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Chemical Compound Review

Iprazid     N'-propan-2-ylpyridine-4- carbohydrazide

Synonyms: Euphozid, Marsalid, Marsilid, Ipronid, Iprozid, ...
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Disease relevance of iproniazid

  • The effect of the mixed-function oxidase inhibitor phenylimidazole (PI) and the amine oxidase inhibitors iproniazid (IPRO) and aminoacetonitrile (AAN) on the mutagenic activity of various carcinogens was determined in intrasanguineous host-mediated assays, using mice as hosts and E. coli 343/113 as an indicator of mutagenic activity [1].
  • As MAO is irreversibly inhibited by iproniazid, these results suggest that the mechanism of iproniazid-induced appearance of anti-M6 antibodies could be another example of the reactive metabolite/enzyme haptenization mechanism already proposed in the case of tienilic acid for the appearance of anti-organelle antibodies in a drug-induced hepatitis [2].
  • The modification of pethidine analgesia and hypothermia, but not morphine analgesia, was antagonized by methysergide (10 mg lg-1, s.c.). The LD50 of pethidine, but not that of morphine, was 30-40% lower in mice treated with phenelzine tranylcypromine or iproniazid 6 h before the test [3].
  • Effect of postnatal anoxia on seizure susceptibility in rats: bicuculline-induced seizures and pretreatment with iproniazid [4].
  • These results support an indirect sympathomimetic action of MF and raise the question whether commonly used antidepressants with properties similar to iproniazid and desipramine might alter MF's beneficial vasodilatory (and thus antihypertensive) effectiveness in diabetic patients with hypertension [5].

Psychiatry related information on iproniazid

  • The modern era of psychopharmacology of mood disorders began in the late 1940s with John Cade's discovery of the mood-stabilizing properties of lithium.1 Less than 5 years later came the unexpected observation of elevated mood and activation among patients on a tuberculosis ward who were treated with the antitubercular agent, iproniazid [6].

High impact information on iproniazid


Biological context of iproniazid


Anatomical context of iproniazid


Associations of iproniazid with other chemical compounds


Gene context of iproniazid

  • Human anti-mitochondria autoantibodies appearing in iproniazid-induced immunoallergic hepatitis recognize human liver monoamine oxidase B [2].
  • Iproniazid (Ipr) is a typical monoamine oxidase (MAO) inhibitor which as well seems capable of inhibiting to a certain extent P-450 mediated metabolism [13].
  • However, in HL60 cells, procarbazine was metabolized by myeloperoxidase while iproniazid was metabolized mostly by the cytochrome P-450 system [26].
  • The strong effect of iproniazid is probably due to its DAO inhibiting properties [27].
  • Importantly, iproniazid, the nonselective MAO inhibitor, caused changes in PBR binding in all three of the tissues [28].

Analytical, diagnostic and therapeutic context of iproniazid

  • The resulting mixtures were stirred for 20 hours (96 hours for iproniazid) and analyzed by high-performance liquid chromatography and gas chromatography for the presence of residual drug and degradation products [29].
  • Subsequent clinical trials led to the widespread, but short-lived, use of iproniazid for treatment of depression in 1957 and demonstration of its monoamine oxidase inhibitor properties [6].


  1. The effect of mixed-function oxidase and amine oxidase inhibitors on the activation of dialkylnitrosamines and 1,2-dimethylhydrazine to bacterial mutagens in mice. Kerklaan, P.R., Bouter, S., Zijlstra, J.A., Mohn, G.R. J. Cancer Res. Clin. Oncol. (1986) [Pubmed]
  2. Human anti-mitochondria autoantibodies appearing in iproniazid-induced immunoallergic hepatitis recognize human liver monoamine oxidase B. Pons, C., Dansette, P.M., Gregeois, J., Homberg, J.C., Billett, E.E., Mansuy, D. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  3. Modification by monoamine oxidase inhibitors of the analgesic, hypothermic and toxic actions of morphine and pethidine in mice. Botting, R., Bower, S., Eason, C.T., Hutson, P.H., Wells, L. J. Pharm. Pharmacol. (1978) [Pubmed]
  4. Effect of postnatal anoxia on seizure susceptibility in rats: bicuculline-induced seizures and pretreatment with iproniazid. Mutoh, F. Life Sci. (1991) [Pubmed]
  5. A possible indirect sympathomimetic action of metformin in the arterial vessel wall of spontanously hypertensive rats. Lee, J.M., Peuler, J.D. Life Sci. (2001) [Pubmed]
  6. Advancing the treatment of mood and anxiety disorders: the first 10 years' experience with paroxetine. Nemeroff, C.B. Psychopharmacology bulletin. (2003) [Pubmed]
  7. Drugs that induce systemic lupus erythematosus inhibit complement component C4. Sim, E., Gill, E.W., Sim, R.B. Lancet (1984) [Pubmed]
  8. Iproclozide fulminant hepatitis. Possible role of enzyme induction. Pessayre, D., de Saint-Louvent, P., Degott, C., Bernuau, J., Rueff, B., Benhamou, J.P. Gastroenterology (1978) [Pubmed]
  9. Spin trapping of free radical intermediates produced during the metabolism of isoniazid and iproniazid in isolated hepatocytes. Albano, E., Tomasi, A. Biochem. Pharmacol. (1987) [Pubmed]
  10. Influence of thyroid status on responses of rat isolated pulmonary artery, vas deferens and trachea to smooth muscle relaxant drugs. O'Donnell, S.R., Wanstall, J.C., Mustafa, M.B. Br. J. Pharmacol. (1987) [Pubmed]
  11. The effect of monoamine oxidase and catechol O-methyltransferase inhibitors on the accumulation and metabolism of [l-3H] norepinephrine by the adventitia and media of rabbit aorta. Levin, J.A., Wilson, S.E. J. Pharmacol. Exp. Ther. (1977) [Pubmed]
  12. The role of biotransformation in chemical-induced liver injury. Mitchell, J.R., Snodgrass, W.R., Gillette, J.R. Environ. Health Perspect. (1976) [Pubmed]
  13. Influence of inhibition of the metabolic activation on the mutagenicity of some nitrosamines, triazenes, hydrazines and seniciphylline in Drosophila melanogaster. Zijlstra, J.A., Vogel, E.W. Mutat. Res. (1988) [Pubmed]
  14. Propane and propylene formation during the microsomal metabolism of iproniazid and isopropylhydrazine. Moloney, S.J., Guengerich, F.P., Prough, R.A. Life Sci. (1985) [Pubmed]
  15. Genotoxic activity of five antidepressant hydrazines in a battery of in vivo and in vitro short-term tests. Brambilla, G., Cavanna, M., Faggin, P., Pino, A., Robbiano, L., Bennicelli, C., Zanacchi, P., Camoirano, A., De Flora, S. Journal of toxicology and environmental health. (1982) [Pubmed]
  16. An electrophysiological analysis of the effects of reserpine on adrenergic neuromuscular transmission. Bennett, M.R., Middleton, J. Br. J. Pharmacol. (1975) [Pubmed]
  17. Effect of some monoamine oxidase inhibitors on the thiamin status of rabbits. Ali, B.H. Br. J. Pharmacol. (1985) [Pubmed]
  18. Influence of metabolic factors on the mutagenic effectiveness of cyclophosphamide in Drosophila melanogaster. Zijlstra, J.A., Vogel, E.W. Mutat. Res. (1989) [Pubmed]
  19. The effects of reserpine, iproniazid and L-dopa on electrically-induced spinal cord seizures. Jobe, P.C., Ray, T.B. Res. Commun. Chem. Pathol. Pharmacol. (1980) [Pubmed]
  20. Examination of the paradoxical lack of responsiveness of the guinea-pig vas deferens to tyramine. Rand, M.J., Story, D.F., Dowding, T. Journal of autonomic pharmacology. (1989) [Pubmed]
  21. Carbon-11 labeled aliphatic amines in lung uptake and metabolism studies: potential for dynamic measurements in vivo. Fowler, J.S., Gallagher, B.M., MacGregor, R.R., Wolf, A.P. J. Pharmacol. Exp. Ther. (1976) [Pubmed]
  22. Hepatotoxicity and metabolism of iproniazid and isopropylhydrazine. Nelson, S.D., Mitchell, J.R., Snodgrass, W.R., Timbrell, J.A. J. Pharmacol. Exp. Ther. (1978) [Pubmed]
  23. Inactivation of neural and exogenous norepinephrine in rat tail artery studied by the oil immersion technique. Wyse, D.G. J. Pharmacol. Exp. Ther. (1976) [Pubmed]
  24. Properties of the depolarization induced by TRH in the isolated frog spinal cord. Oka, J., Fukuda, H. Neurosci. Lett. (1984) [Pubmed]
  25. Behavioral withdrawal following several psychoactive drugs. Simpson, D.M., Annau, Z. Pharmacol. Biochem. Behav. (1977) [Pubmed]
  26. Cytochrome P-450- and peroxidase-dependent activation of procarbazine and iproniazid in mammalian cells. Sinha, B.K. Free Radic. Res. Commun. (1991) [Pubmed]
  27. Monoamine oxidase inhibitors and histamine metabolism. Benedetti, M.S., Ancher, J.F., Sontag, N. Experientia (1980) [Pubmed]
  28. Selective effects of MAO inhibition on peripheral benzodiazepine receptor binding in the mouse. Park, C.H., Lukacs, L.G., Mastropaolo, J., Deutsch, S.I. The Israel journal of psychiatry and related sciences. (1997) [Pubmed]
  29. Reductive destruction of dacarbazine, procarbazine hydrochloride, isoniazid, and iproniazid. Lunn, G., Sansone, E.B. American journal of hospital pharmacy. (1987) [Pubmed]
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