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Chemical Compound Review

phosphoramidon     (2S)-2-[[(2S)-2-[[hydroxy- [(3R,4R,5R,6S)-3...

Synonyms: LS-158132, AC1L236M, C23H34N3O10P, 36357-77-4, EINECS 252-996-3
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Disease relevance of phosphoramidon


Psychiatry related information on phosphoramidon


High impact information on phosphoramidon


Chemical compound and disease context of phosphoramidon


Biological context of phosphoramidon


Anatomical context of phosphoramidon


Associations of phosphoramidon with other chemical compounds

  • Leucine-thiorphan (10(-5) M) and phosphoramidon (10(-5) M) potentiated substance P-induced cough; NEP inhibitors also potentiated capsaicin-induced cough significantly [25].
  • The activity found at neutral pH values in the cytosolic fraction was only partially inhibited by EDTA and 1,10-phenanthroline but was not inhibited by phosphoramidon [22].
  • This value is in line with the concentrations obtained with [Met]enkephalin, tested in the presence of the specific neutral endopeptidase 24.11 inhibitor phosphoramidon, and this opioid's synthetic analog [D-Ala2, Met5]enkephalin which, like [D-Ala2]deltorphin I, is resistant to proteolytic degradation [26].
  • Therefore, we examined the effect of an NEP inhibitor, phosphoramidon, on myocardial perfusion in rats after (1) stimulating sensory nerves with capsaicin and (2) inducing myocardial hypoperfusion with isoproterenol, with or without pretreatment with selective antagonists of the substance P (NK1) and bradykinin (B2) receptors [27].
  • Relative to baseline values in rats with remnant kidneys, phosphoramidon led to elevations of plasma ANP levels and concomitant increases in urinary sodium excretion, fractional excretion of sodium, glomerular filtration rate, filtration fraction, and urinary cyclic GMP excretion [28].

Gene context of phosphoramidon

  • Phosphoramidon did not affect responses to endothelin-1 [18].
  • The size of the neointima was effectively reduced by phosphoramidon, an inhibitor of neutral metalloproteases, including ECE-1 [29].
  • Both ET(A) receptor antagonist [(hexahydro-1H-azepinyl)carbonyl-Leu-D-Trp-D-OH (BQ485)] and endothelin-converting enzyme inhibitor (phosphoramidon) inhibited the increased DNA synthesis caused by ET-1 [30].
  • Both agents markedly inhibited the degradation of GRP, indicating that this process involves a lysosomal pathway and a phosphoramidon-sensitive pathway, possibly involving the EC enzyme [31].
  • 7. To conclude we have demonstrated the presence of a phosphoramidon-sensitive ECE on the smooth muscle layer of the human umbilical vein which can convert big ET-1, big ET-2(1-37), big ET-2(1-38) and big ET-3 to their mature biologically active forms [32].

Analytical, diagnostic and therapeutic context of phosphoramidon


  1. Spreading and migration of human glioma and rat C6 cells on central nervous system myelin in vitro is correlated with tumor malignancy and involves a metalloproteolytic activity. Amberger, V.R., Hensel, T., Ogata, N., Schwab, M.E. Cancer Res. (1998) [Pubmed]
  2. Arrhythmogenic effects induced by coronary conversion of pulmonary big endothelin to endothelin: aggravation of this phenomenon in heritable hyperlipidemia. Alexiou, K., Dschietzig, T., Simsch, O., Laule, M., Hundertmark, J., Baumann, G., Stangl, K. J. Am. Coll. Cardiol. (1998) [Pubmed]
  3. Botulinum A like type B and tetanus toxins fulfils criteria for being a zinc-dependent protease. de Paiva, A., Ashton, A.C., Foran, P., Schiavo, G., Montecucco, C., Dolly, J.O. J. Neurochem. (1993) [Pubmed]
  4. Degradation of alpha-melanocyte stimulating hormone (alpha-MSH) by CALLA/endopeptidase 24.11 expressed by human melanoma cells in culture. Deschodt-Lanckman, M., Vanneste, Y., Loir, B., Michel, A., Libert, A., Ghanem, G., Lejeune, F. Int. J. Cancer (1990) [Pubmed]
  5. Sympathoadrenal stimulation, not endothelin, plays a role in acute pressor response to cyclosporine in anesthetized rats. Chiu, P.J., Vemulapalli, S., Sabin, C., Rivelli, M., Bernardino, V., Sybertz, E.J. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
  6. Intracellular production of beta A4 amyloid of Alzheimer's disease: modulation by phosphoramidon and lack of coupling to the secretion of the amyloid precursor protein. Fuller, S.J., Storey, E., Li, Q.X., Smith, A.I., Beyreuther, K., Masters, C.L. Biochemistry (1995) [Pubmed]
  7. An analgesic effect of enkephalinase inhibition is modulated by monoamine oxidase-B and REM sleep deprivations. Ukponmwan, O.E., Rupreht, J., Dzoljic, M. Naunyn Schmiedebergs Arch. Pharmacol. (1986) [Pubmed]
  8. Enkephalinase inhibitors attenuate naloxone-precipitated withdrawal syndrome. Dzoljic, M.R. NIDA Res. Monogr. (1986) [Pubmed]
  9. Hypertonic saline increases vascular permeability in the rat trachea by producing neurogenic inflammation. Umeno, E., McDonald, D.M., Nadel, J.A. J. Clin. Invest. (1990) [Pubmed]
  10. Common acute lymphoblastic leukemia antigen expressed on leukemia and melanoma cell lines has neutral endopeptidase activity. Jongeneel, C.V., Quackenbush, E.J., Ronco, P., Verroust, P., Carrel, S., Letarte, M. J. Clin. Invest. (1989) [Pubmed]
  11. Cigarette smoke induces bronchoconstrictor hyperresponsiveness to substance P and inactivates airway neutral endopeptidase in the guinea pig. Possible role of free radicals. Dusser, D.J., Djokic, T.D., Borson, D.B., Nadel, J.A. J. Clin. Invest. (1989) [Pubmed]
  12. Neutral endopeptidase-like enzyme controls the contractile activity of substance P in guinea pig lung. Stimler-Gerard, N.P. J. Clin. Invest. (1987) [Pubmed]
  13. Role of endothelin-1 and big endothelin-1 in modulating coronary vascular tone, contractile function and severity of ischemia in rat hearts. Grover, G.J., Sleph, P.G., Fox, M., Trippodo, N.C. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
  14. Neurogenic plasma extravasation in the rat nasal mucosa is potentiated by peptidase inhibitors. Petersson, G., Bacci, E., McDonald, D.M., Nadel, J.A. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  15. Involvement of NK2 receptors rather than NK1 receptors in bronchial hyperresponsiveness induced by allergic reaction in guinea-pigs. Mizuguchi, M., Fujimura, M., Amemiya, T., Nishi, K., Ohka, T., Matsuda, T. Br. J. Pharmacol. (1996) [Pubmed]
  16. Sch 37224, an experimental antiallergy compound, inhibits the neuropeptide component of hyperventilation- and nicotine-induced bronchoconstriction in guinea pigs. Mauser, P.J., Rasquinha, C., Hey, J.A., Kreutner, W., Egan, R.W., Sherwood, J.E., Anthes, J., Greenfeder, S., Chapman, R.W. Pharmacology (1997) [Pubmed]
  17. Endogenous methionine enkephalin may play an anticonvulsant role in the seizure-susceptible El mouse. Koide, S., Onishi, H., Katayama, M., Yamagami, S. Neurochem. Res. (1993) [Pubmed]
  18. Contribution of endogenous generation of endothelin-1 to basal vascular tone. Haynes, W.G., Webb, D.J. Lancet (1994) [Pubmed]
  19. Endothelins are more sensitive than sarafotoxins to neutral endopeptidase: possible physiological significance. Skolovsky, M., Galron, R., Kloog, Y., Bdolah, A., Indig, F.E., Blumberg, S., Fleminger, G. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  20. A peptide-hormone-inactivating endopeptidase in Xenopus laevis skin secretion. Carvalho, K.M., Joudiou, C., Boussetta, H., Leseney, A.M., Cohen, P. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  21. Protease inhibitors implicate metalloendoprotease in synaptic transmission at the mammalian neuromuscular junction. Baxter, D.A., Johnston, D., Strittmatter, W.J. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  22. The endothelin-converting enzyme from human umbilical vein is a membrane-bound metalloprotease similar to that from bovine aortic endothelial cells. Ahn, K., Beningo, K., Olds, G., Hupe, D. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  23. Substance P and [Leu]enkephalin are hydrolyzed by an enzyme in pig caudate synaptic membranes that is identical with the endopeptidase of kidney microvilli. Matsas, R., Fulcher, I.S., Kenny, A.J., Turner, A.J. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  24. Neutral endopeptidase 24.11 in human neutrophils: cleavage of chemotactic peptide. Connelly, J.C., Skidgel, R.A., Schulz, W.W., Johnson, A.R., Erdös, E.G. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  25. Neutral endopeptidase inhibitors potentiate substance P- and capsaicin-induced cough in awake guinea pigs. Kohrogi, H., Graf, P.D., Sekizawa, K., Borson, D.B., Nadel, J.A. J. Clin. Invest. (1988) [Pubmed]
  26. [D-Ala2]deltorphin I binding and pharmacological evidence for a special subtype of delta opioid receptor on human and invertebrate immune cells. Stefano, G.B., Melchiorri, P., Negri, L., Hughes, T.K., Scharrer, B. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  27. Neutral endopeptidase in the heart. Neutral endopeptidase inhibition prevents isoproterenol-induced myocardial hypoperfusion in rats by reducing bradykinin degradation. Piedimonte, G., Nadel, J.A., Long, C.S., Hoffman, J.I. Circ. Res. (1994) [Pubmed]
  28. Enkephalinase inhibition increases plasma atrial natriuretic peptide levels, glomerular filtration rate, and urinary sodium excretion in rats with reduced renal mass. Lafferty, H.M., Gunning, M., Silva, P., Zimmerman, M.B., Brenner, B.M., Anderson, S. Circ. Res. (1989) [Pubmed]
  29. Endothelin-converting enzyme expression in the rat vascular injury model and human coronary atherosclerosis. Minamino, T., Kurihara, H., Takahashi, M., Shimada, K., Maemura, K., Oda, H., Ishikawa, T., Uchiyama, T., Tanzawa, K., Yazaki, Y. Circulation (1997) [Pubmed]
  30. Crucial role of extracellular signal-regulated kinase pathway in reactive oxygen species-mediated endothelin-1 gene expression induced by endothelin-1 in rat cardiac fibroblasts. Cheng, C.M., Hong, H.J., Liu, J.C., Shih, N.L., Juan, S.H., Loh, S.H., Chan, P., Chen, J.J., Cheng, T.H. Mol. Pharmacol. (2003) [Pubmed]
  31. Characterization of ligand binding and processing by gastrin-releasing peptide receptors in a small-cell lung cancer cell line. Cardona, C., Bleehen, N.M., Reeve, J.G. Biochem. J. (1992) [Pubmed]
  32. Endothelin converting enzyme (ECE) activity in human vascular smooth muscle. Maguire, J.J., Johnson, C.M., Mockridge, J.W., Davenport, A.P. Br. J. Pharmacol. (1997) [Pubmed]
  33. Endothelin B receptor antagonists attenuate subarachnoid hemorrhage-induced cerebral vasospasm. Zuccarello, M., Boccaletti, R., Romano, A., Rapoport, R.M. Stroke (1998) [Pubmed]
  34. Phosphoramidon modulates the number of endothelin receptors in cultured Swiss 3T3 fibroblasts. Wu-Wong, J.R., Chiou, W.J., Opgenorth, T.J. Mol. Pharmacol. (1993) [Pubmed]
  35. Inhibition of endothelin-converting enzyme attenuates transplant vasculopathy and rejection in rat cardiac allografts. Simonson, M.S., Herman, W.H., Robinson, A., Schulak, J., Hricik, D.E. Transplantation (1999) [Pubmed]
  36. Recombinant human endothelin-converting enzyme ECE-1b is located in an intracellular compartment when expressed in polarized Madin-Darby canine kidney cells. Azarani, A., Boileau, G., Crine, P. Biochem. J. (1998) [Pubmed]
  37. Effect of an inhaled neutral endopeptidase inhibitor, phosphoramidon, on baseline airway calibre and bronchial responsiveness to bradykinin in asthma. Crimi, N., Polosa, R., Pulvirenti, G., Magrì, S., Santonocito, G., Prosperini, G., Mastruzzo, C., Mistretta, A. Thorax (1995) [Pubmed]
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