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

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

  1. Auranofin

IUPAC nomenclature

gold(1+);3,4,5-triacetyloxy-6-(acetyloxymethyl)oxane-2-thiolate;triethylphosphanium

Classification

  • Synthetic Disease-Modifying Antirheumatic Drugs (DMARDs)
  • Gold compounds

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 679.5 g/mol
2 Physical appearance White crystalline powder
3 Melting point 112-115oC
4 Solubility Insoluble in water
5 Octanol/water partition coefficient N/A
6 Presence of ring Pyran
7 Number of chiral centers 5

 

Mechanism of Action

  • Auranofin inhibits the immune response by inhibiting kappab kinase and thioredoxin reductase enzymes.
  • Decreases in the immune response decreases inflammation at the joint lining in the patients suffering from arthritis.

Structure Activity Relationship

General SAR for Gold compounds can be summarized as follows:

  • Monovalent gold is more active than trivalent or colloidal gold.
  • Attachment of the gold with the sulfur containing ligand is essential for the activity of the drug.
  • Complexation of the gold ions with phosphine increases the bioavailability.
  • Injectible gold compounds should be monocoordinated.
  • Triethylphosphine gold compounds show the highest activity. [1]

 

Method of synthesis

i. Reaction of thioether with silver nitrate or any other heavy metal salt to give silver salt of sugar thiol.

ii. On reacting the last with tert-phosphine gold reagent produces auranofin.[2]

Therapeutic Uses

Auranofin is used for:

  • Treatment of patients having rheumatoid arthritis that did not respond to or cannot take other medication for the disease. 

 

Side Effects

Side effects of Auranofin are:

  • Abdominal cramping
  • Nausea
  • Loss of appetite
  • Headache
  • Heartburn
  • Eye pain
  • Eye redness
  • Loss of hair
  • Numbness
  • Tingling in arms
  • Stomatitis
  • Pale skin
  • Tiredness
  • Easy bleeding
  • Diarrhea
  • Painful breathing
  • Allergic reactions
  • Skin rash
  • Itching 

 

MCQs

Q.1 “gold(1+);3,4,5-triacetyloxy-6-(acetyloxymethyl)oxane-2-thiolate;triethylphosphanium” is the IUPAC nomenclature of which drug?

a) Gold sodium thiomalate

b) Aurothioglucose

c) Auranofin

d) Oxymetazoline

Q.2 Appearance of auranofin is?

a) White crystalline solid

b) Yellow powder

c) Black amorphous solid

d) None of the above

Q.3 Match the following with correct classifications of the drugs.

i. Auranofin A. Non-selective adrenergic agonist
ii. Norepinephrin B. Cholinestrase reactivator
iii. Pralidoxime C. ß-blocker
iv. Carvedilol D. DMARDs

 a) i-A, ii-D, iii-B, iv-C

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

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

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

Q.4 Correct statements from below which are related with the mechanism of action of Auranofin can be??

I. It inhibits thioredoxin reductase enzyme

II. It activates thioridoxin reducatse enzyme

III. It decreases the immune response

IV. It increases the immune response

a) I, III

b) I, IV

c) II, III

d) II, IV

Q.5   Correct sequence for True and False for the given statements related with the SAR of Anti-inflammatory gold compounds can be?

  • Monovalent gold is less active than trivalent or colloidal gold.
  • Attachment of the gold with the sulfur containing ligand is essential for the activity of the drug.
  • Complexation of the gold ions with phosphine decreases the bioavailability.
  • Injectible gold compounds should be monocoordinated

a) TFFT

b) FFTT

c) FTFT

d) TTTT

Q.6  Silver salt of sugar thiol can produce Auranofin by reaction with?

a) Baeyer’s reagent

b) Silver nitrate

c) Tert-phosphine gold reagent

d) Lead acetate 

Q.7 The drug Auranofin is mainly used for?

a) Treatment of Parkinson disease

b) For reversing the toxicity due to cholinergic drugs

c) Reducing pain due to arthritis

d) All of the above

 

 

 

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ANSWERS

1-c

2-a

3-b

4-a

5-c

6-c

7-c

 

REFERENCES

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

[2] Hill DT, Lantos I, Sutton BM, inventors; SmithKline Corp, assignee. Process for preparing auranofin. United States patent US 4,122,254. 1978 Oct 24.

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