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Chemical Compound Review

Zoprace     (2S,4S)-1-[(2R)-2-methyl-3...

Synonyms: Zofenopril, Zofenoprilum, TPC-I147, Zofenil (TN), CHEMBL331378, ...
 
 
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Disease relevance of Zofenopril

 

Psychiatry related information on Zofenopril

  • In conclusion, zofenopril/HCTZ 30/12.5 mg/day provides more optimal BP control in a larger proportion of patients than would be achievable with monotherapy, while maintaining the tolerability profile observed with each individual agent, and thereby potentially enhancing patient compliance [3].
  • Conversely the prevalence of severe CHF (1.6% vs 2.6%: risk reduction 55.5%; 95% confidence interval 9 to 63; p = 0.0325) and the combined occurrence of death or severe CHF (4.8% vs 8.2%: risk reduction 59%; 95% confidence interval 11 to 71; p = 0.024) were reduced after 6 weeks of treatment with zofenopril [6].
 

High impact information on Zofenopril

 

Chemical compound and disease context of Zofenopril

  • CONCLUSIONS: In rats with renovascular hypertension and hypertensive heart disease that included LVH and fibrosis, equipotent doses of ZOF, NIF, and LAB normalized arterial pressure associated with regression of LVH while only ZOF and NIF were found to regress myocardial fibrosis [10].
  • Neither zofenopril nor captopril, however, had any effect on coronary flow before or after ischemia [11].
  • These data suggest that the cardioprotective effect of zofenopril and captopril is independent of hemodynamic changes or reduction of the toxicity of oxygen free radicals and that it could be related to a reduction in release of NE [12].
  • CONCLUSIONS: The SMILE-2 study demonstrates that both zofenopril and lisinopril are safe and associated with a rather low rate of severe hypotension when given in accordance with a dose-titrated scheme to thrombolyzed patients with acute MI [13].
 

Biological context of Zofenopril

  • Systemic blood pressure was acutely reduced by zofenopril, and severe but reversible hypotension occurred in 15% of hospitalized patients and in 3% of those treated over the long term [14].
  • Left ventricular size decreased and ejection fraction (EF) increased in patients who received zofenopril, and the improvement was greater among patients with poorer ventricular function (EF less than 40%) [14].
  • Extraction ratios (E) for zofenopril by the gut, liver, and lungs were calculated based on the ratios of the area under the curve (AUC) values of zofenopril in arterial plasma after administration by the various routes [15].
  • Fosinopril and zofenopril had the greatest inhibitory potency (IC50 values of 55 and 81 microM, respectively) while the other ACE inhibitors exhibited low-affinity interactions with the renal peptide transporter [16].
  • Two hours after oral administration of 7.5 mg of zofenopril we observed a decrease in blood pressure, heart rate, and forearm vascular resistance along with an increase in venous distensibility [17].
 

Anatomical context of Zofenopril

  • The SH-containing angiotensin-converting enzyme (ACE) inhibitors zofenopril and captopril have been shown to protect the ischemic myocardium independently of ACE inhibition [18].
  • Zofenopril has been reported to cause relaxation in aortic smooth muscle rings via an endothelium-dependent component [18].
  • Zofenopril inhibits the expression of adhesion molecules on endothelial cells by reducing reactive oxygen species [19].
  • Compared to zofenopril-treated rabbits, arterial sections of the placebo-group had significant increase in the intimal presence of macrophages-derived foam cells (p < 0.05), ox-LDL (p < 0.01), and native LDL (p < 0.01) detected by immunocytochemistry with RAM-11, MDA2 and NP1533975 monoclonal antibodies, respectively [20].
  • In the placebo-treated group, platelet radioactivity was 0.52+/-0.12 equivalent of radioactivity per mg of tissue in the common carotid and 0.25+/-0.18 in the abdominal aorta; in contrast, rabbits treated by zofenopril had 0.20+/-0.12 in the common carotid and 0.06+/-0.01 in the abdominal aorta [20].
 

Associations of Zofenopril with other chemical compounds

  • The haemodynamic effects of the sulfhydryl-containing angiotensin converting enzyme inhibitor, zofenopril, were studied in patients in New York Heart Association functional class II and III [9].
  • In clinical trials comparing zofenopril/HCTZ with each agent administered as monotherapy, combination therapy was more effective in normalising BP [3].
  • Zofenoprilat, the active form of zofenopril, significantly and dose dependently reduced the intracellular reactive oxygen species (ROS) and superoxide formation induced by oxidized low-density lipoprotein (ox-LDL) (P <.001) and tumor necrosis factor-alpha (TNF-alpha) (P <.001) [19].
  • Atenolol reduced blood pressure (BP) by 0 +/- 6/8 +/- 2 mm Hg (ns/P < 0.01), and zofenopril by 14 +/- 4/6 +/- 2 (P < 0.01/P < 0.01), not significantly different between the two agents [21].
  • The effects of chronic treatment with the new sulfhydryl angiotensin-converting enzyme (ACE)-inhibitor, zofenopril, in comparison with the classical sulfhydryl ACE-inhibitor captopril or enalapril or placebo on the development of atherosclerosis were determined in apolipoprotein-E knockout (apoE(-/-)) mice [22].
 

Gene context of Zofenopril

  • The lipid peroxidation, protein oxidation, and nitric oxide levels as well as xanthine oxidase and myeloperoxidase activities were increased and the catalase and superoxide dismutase activities were decreased in the IR group; zofenopril treatment prevented these changes (p <0.05) [23].
  • The cardioprotective activity of 100 microM zofenopril was abolished by both KATP blockers [18].
  • We conclude that oral acute zofenopril administration, in patients with congestive heart failure, causes an arterial and venous forearm vasodilatation which is probably involved in the acute changes in plasma levels of ANF and AVP observed after drug administration [17].
  • The aim of the present study was to evaluate the importance of a history of HBP on the clinical efficacy of early treatment with the angiotensin-converting enzyme (ACE) inhibitor zofenopril in patients with anterior AMI [24].
  • Zofenopril administration was followed by a dose-dependent inhibition of in vitro ACE activity (7.5 mg, 65%; 15 mg, 89%; 30 mg, 94.5%) and a progressive increase in plasma active renin [25].
 

Analytical, diagnostic and therapeutic context of Zofenopril

References

  1. Zofenopril after anterior myocardial infarction. Mörike, K., Mikus, G. N. Engl. J. Med. (1995) [Pubmed]
  2. Equipotent antihypertensive agents variously affect pulsatile hemodynamics and regression of cardiac hypertrophy in spontaneously hypertensive rats. Mitchell, G.F., Pfeffer, M.A., Finn, P.V., Pfeffer, J.M. Circulation (1996) [Pubmed]
  3. Zofenopril plus hydrochlorothiazide: Combination therapy for the treatment of mild to moderate hypertension. Zanchetti, A., Parati, G., Malacco, E. Drugs (2006) [Pubmed]
  4. Converting enzyme inhibition after experimental myocardial infarction in rats: comparative study between spirapril and zofenopril. van Wijngaarden, J., Pinto, Y.M., van Gilst, W.H., de Graeff, P.A., de Langen, C.D., Wesseling, H. Cardiovasc. Res. (1991) [Pubmed]
  5. Clinical pharmacology of the ACE inhibitors. Fyhrquist, F. Drugs (1986) [Pubmed]
  6. Effects of the early administration of zofenopril on onset and progression of congestive heart failure in patients with anterior wall acute myocardial infarction. The SMILE Study Investigators. Survival of Myocardial Infarction Long-term Evaluation. Borghi, C., Ambrosioni, E., Magnani, B. Am. J. Cardiol. (1996) [Pubmed]
  7. The effect of the angiotensin-converting-enzyme inhibitor zofenopril on mortality and morbidity after anterior myocardial infarction. The Survival of Myocardial Infarction Long-Term Evaluation (SMILE) Study Investigators. Ambrosioni, E., Borghi, C., Magnani, B. N. Engl. J. Med. (1995) [Pubmed]
  8. Sustained augmentation of parasympathetic tone with angiotensin-converting enzyme inhibition in patients with congestive heart failure. Binkley, P.F., Haas, G.J., Starling, R.C., Nunziata, E., Hatton, P.A., Leier, C.V., Cody, R.J. J. Am. Coll. Cardiol. (1993) [Pubmed]
  9. Angiotensin converting enzyme inhibition at rest and during exercise in congestive heart failure. Kelbaek, H., Agner, E., Wroblewski, H., Vasehus Madsen, P., Marving, J. Eur. Heart J. (1993) [Pubmed]
  10. Regression of myocardial fibrosis in hypertensive heart disease: diverse effects of various antihypertensive drugs. Brilla, C.G. Cardiovasc. Res. (2000) [Pubmed]
  11. Effects of different angiotensin-converting enzyme (ACE) inhibitors on ischemic isolated rat hearts: relationship between cardiac ACE inhibition and cardioprotection. Grover, G.J., Sleph, P.G., Dzwonczyk, S., Wang, P., Fung, W., Tobias, D., Cushman, D.W. J. Pharmacol. Exp. Ther. (1991) [Pubmed]
  12. Protection of the ischemic myocardium by the converting-enzyme inhibitor zofenopril: insight into its mechanism of action. Ferrari, R., Cargnoni, A., Curello, S., Ceconi, C., Boraso, A., Visioli, O. J. Cardiovasc. Pharmacol. (1992) [Pubmed]
  13. Double-blind comparison between zofenopril and lisinopril in patients with acute myocardial infarction: results of the Survival of Myocardial Infarction Long-term Evaluation-2 (SMILE-2) study. Borghi, C., Ambrosioni, E. Am. Heart J. (2003) [Pubmed]
  14. Early treatment of acute myocardial infarction with angiotensin-converting enzyme inhibition: safety considerations. SMILE pilot study working party. Ambrosioni, E., Borghi, C., Magnani, B. Am. J. Cardiol. (1991) [Pubmed]
  15. Sites of first-pass bioactivation (hydrolysis) of orally administered zofenopril calcium in dogs. Morrison, R.A., Burkett, D.E., Arnold, M.E., D'Arienzo, C.J., Weinstein, S.H. Pharm. Res. (1991) [Pubmed]
  16. Competitive inhibition of glycylsarcosine transport by enalapril in rabbit renal brush border membrane vesicles: interaction of ACE inhibitors with high-affinity H+/peptide symporter. Lin, C.J., Akarawut, W., Smith, D.E. Pharm. Res. (1999) [Pubmed]
  17. Peripheral hemodynamic and humoral effects of oral zofenopril calcium (SQ. 26,991) in patients with congestive heart failure. Borghi, C., Magelli, C., Boschi, S., Costa, F.V., Capelli, M., Varani, E., Magnani, B., Ambrosioni, E. Journal of clinical pharmacology. (1989) [Pubmed]
  18. Cardioprotection in ischemic rat hearts with the SH-containing angiotensin-converting enzyme inhibitor zofenopril: possible involvement of the ATP-sensitive potassium channel. Sargent, C.A., Sleph, P.G., Dzwonczyk, S., Smith, M.A., Normandin, D., Antonaccio, M.J., Grover, G.J. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  19. Zofenopril inhibits the expression of adhesion molecules on endothelial cells by reducing reactive oxygen species. Cominacini, L., Pasini, A., Garbin, U., Evangelista, S., Crea, A.E., Tagliacozzi, D., Nava, C., Davoli, A., LoCascio, V. Am. J. Hypertens. (2002) [Pubmed]
  20. Beneficial effects of ACE-inhibition with zofenopril on plaque formation and low-density lipoprotein oxidation in watanabe heritable hyperlipidemic rabbits. Napoli, C., Cicala, C., D'Armiento, F.P., Roviezzo, F., Somma, P., de Nigris, F., Zuliani, P., Bucci, M., Aleotti, L., Casini, A., Franconi, F., Cirino, G. Gen. Pharmacol. (1999) [Pubmed]
  21. The effects of atenolol and zofenopril on plasma atrial natriuretic peptide are due to their interactions with target organ damage of essential hypertensive patients. Elijovich, F., Laffer, C.L., Schiffrin, E.L. Journal of human hypertension. (1997) [Pubmed]
  22. Chronic treatment with sulfhydryl angiotensin-converting enzyme inhibitors reduce susceptibility of plasma LDL to in vitro oxidation, formation of oxidation-specific epitopes in the arterial wall, and atherogenesis in apolipoprotein E knockout mice. de Nigris, F., D'Armiento, F.P., Somma, P., Casini, A., Andreini, I., Sarlo, F., Mansueto, G., De Rosa, G., Bonaduce, D., Condorelli, M., Napoli, C. International journal of cardiology. (2001) [Pubmed]
  23. An Angiotensin-converting enzyme inhibitor, zofenopril, prevents renal ischemia/reperfusion injury in rats. Altunoluk, B., Soylemez, H., Oguz, F., Turkmen, E., Fadillioglu, E. Ann. Clin. Lab. Sci. (2006) [Pubmed]
  24. Effects of the administration of an angiotensin-converting enzyme inhibitor during the acute phase of myocardial infarction in patients with arterial hypertension. SMILE Study Investigators. Survival of Myocardial Infarction Long-term Evaluation. Borghi, C., Bacchelli, S., Esposti, D.D., Bignamini, A., Magnani, B., Ambrosioni, E. Am. J. Hypertens. (1999) [Pubmed]
  25. Evidence of a partial escape of renin-angiotensin-aldosterone blockade in patients with acute myocardial infarction treated with ACE inhibitors. Borghi, C., Boschi, S., Ambrosioni, E., Melandri, G., Branzi, A., Magnani, B. Journal of clinical pharmacology. (1993) [Pubmed]
  26. The role of zofenopril in myocardial protection during cardioplegia arrest: an isolated rat heart model. Leva, C., Mariscalco, G., Ferrarese, S., Bruno, V.D., Orrù, A., Cattaneo, P., Sala, A. Journal of cardiac surgery. (2006) [Pubmed]
  27. Assay of zofenopril and its active metabolite zofenoprilat by liquid chromatography coupled with tandem mass spectrometry. Dal Bo, L., Mazzucchelli, P., Marzo, A. J. Chromatogr. B Biomed. Sci. Appl. (2000) [Pubmed]
 
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