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

Gold Sodium Thiomalate

Or

Sodium Aurothiomalate

IUPAC nomenclature

Disodium;gold(1+);2-sulfidobutanedioate;hydrate

Classification

  • Synthetic Disease-Modifying Ant rheumatic Drugs (DMARDs)
  • Gold compounds

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 408.09 g/mol
2 Physical appearance Mixture of mono- and disodium salts; white to yellowish-white powder
3 Melting point 100oC
4 Solubility Very soluble in water and insoluble in alcohol
5 Octanol/water partition coefficient N/A
6 Presence of ring Not present
7 Number of chiral centers Not present

 

Mechanism of Action

  • Gold sodium thiomalate inhibits prostaglandins synthesis
  • There is a suppressive effect on the synovitis of active rheumatoid disease by the drug.

 

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. Thiomalic acid is mixed with the aqueous suspension of gold(I)iodide.

ii. The resultant mono- and disodium salts are precipitated by the addition of ethanol.[2]

Therapeutic Uses

Gold sodium thiomalate is used for:

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

 

Side Effects

Side effects of Gold sodium thiomalate are:

  • Dizziness
  • Drowsiness
  • Flushing
  • Headache
  • Vomiting
  • Weakness
  • Sweating
  • Eye pain
  • Eye redness
  • Fainting
  • Loss of hair
  • Mood changes
  • Confusion
  • Hallucinations
  • Seizures
  • Stomatitis
  • Painful breathing
  • Low blood count signs
  • Pale skin color
  • Cough
  • Diarrhea
  • Grayish or bluish skin color
  • Abdominal pain
  • Urine color changes
  • Vaginal sores
  • Allergic reactions
  • Rash

 

 

MCQs

Q.1 Which statements are correct with respect to the physicochemical properties of drug gold sodium thiomalate?

I. Molecular weight:408.09gm/mol

II. Appearance: Yellow white crystalline solid

III. Melting point: 153oC

a) I, II

b) II, III

c) I, II, III

d) I, III

Q.2 Match the following of the drugs with their correct IUPAC names.

i. Gold sodium thiomalate A. ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate
ii. Diclofenac B. (5α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
iii. Diphenoxylate C. Disodium;gold(1+);2-sulfidobutanedioate;hydrate
iv. Codeine     D. [2-(2,6-Dichloroanilino)phenyl]acetic acid

 a) i-C, ii-D, iii-A, iv-B

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

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

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

Q.3 Mechanism of action of Gold sodium thiomalate includes?

I. Inhibition of prostaglandin synthesis

II. Inhibition of acetylcholine synthesis

III. Suppressive effect on synovitis of active rheumatoid disease

IV. Alkylation of genetic material

a) II, IV

b) I, II, III

c) I, III

d) II, III, IV

Q.4 Correct sequence for True/false for the classification of the drug can be?

  • Gold sodium thiomalate: DMARDs
  • Prednisolone: Antineoplastic drugs
  • Anastrozole: NSAID
  • CCNU: Triazine alkylating agent

a) TFFT

b) FTFT

c) FFTF

d) TTFF

Q.5 In the gold compound DMARDs, attachment of the gold with sulfur?

a) Decreases the activity

b) Increases the activity

c) Is essential for the activity

d) Has no impact on the activity of drug

Q.6 Type of ring present in the structure of Sodium aurothiomalate?

I. Oxazolidine

II. Naphthaline

III. Phenyl

IV. Furan

a) I, III

b) II, IV

c) I, III, IV

d) No ring structure present 

Q.7 Side effect of drug Gold sodium thiomalate?

a) Seizures

b) Eye redness

c) Stomatitis

d) All of the above

 

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ANSWERS

1-a

2-a

3-c

4-d

5-c

6-d

7-d

 

REFERENCES

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

[2] Ullmann’s Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V3 540(2003)

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