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Synthesis of Acetazolamide

Reaction Summary Starting reaction occurs in-between hydrazine hydrate and ammonium thiocyanate that produces 1, 2-bis (thiocar...




Reaction Summary
Starting reaction occurs in-between hydrazine hydrate and ammonium thiocyanate that produces 1, 2-bis (thiocarbamoyl) hydrazine which on further treatment with phosgene undergoes rearrangements, particularly  molecular rearrangement through loss of ammonia to form 5-amino-2-mercapto-1, 3, 4-thiadiazole. Upon acylation of 5-amino-2-mercapto-1, 3, 4-thiadiazole gives a corresponding amide which on oxidation with aqueous chlorine affords the 2-sulphonyl chloride. The final step essentially consists of amidation by treatment with ammonia.


Brief Pharmacology


  • Acetazolamide is prtotype in carbonic anhydrase inhibitors, 
  • Acetzolamide act at the proximal tubule, where carbonic anhydrase is membrane-bound and normally catalyses H2CO3-> H2O + CO2 in the lumen and the reverse reaction in the cytoplasm. By blocking CA, acetazolamide inhibit NaHCO3 reabsorption in the proximal tubule.
  • Used to treat 
  1. glaucoma, 
  2. drug-induced edema, 
  3. heart failure-induced edema, 
  4. centrencephalic epilepsy 
  5. and in reducing intraocular pressure after surgery.