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Chemical Compound Review

Retrothiorphan     2-[(1-phenyl-3-sulfanyl- propan-2...

Synonyms: CHEMBL38405, AR-1F4794, AC1L33I3, AC1Q5V7I, 82154-09-4, ...
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High impact information on Retrothiorphan

  • This hypothesis is supported by reported crystallographic studies on related enzymes such as thermolysin and carboxypeptidase A. As expected, retro-thiorphan exhibits about the same analgesic potency as thiorphan on the hot plate and writhing tests in mice [1].
  • Inhibition of neutral endopeptidase with retrothiorphan (25 nM) had no effect on BK degradation [2].
  • Thiorphan [N-[(S)-2-(mercaptomethyl)-1-oxo-3-phenylpropyl]glycine] [HSCH2CH(CH2C6H5)CONHC-H2COOH] and retro-thiorphan [[[(R)-1-(mercaptomethyl)-2-phenylethyl] amino]-3-oxopropanoic acid] [HSCH2CH(CH2C6H5)NHCOCH2COOH] are isomeric thiol-containing inhibitors of endopeptidase EC 24-11 (also called "enkephalinase") [3].
  • At a lower dose (10 micrograms kg-2), ANP alone or with retrothiorphan or the C-ANP receptor ligand C-ANP (4-23) did not produce any arteriolar responses, while after the combined administration of the two inhibitors, an increase in arteriolar diameter was induced [4].
  • Renal clearance studies in DOCA-salt rats showed that retrothiorphan has a transient effect on renal hemodynamics, with increases in glomerular filtration and renal blood flow (RBF) and a decrease in renal vascular resistance (RVR) [5].

Biological context of Retrothiorphan


Anatomical context of Retrothiorphan


Associations of Retrothiorphan with other chemical compounds

  • Enalaprilat, an ACE inhibitor, significantly prevented the rapid degradation of BK and des-Arg9-BK in all species studied, whereas retrothiorphan, a neutral endopeptidase inhibitor, and losartan, an angiotensin II type I receptor antagonist, did not affect this metabolism [8].

Gene context of Retrothiorphan


Analytical, diagnostic and therapeutic context of Retrothiorphan

  • However, a separation of the diastereoisomeric mixtures of these retro-thiorphan derivatives was achieved by HPLC [9].


  1. Complete differentiation between enkephalinase and angiotensin-converting enzyme inhibition by retro-thiorphan. Roques, B.P., Lucas-Soroca, E., Chaillet, P., Costentin, J., Fournié-Zaluski, M.C. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  2. Metabolism of bradykinin by the rat coronary vascular bed. Dumoulin, M.J., Adam, A., Blais, C., Lamontagne, D. Cardiovasc. Res. (1998) [Pubmed]
  3. Thiorphan and retro-thiorphan display equivalent interactions when bound to crystalline thermolysin. Roderick, S.L., Fournie-Zaluski, M.C., Roques, B.P., Matthews, B.W. Biochemistry (1989) [Pubmed]
  4. Effect of endopeptidase-24.11 inhibitors and C-ANP receptor ligand on responses evoked in arterioles of rat cremaster muscle by atrial natriuretic peptide. Peyroux, J., Beslot, F., Claperon, N., Fournie-Zaluski, M.C., Roques, B.P. Br. J. Pharmacol. (1995) [Pubmed]
  5. Effects of the selective neutral endopeptidase inhibitor, retrothiorphan, on renal function and blood pressure in conscious normotensive Wistar and hypertensive DOCA-salt rats. Pham, I., el Amrani, A.I., Fournié-Zaluski, M.C., Corvol, P., Roques, B., Michel, J.B. J. Cardiovasc. Pharmacol. (1992) [Pubmed]
  6. Relationship between the inhibitory potencies of thiorphan and retrothiorphan enantiomers on thermolysin and neutral endopeptidase 24.11 and their interactions with the thermolysin active site by computer modelling. Benchetrit, T., Fournié-Zaluski, M.C., Roques, B.P. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  7. Pharmacological potentiation of natriuretic peptide limits polymorphonuclear neutrophil-vascular cell interactions. Mtairag, e.l. .M., Houard, X., Rais, S., Pasquier, C., Oudghiri, M., Jacob, M.P., Meilhac, O., Michel, J.B. Arterioscler. Thromb. Vasc. Biol. (2002) [Pubmed]
  8. Contribution of angiotensin-converting enzyme to the cardiac metabolism of bradykinin: an interspecies study. Blais, C., Drapeau, G., Raymond, P., Lamontagne, D., Gervais, N., Venneman, I., Adam, A. Am. J. Physiol. (1997) [Pubmed]
  9. 1H NMR configurational correlation for retro-inverso dipeptides: application to the determination of the absolute configuration of "enkephalinase" inhibitors. Relationships between stereochemistry and enzyme recognition. Fournié-Zaluski, M.C., Lucas-Soroca, E., Devin, J., Roques, B.P. J. Med. Chem. (1986) [Pubmed]
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