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

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

Dexlansoprazole

IUPAC nomenclature

(R)-(+)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole

Classification

  • Proton pump inhibitors

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 369.4  g/mol
2 Physical appearance White to brownish-white crystalline powder
3 Melting point 140oC
4 Solubility 0.21 mg/ml
5 Octanol/water partition coefficient 2.38
5 Presence of ring Pyridine. Benzimidazole
6 Number of chiral centers Not present

 

 

Mechanism of Action

  • Dexlansoprazole is a prodrug which requires protonation via an acidic environment to get activated form Sulphenamide.
  • Sulphenamide covalently binds with cystien residues via disulfide bridges on the α subunit of H/K ATPase enzyme system.
  • Thereby it inhibits the H+/K+ ATPase pump which in turn inhibits the gastric acid secretion or formation of hydrochloric acid in parietal cells

 

Structure Activity Relationship

General structure activity of Heteroaryl- and heterocyclyl-substituted imidazo[1,2-a]Pyridine derivatives acting as acid pump antagonists can be summarized as:

  • The inhibitory property of drugs depends on hydrophobic group substituted at the left side ortho-position of the phenyl ring.
  • Increase in hydrophobic value increases the activity.
  • Increasing the GTCI value decreases the activity.
  • Small molecule substitutions may participate in hydrophobic interaction as well as steric interactions. [1]

 

Method of synthesis

TAP’s group synthesized the Dexlansoprazole through the following scheme: [2]

Medicinal Uses

Dexlansoprazole is used for treatment of:

  • Stomach ulcers
  • Active duodenal ulcers
  • Active benign gastric ulcer
  • GERD
  • Erosive esophagitis
  • Zollinger-Errison syndrome

 

Side Effects

Side effects of Dexlansoprazole are:

  • Abdominal pain
  • Nausea
  • Constipation
  • Headache
  • Low magnesium blood level
  • Irregular heartbeat
  • Muscle spasms
  • Seizures
  • Lupus
  • Diarrhea
  • Blood in stool

 

 

MCQs

Q.1 Mechanism of action of Dexlansoprazole drug includes?

a) Protonation into sulphenamide

b) Conversion into hydroxyzine

c) Vasoconstriction

d) Agonist effects H1 receptor for Histamine

Q.2 Medicinal use of drug Dexlansoprazole is/are?

a) Stomach ulcers

b) Watery eyes

c) Sneezing

d) Hives

Q.3 Select the correct option from below related with the General structure activity of Heteroaryl- and heterocyclyl-substituted imidazo[1,2-a]Pyridine derivatives acting as acid pump antagonists-

a) The inhibitory property of drugs depends on hydrophobic group substituted at the left side ortho-position of the phenyl ring.

b) Increase in hydrophobic value decreases the activity.

c) Increasing the GTCI value increases the activity.

d) All of the above

Q.4 Number of chiral carbons present in the structure of Dexlansoprazole is?

a) 0

b) 1

c) 2

d) 3

Q.5 Correct sequence for the True/False for the physiochemical properties of the drug dexlansoprazole can be?

  • Molecular weight: 952.3 gm/mol
  • Physical appearance: Yellow crystalline powder
  • Octanol/water partition coefficient: 2.38

a) TTT

b) TFT

c) FFT

d) TFF

Q.6 Correct statements for the IUPAC nomenclatures of the drugs are?

I. Dexlansorazole: 2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

II. Loxapine: (3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole.

III. Gluthethmide: 4-Chlorophenyl)phenylmethyl-1-piperazinyl]ethoxy]acetic acid

IV. Tolazoline: 2-Benzyl-4,5-dihydro-1H-imidazole

a) I, II

b) III, IV

c) IV

d) I, II, III, IV

Q.7 Match the following drugs with their correct classifications-

i. Dexlansoprazole A. Proton pump inhibitor
ii. Ibuprofen B. Sedative-hypnotic
iii. Naloxone C. Anti-inflammatory
iv. Chlordiazepoxide D. Narcotic antagonist

 a) i-A, ii-C, iii-D, iv-B

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

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

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

 

 

 

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ANSWERS

1-a

2-a

3-a

4-a

5-c

6-c

7-a

 

REFERENCES

[1] Agarwal N, Bajpai A, Gupta SP. A quantitative structure-activity relationship and molecular modeling study on a series of heteroaryl-and heterocyclyl-substituted imidazo [1, 2-a] pyridine derivatives acting as acid pump antagonists. Biochemistry Research International. 2013 Jan 1;2013.

[2] Raju MN, Kumar NU, Reddy BS, Anitha N, Srinivas G, Bhattacharya A, Mukkanti K, Kolla N, Bandichhor R. An efficient synthesis of dexlansoprazole employing asymmetric oxidation strategy. Tetrahedron letters. 2011 Oct 19;52(42):5464-6.

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