Medicinal Chemistry - - Unit 12 - Week 9 https://onlinecourses-archive.nptel.ac.in/noc19_...

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Unit 12 - Week 9
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Certification exam Assignment 9
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outline
assignment.

How to access 1) Lidocaine is a longer lasting local anaesthetic than procaine because 1 point
the portal procaine has an ester group which is susceptible to hydrolysis whereas
lidocaine has an amide group that is resistant to hydrolysis.
About IISER
Pune

Pre-Requisite
True
Assignment
False
Week 1
No, the answer is incorrect.
Week 2 Score: 0
Accepted Answers:
Week 3 True
2) Esters are frequently used as prodrugs because esters are more 1 point
Week 4
susceptible to hydrolysis if the alcohol moiety has an electron donating
Week 5 group.

Week 6 True
False
Week 7
No, the answer is incorrect.
Week 8 Score: 0
Accepted Answers:
Week 9 False
Quiz : 3) Structures (I) and (II) are prodrugs of the antibiotic chloramphenicol. 1 point
Assignment 9 Structure (II) is more water soluble than chloramphenicol and is used to
Optimizing achieve higher concentrations for injections. Structure (I) has lower water
Access to the solubility, as a result it reduces the bitter taste of the drug when given by
Target mouth.
Prodrugs

Prodrugs and
Drug Alliances © 2014 NPTEL - Privacy & Terms - Honor Code - FAQs -
True
A project of
Endogenous In association with
False
Compounds,
Peptidomimetics No, the answer is incorrect.
and
Score: 0 Funded by
Oligonucleotides
as Drugs

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Medicinal Chemistry - - Unit 12 - Week 9 https://onlinecourses-archive.nptel.ac.in/noc19_...

Accepted Answers:
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Tutorial 13-
Optimizing
False
Access-
4) The term ‘prodrugs’ is used for some drugs containing an ester 1 point
Prodrugs
group that are inactive in vitro, but are active once the drug has been
Medicinal absorbed in vivo.
Chemistry :
Week 9
True
Feedback form
False
Week 10
No, the answer is incorrect.
Week 11 Score: 0
Accepted Answers:
Week 12 True

Download 5) The structure of codeine is illustrated below. It is a prodrug of 1 point

videos morphine.

TRANSCRIPTS

Interaction True
Session
False
No, the answer is incorrect.
Score: 0
Accepted Answers:
True
6) In Parkinson's disease, there is a lack of the neurotransmitter 1 point
dopamine in the brain. Adding dopamine itself is not very effective because
dopamine cannot access the brain easily, rapidly metabolized and shows
poor selectivity between different types of dopaminergic receptors.

True
False
No, the answer is incorrect.
Score: 0
Accepted Answers:
True
7) Phosphate drugs are less polar in nature than their parent drugs. 1 point

True
False
No, the answer is incorrect.
Score: 0
Accepted Answers:
False
8) L791456 is an anti-arthritic drug with a shorter lifetime in the body 1 point
than L787257. The only difference in the structures is a methyl substituent on
one of the pyridine rings. Why does the presence of a methyl group decrease
the lifetime of the drug?

It is metabolized by oxidative enzymes to an alcohol or carboxylic

acid. The resulting polar metabolites are rapidly excreted
It increases the rate of N-oxidation and deactivation of the drug

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Medicinal Chemistry - - Unit 12 - Week 9 https://onlinecourses-archive.nptel.ac.in/noc19_...

It acts as a steric shield and hinders the drug binding to its target
It increases the basicity of the pyridine ring causing it to bind to
plasma proteins
No, the answer is incorrect.
Score: 0
Accepted Answers:
It is metabolized by oxidative enzymes to an alcohol or carboxylic acid. The
resulting polar metabolites are rapidly excreted
9) Tioconazole is a non-polar antifungal agent which is used topically, 1 point
whereas fluconazole is a polar drug which is used systemically. Which of the
following statements is correct?

The fluorine substituents in fluconazole increase water solubility

Increased polarity decreases water solubility
The alcohol group in fluconazole increases polarity
The heterocyclic groups in fluconazole contain more nitrogen atoms
making the drug less polar
No, the answer is incorrect.
Score: 0
Accepted Answers:
The alcohol group in fluconazole increases polarity
10)Losartan was developed from structure (I) as an antihypertensive 1 point
agent by replacing a carboxylic acid group with a tetrazole ring. Which of the
following statements is incorrect?

The tetrazole ring is more polar than carboxylic acid

The tetrazole ring represents a bio-isostere
The tetrazole ring mimics a carboxylic acid in being planar
The tetrazole ring mimics a carboxylic acid in being acidic
No, the answer is incorrect.
Score: 0
Accepted Answers:
The tetrazole ring is more polar than carboxylic acid
11)Some peptides and proteins have been used as drugs. Which of the 1 point
following statements is not true?

Peptide drugs are susceptible to metabolic enzymes but not to

digestive enzymes
Peptide drugs are susceptible to peptidase enzymes
Peptides and proteins generally show poor bioavailability
Protein drugs suffer a disadvantage in that they could produce an
immune response
No, the answer is incorrect.
Score: 0
Accepted Answers:
Peptide drugs are susceptible to metabolic enzymes but not to digestive

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Medicinal Chemistry - - Unit 12 - Week 9 https://onlinecourses-archive.nptel.ac.in/noc19_...

enzymes
12)Why does chlorpropamide have a longer antibiotic activity than 1 point
tolbutamide?

The chloro group of chlorpropamide has an electron-withdrawing

effect on the aromatic ring and stabilises the molecule.
The methyl group of tolbutamide is susceptible to drug metabolism
whereas the chloro substituent of chlorpropamide is not
The urea group of tolbutamide is more susceptible to hydrolysis than
the urea group of chlorpropamide
The sulfonamide group of tolbutamide is more susceptible to
hydrolysis than the sulfonamide group of chlorpropamide
No, the answer is incorrect.
Score: 0
Accepted Answers:
The methyl group of tolbutamide is susceptible to drug metabolism whereas the
chloro substituent of chlorpropamide is not
13)Fluphenazine decanoate is an ester prodrug for the antipsychotic 1 point
drug fluphenazine, and is administered by intramuscular injection. Which of
the following statements is true?

Hydrolysis of the ester reveals a carboxylic acid group on the

fluphenazine
The ester is hydrophilic and rapidly enters the blood supply.
The ester is rapidly hydrolyzed in blood since the pH of blood is
slightly alkaline
The ester is hydrophobic which means that it is taken up in fat tissue.
As a result, it can only enter the blood supply at a slow rate
No, the answer is incorrect.
Score: 0
Accepted Answers:
The ester is hydrophobic which means that it is taken up in fat tissue. As a
result, it can only enter the blood supply at a slow rate
14)Candoxatril is an ester prodrug for candoxatrilat which inhibits 1 point
protease enzymes. Which of the following statements is incorrect?

Hydrolysis of the ester reveals a carboxylic acid group on

candoxatrilat
The bicyclic leaving group is non-toxic
The parent drug can be administered orally, whereas the ester
prodrug cannot
The bicyclic system is electron withdrawing and speeds up the rate of
ester hydrolysis
No, the answer is incorrect.
Score: 0
Accepted Answers:

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Medicinal Chemistry - - Unit 12 - Week 9 https://onlinecourses-archive.nptel.ac.in/noc19_...

The parent drug can be administered orally, whereas the ester prodrug cannot
15)Carbachol is more stable than acetylcholine to hydrolysis. Which of 1 point
the following statements is not true?

The blue coloured methyl group of acetylcholine is susceptible to

oxidation by cytochrome P450 enzymes
The blue coloured nitrogen of carbachol stabilizes the neighbouring
carbonyl group
Carbachol contains a urethane group while acetylcholine contains an
ester group
The blue coloured NH2 group of carbachol is a bio-isostere for the blue
coloured CH3 group of acetylcholine

No, the answer is incorrect.

Score: 0
Accepted Answers:
The blue coloured methyl group of acetylcholine is susceptible to oxidation by
cytochrome P450 enzymes
16)Which of the following strategies will increase the polarity and water 1 point
solubility of a drug?

Adding extra alkyl groups

Removing polar functional groups
Replacing an alkyl group with a larger alkyl group
Replacing an aromatic ring with a nitrogen containing heterocyclic
ring
No, the answer is incorrect.
Score: 0
Accepted Answers:
Replacing an aromatic ring with a nitrogen containing heterocyclic ring

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