SODIUM SALICYLATE Synthesis, SAR, MCQ, Structure,Chemical Properties and Therapeutic Uses

Sodium salicylate

IUPAC nomenclature

Sodium;2-hydroxybenzoate

Classification

  • Non-selective COX inhibitors (traditional NSAIDs)
  • Salicylates

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 160.1g/mol
2 Physical appearance Dry powder or liquid
3 Melting point 200°C
4 Solubility 0.78 M
5 Octanol/water partition coefficient logP = -1.43
6 Presence of ring Phenyl
7 Number of chiral centers Not present

 

Mechanism of Action

  • Sodium salicylate inhibits release of prostaglandin E2 when added together with interlukin 1ß
  • It also causes a concentration-dependent inhibition of COX-2 activity. [1]

 

Structure Activity Relationship

SAR for salicylates can be summarized as follows:

  • Active moiety responsible for the action is salicylate anion.
  • Side effects of the drug are associated with carboxylic acid function.
  • Reducing the acidity of carboxylic acid by converting into amide maintains the analgesic action but eliminates the anti-inflammatory properties.
  • Substitution on the carboxyl or phenyl hydroxyl groups results in changes in the toxicity and potency of the drug.
  • Activity is abolished when the phenolic hydroxyl group is placed on meta or para position to the carboxyl group.
  • Introduction of the halogen atom on the phenolic ring increases the potency and the toxicity of the drug.
  • Substitution on the 5th-position on the phenolic ring increases the anti-inflammatory property of the drug. [2]

 

Method of synthesis

Sodium salicylate is prepared from sodium phenolate and carbon dioxide under higher temperature and pressure.

 

Therapeutic Uses

Sodium salicylate is used for:

  • Treatment of acne vulgaris
  • Treatment of psoriases
  • Treatment of warts
  • Treatment of scalp dermatoses
  • Treatment of dermatitis seborreic

 

 Side Effects

Side effects Sodium salicylate are:

  • Nausea
  • Vomiting
  • Excess stomach acid secretion
  • Heartburn
  • Stomach cramps
  • Irritation in stomach and intestines
  • Rupture of wall of stomach or intestine
  • Allergic reaction
  • Rash
  • Hemolytic anemia
  • Anemia
  • Bleeding in stomach
  • Bronchospasm,
  • Itching
  • Wheezing
  • Trouble breathing
  • Stomach or intestinal ulcers
  • Hives
  • Skin redness

 

MCQs

Q.1 Choose the correct option related with the mechanism of action of drug Sodium salicylate?

a) Inhibits release of Prostaglandin E2

b) It stimulates the activity of COX-2

c) It stimulates the activity of COX-1

d) All of the above

Q.2 Medicinal use of drug Sodium salicylate is/are?

a) Treatment of acne ulgaris

b) Treatment of psoriases

c) Treatment of warts

d) All of the above

Q.3 Which amongst the following are the correct statements with respect to the SAR of drug Sodium salicylate?

I. Active moiety responsible for the action is salicylate anion.

II. Side effects of the drug is associated with carboxylic acid function.

III. Reducing the acidity of carboxylic acid by converting into amide maintain the analgesic action but increase the anti-inflammatory properties.

IV. Substitution on the carboxyl or phenyl hydroxyl groups results in changes in the toxicity and potency of the drug.

a) I, IV

b) II, III

c) III, IV

d) I, II, IV

Q.4 Sodium salicylate can be prepared by reaction of sodium phenolate with?

a) Carbondioxide

b) Sodium hypophosphate

c) Salicylic acid

d) None of the above

Q.5 Correct sequence for the True/False for the physiochemical properties of the drug sodium salicylate is?  

I. Molecular weight = 160.1 gm/mol

II. Melting point = 100oC

III. Available in gaseous form only

IV. Ring structure present

a) FFTF

b) TFFT

c) FTTF

d) TFFF

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

I. Sodium salicylate: Sodium;2-hydroxybenzoate

II. Carmustine: 2-Chloro-N-(2-chloroethyl)-N-methylethan-1-amine

III. Lomustine: N,3-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amide 2-oxide

IV. Cisplatin: (SP-4-2)-diamminedichloroplatinum(II)

a) I, IV

b) I, II, III, IV

c) II, III

d) III, IV 

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

i. Sodium salicylate A. Inhalational anesthetics
ii. Propranolol B. ß-adrenergic blocker
iii. Promazine C. Non-selective COX inhibitor
iv. Halothane D. Phenothiazine antipsychotic drug

 a) i-B, ii-D, iii-C, iv-A

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

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

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

 

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ANSWERS

1-a

2-d

3-d

4-a

5-b

6-a

7-c

 

REFERENCES

[1] Mitchell JA, Saunders M, Barnes PJ, Newton R, Belvisi MG. Sodium salicylate inhibits cyclo-oxygenase-2 activity independently of transcription factor (nuclear factor κB) activation: role of arachidonic acid. Molecular pharmacology. 1997 Jun 1;51(6):907-12.

[2] Lemke TL, Williams DA, Roche VF, Zito SW. FOYE. S Principles of Medicinal Chemistry. Seventh Edition Copyright. 2013.

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