DARUNAVIR Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

huzefakifayet — Mon, 04 May 2020 12:07:36 +0000

Darunavir

IUPAC nomenclature

[(1R,5S,6R)-2,8-dioxabicyclo[3.3.0]oct-6-yl] N-[(2S,3R)-4- [(4-aminophenyl)sulfonyl- (2-methylpropyl)amino]-3-hydroxy-1-phenyl- butan-2-yl] carbamate

Classification

Darunavir is an HIV protease inhibitor.

Physiochemical Properties

S. NO.	PHYSICAL AND CHEMICAL PROPERTIES
1	Molecular weight	547.7 g/mol
2	Physical appearance	White amorphous solid
3	Melting point	74°C
4	Solubility	8.7 mg/L in water
5	Octanol/water partition coefficient	1.8
6	Presence of ring	Furan, phenyl
7	Number of chiral centers	4

Mechanism of Action

Darunavir binds with HIV-1 protease enzyme and prevents the HIV replication through halting the dimerization and catalytic activity of HIV-1 protease. It specifically inhibits the cleavage of HIV encoded Gag-Pol proteins in cells, which ceases the generation of the mature virus particle and thus checks the spread of infection.

Structure Activity Relationship

Darunavir have activity against multi-drug resistant strains of HIV-1.
It is having high affinity binding to the N-H groups of P2 pocket of the HIV-1 protease.
The large portion of the drug rest on the substrate envelope. [1]

Method of synthesis

i. Isobutylamine is reacted with protected (2S,3S)-1,2-epoxy-3-amino-4-phenylbutane.

ii. The reaction is followed by reaction with p-nitrobenzenesulfonyl chloride in the presence of the base to get protected N-((2R,3S)-3-amino-2hydroxy-4-phenylbutyl)-/V-isobutyl-4-nitro-benzenesulfonamide.

iii. Reducing the formed compound and hydrolyzing.

iv. Coupling of the compound with (3R, 3aS, 6aR)-hexahydrofuro[2,3-6]furan-3-ol derivative to get darunavir. [2]

Therapeutic Uses

Darunavir is used for the treatment and prevention of HIV infection.

Side Effects

Side effects of Darunavir are:

Nausea
Headache
Vomiting
Stomach pain

MCQs

Q.1 What can be the brand name for drug Darunavir?

a) Otogesic

b) Prezista

c) Nupercaine

d) Bendzon

Q.2 Therapeutic use of Darunavir is?

a) Treatment of HIV

b) Treatment of Anxiety

c) Treatment of diabetes

d) Treatment of cancer

Q.3 Type of ring present in the structure of Darunavir?

I. Phenyl

II. Purine

III. Pyridine

IV. Furan

a) I, III

b) II, III

c) I, IV

d) II, IV

Q.4 Side effects of drug Darunavir is/are?

a) Nausea

b) Headache

c) Vomiting

d) All of the above

Q.5 Match the following drugs with their correct molecular weights-

i. Darunavir	A. 312 gm/mol
ii. Oseltamivir	B. 332 gm/mol
iii. Zanamivir	C. 547.7 gm/mol
iv. Ribavirin	D.244 gm/mol

a) i-C, ii-A, iii-B, iv-D

b) i-D, ii-B, iii-C, iv-A

c) i-B, ii-A, iii-D, iv-C

d) i-A, ii-B, iii-C, iv-D

Q.6 An example of drug from class HIV protease inhibitor is?

a) Amprenavir

b) Darunavir

c) Atazanavir

d) All of the above

Q.7 Number of chiral centers present in the structure of darunavir?

a) 4

b) 1

c) 2

d) 3

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ANSWERS

1-b

2-a

3-c

4-d

5-a

6-d

7-a

REFERENCES

[1] http://www.antimicrobe.org/d94.asp

[2] VardanyaVellanki SR, Sahu A, Katukuri AK, Vanama V, Kothari S, Ponnekanti VS, Datta D, inventors; Mylan Laboratories Ltd, assignee. Process for the preparation of darunavir. United States patent US 8,703,980. 2014 Apr 22.n R, Hruby V. Antiviral Drugs. Synthesis of Best-Seller Drugs. 2016:687.

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