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Minaprine

Chemical compound

Chemical compound

| Drugs.com = | elimination_half-life = 2-2.5 hours

Minaprine (INN, USAN, BAN; brand names Brantur, Cantor) is a monoamine oxidase inhibitor antidepressant drug that was used in France for the treatment of depression until it was withdrawn from the market in 1996 because it caused convulsions.

A study found that it acts as a reversible inhibitor of MAO-A (RIMA) in rats. It has also been found to weakly inhibit acetylcholinesterase in rat brain (striatum) homogenates.

It has demonstrated significant antibiotic activity against M. chelonae and M. abscessus in tests with antibiotic resistant bacteria.

Synthesis

The first synthesis of minaprine was disclosed in patents published in 1979. :[[File:Minaprine synthesis 1989.svg|class=skin-invert-image|upright=2]] The final step is the reaction between a chloro-substituted pyridazine and the primary amine group of a morpholine derivative. The required pyridazine can be made by the reaction of acetophenone and pyruvic acid, followed by ring formation using hydrazine, giving a pyrazidinone. Treatment of this with phosphoryl chloride converts it to the required chloro derivative.

References

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. (March 1989). "3-aminopyridazine derivatives with atypical antidepressant, serotonergic, and dopaminergic activities". Journal of Medicinal Chemistry.
  3. (1 January 2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Therapeutic Innovation & Regulatory Science.
  4. (March 1986). "Effect of the antidepressant minaprine on both forms of monoamine oxidase in the rat". Biochemical Pharmacology.
  5. (February 1999). "Aminopyridazines as acetylcholinesterase inhibitors". Journal of Medicinal Chemistry.
  6. (July 2011). "Identification of antimicrobial activity among FDA-approved drugs for combating Mycobacterium abscessus and Mycobacterium chelonae". The Journal of Antimicrobial Chemotherapy.
  7. "Pyridazine derivatives in alleviating depressive states".
  8. "Minaprine". Thieme.
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acetylcholinesterase-inhibitors antidepressants aromatic-amines monoamine-oxidase-inhibitors 4-morpholinyl-compounds pyridazines
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