

b. Epoxide

Product of oxidation of arenes.

a. Carboxylic acid

b. Epoxide

c. Ketone

d. Arenol

e. Salt

d. Arenol

Oxidation of arenes at what position will produce arenol which usually favors excretion?

a. Meta

b. Ortho

c. Para

d. Any

c. Para

Undergo reduction reaction except:

a. Aldehydes

b. Ketones

c. Azo groups

d. Nitro grouos

e. Disulfides

f. None

f. None

Product of reduction of ketone.

a. 1° alcohol

b. 2° alcohol

c. Amine

d. Thiol

b. 2° alcohol

Product of reduction of aldehyde.

a. 1° alcohol

b. 2° alcohol

c. Amine

d. Thiol

a. 1° alcohol

Conversion of chloral hydrate to trichloroethanol involved what reaction?

a. Oxidation

b. Reduction

c. Hydrolysis

b. Reduction

chloral hydrate (aldehdye) to trichloroethanol (1° alcohol)

Trichloroethanol is still active which can act as sedative hypnotic.

a. True

b. False

a. True

Chloral hydrate is a date rape drug.

a. True

b. False

a. True

Product of reduction of disulfide.

a. 1° alcohol

b. 2° alcohol

c. Amine

d. Thiol

d. Thiol

Final product of reduction of azo and nitro group.

a. 1° alcohol

b. 2° alcohol

c. Amine

d. Thiol

c. Amine

Product of reduction of azo group.

a. Nitroso

b. Hydroxylamine

c. Hydrazo

d. Amine

c. Hydrazo

Product of reduction of hydrazo group.

a. Nitroso

b. Hydroxylamine

c. Azo

d. Amine

d. Amine

Product of reduction of nitro group.

a. Nitroso

b. Hydroxylamine

c. Hydrazo

d. Amine

a. Nitroso

Product of reduction of nitroso group.

a. Nitro

b. Hydroxylamine

c. Hydrazo

d. Amine

b. Hydroxylamine

Product of reduction of hydroxylamine group.

a. Nitro

b. Nitroso

c. Hydrazo

d. Amine

d. Amine

Major pathway for acid derivatives.

a. Oxidation

b. Reduction

c. Hydrolysis

c. Hydrolysis

Reaction involved in metabolism of aspirin to salicylic acid and acetic acid.

a. Oxidation

b. Reduction

c. Hydrolysis

c. Hydrolysis

Reaction involved in metabolism of procaine to para-aminobenzoic acid (PABA).

a. Oxidation

b. Reduction

c. Hydrolysis

c. Hydrolysis

Reaction involved in metabolism of prednisone to prednisolone.

a. Oxidation

b. Reduction

c. Hydrolysis

b. Reduction

Phase of metabolism with goal to attach small , polar, ionizable endogenous compounds to functional handles produce water soluble conjugated products.

a. Phase II

b. Conjugation phase

c. Synthetic phase

d. a and b

e. b and c

f. All

f. All

Phase II metabolism reaction that do not necessarily increase water solubility.

a. Methylation

b. Acetylation

c. Glutathione conjugaion

d. a and b

e. b and c

f. All

f. All

Terminate or attenuate biologically activity and not generally increase water solubility.

a. Methylation

b. Acetylation

c. Glutathione conjugaion

d. a and b

e. b and c

f. All

d. a and b

Methylation

Acetylation

Protect the body against chemically active compounds and metabolites.

a. Methylation

b. Acetylation

c. Glutathione conjugaion

d. a and b

e. b and c

f. All

c. Glutathione conjugaion

Phase II reactions except:

Glucuronidation

Sulfation

Glycine/Glutamine conjugation

Acetylation

Methylation

Glutathione conjugation

a. Glucuronidation

b. Sulfation

c. Methylation

d. Glutathione conjugation

e. None

e. None

Most common phase II reaction.

a. Glucuronidation

b. Sulfation

c. Methylation

d. Glutathione conjugation

e. None

a. Glucuronidation

Not yet developed in neonates.

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

a. Glucuronidation

Substrate are:

Alcohols

Phenols

Carboxylic acids

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

a. Glucuronidation

Substrate are mostly phenols.

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

b. Sulfation

Substrate are:

Glycine: aromatic acid and arylalkyl acids

Glutamine: aryl acetic acids

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

c. Glycine/Glutamine conjugation

Substrate are:

1° amines

Aromatic amines

Sulfonamides

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

d. Acetylation

Substrate are endogenous biogenic amines.

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

e. Methylation

Substrate are electrophilic reactive species.

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

f. Glutathione conjugation

Enzyme and cofactor for glucuronidation.

a. UDP-glucuronosyl acetyltransferases (UDP-glucuronic acid)

b. Sulfotransferases (3'Phosphoadenosyl-5'-phosphosulfate [PAPS])

c. N-acyl transferase (Gly,Glu)

d. N-acetyltransferase (Acetyl-CoA)

e. Methyltransferase (S-adenosylmethionine [SAM])

f. S-transferase (GSH)

a. UDP-glucuronosyl acetyltransferases (UDP-glucuronic acid)

Enzyme and cofactor for sulfation.

a. UDP-glucuronosyl acetyltransferases (UDP-glucuronic acid)

b. Sulfotransferases (3'Phosphoadenosyl-5'-phosphosulfate [PAPS])

c. N-acyl transferase (Gly,Glu)

d. N-acetyltransferase (Acetyl-CoA)

e. Methyltransferase (S-adenosylmethionine [SAM])

f. S-transferase (GSH)

b. Sulfotransferases (3'Phosphoadenosyl-5'-phosphosulfate [PAPS])

Enzyme and cofactor for glycine and glutamine conjugation.

a. UDP-glucuronosyl acetyltransferases (UDP-glucuronic acid)

b. Sulfotransferases (3'Phosphoadenosyl-5'-phosphosulfate [PAPS])

c. N-acyl transferase (Gly,Glu)

d. N-acetyltransferase (Acetyl-CoA)

e. Methyltransferase (S-adenosylmethionine [SAM])

f. S-transferase (GSH)

c. N-acyl transferase

Enzyme and cofactor for glutathione.

a. UDP-glucuronosyl acetyltransferases (UDP-glucuronic acid)

b. Sulfotransferases (3'Phosphoadenosyl-5'-phosphosulfate [PAPS])

c. N-acyl transferase (Gly,Glu)

d. N-acetyltransferase (Acetyl-CoA)

e. Methyltransferase (S-adenosylmethionine [SAM])

f. S-transferase (GSH)

f. S-transferase

Enzyme and cofactor for methylation.

a. UDP-glucuronosyl acetyltransferases (UDP-glucuronic acid)

b. Sulfotransferases (3'Phosphoadenosyl-5'-phosphosulfate [PAPS])

c. N-acyl transferase (Gly,Glu)

d. N-acetyltransferase (Acetyl-CoA)

e. Methyltransferase (S-adenosylmethionine [SAM])

f. S-transferase (GSH)

e. Methyltransferase (S-adenosylmethionine [SAM])

Enzyme and cofactor for acetylation.

a. UDP-glucuronosyl acetyltransferases (UDP-glucuronic acid)

b. Sulfotransferases (3'Phosphoadenosyl-5'-phosphosulfate [PAPS])

c. N-acyl transferase (Gly,Glu)

d. N-acetyltransferase (Acetyl-CoA)

e. Methyltransferase (S-adenosylmethionine [SAM])

f. S-transferase (GSH)

d. N-acetyltransferase (Acetyl-CoA)

Reaction undergone by:

Paracetamol

Chloramphenicol

Bilirubin

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

a. Glucuronidation

Reaction undergone by benzoic acid.

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

c. Glycine/Glutamine conjugation

Main reaction undergone paracetamol in neonates.

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

b. Sulfation

Reaction undergone by:

Hydralazine

Isoniazid

Procainamide

Sulfonamide

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

d. Acetylation

Reaction important to relieve paracetamol poisoning

a. Glucuronidation

b. Sulfation

c. Glycine/Glutamine conjugation

d. Acetylation

e. Methylation

f. Glutathione conjugation

f. Glutathione conjugation