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Chemical Compound Review

BQ 788     sodium (2R)-2-[[(2R)-2-amino-3-(1...

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Disease relevance of (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid


Psychiatry related information on (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid


High impact information on (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid

  • Intravenous infusion of the ET(B) receptor antagonist BQ-788 caused a small but significant increase in blood pressure in both groups [7].
  • The ETB receptor antagonist BQ-788 (10(-6) M) attenuated the response to ET-3 (10(-10) M), but not that to ET-1 (10(-12) M) [8].
  • Additional experiments indicated that the properistaltic action of endothelin 1 is mediated by enteric neurons, whereas the peristaltic motor effects of sarafotoxin 6c and BQ-788 are caused by a direct action on the muscle [9].
  • The ability of BQ-788 to facilitate peristalsis per se points to a physiologic role of ET(B) receptors in peristaltic motor regulation [9].
  • This vasodilatation was reduced by 95% (P=.006) with inhibition of the endogenous generation of nitric oxide and by 38% (P<.001) with coinfusion of the ET(B) receptor antagonist BQ-788 [10].

Chemical compound and disease context of (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid

  • 1. We investigated the effects of the selective endothelin (ET)A receptor antagonist BQ-485 and the selective ETB receptor antagonist BQ-788 on circulatory failure, multiple organ dysfunction syndrome (MODS) and the alterations in acid base balance caused by endotoxaemia in the anaesthetized rat [11].
  • 1. The effects of intravenous administration of endothelin (ET) receptor antagonists SB-209670 (0.001-10.0 mg kg(-1)), SB-217242, SB-234551 (0.01-10.0 mg kg(-1)) and BQ-788 (0.001-1.0 mg kg(-1)) were investigated on trigeminal nerve ganglion stimulation-induced neurovascular reflexes in the carotid vasculature of the anaesthetized cat [12].
  • 6. Thus, the selective ETB receptor antagonist BQ-788 attenuated (i) the delayed hypotension, (ii) the vascular hyporeactivity to NA as well as (iii) the degree of hepatocellular injury and dysfunction caused by endotoxin in the anaesthetized rat [11].
  • Established peak CION-induced cold hyperalgesia was unaffected by indomethacin and celecoxib, whereas dexamethasone, BQ-123, BQ-788, and i.v. injections of selective antagonists of ET(A) (atrasentan, 3-10 mg/kg) or ET(B) (A-192621, 5-20 mg/kg) receptors caused significant inhibitions lasting 1-2.5h (peaks approximately 65-90%) [13].

Biological context of (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid


Anatomical context of (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid

  • Smooth muscle development in non-crest-derived cell cultures was promoted by endothelin-3 and inhibited by BQ 788 [16].
  • Exposure of PBM to ET-1 markedly reduced the adhesion of these cells to human saphenous vein, whereas PBM adhesion in the presence of BQ-788 was restored to control levels [17].
  • In contrast, BQ-788 did not affect granulocyte infiltration [18].
  • The ET(B) antagonist BQ-788 markedly reduced the secretory response of zona glomerulosa cells and completely suppressed that of zona fasciculata cells, whereas the ET(A) antagonist BQ-123 was ineffective [19].
  • Our results demonstrate that the HSN tumour vasculature is selectively responsive to IRL 1620 at doses > 1 nmol kg(-1) compared with the majority of normal tissues with the exception of the small intestine, and that only the tumour response is highly sensitive to BQ-788 antagonism, under the experimental dosing regime investigated [20].

Associations of (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid with other chemical compounds

  • In rat, an ETA-selective antagonist, BQ-123 (1 mg/kg, i.v.), does not affect transient depressor response to ET-1 (0.3 nmol/kg, i.v.) but potently inhibits following sustained pressor response; vice versa, BQ-788 (1 mg/kg, i.v.) abolishes the depressor response, resulting in a rapid onset of apparently enhanced pressor response [1].
  • The ETA-selective receptor antagonist A-127722 inhibits ET-1-stimulated growth, but the ETB-selective receptor antagonist BQ-788 does not [21].
  • Treatment of THP-1 cells with Trap-14 induced rapid rounding of ameboid cells adherent to fibronectin-coated slides, whereas cell rounding was abrogated in the presence of the nitric oxide synthase inhibitor, NG-nitro-L-arginine or the endothelin B receptor antagonist, BQ-788 [22].
  • Addition of the endothelin type A receptor antagonist BQ-485, but not the endothelin type B receptor antagonist BQ-788, dose-dependently inhibited the effect of endothelin-1 [23].
  • The antagonists used were BQ-123, an ETA antagonist, BQ-788, an ETB antagonist, and SB209670, an ET(A&B) antagonist [18].

Gene context of (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid

  • Biochemical and pharmacological profile of a potent and selective endothelin B-receptor antagonist, BQ-788 [1].
  • Group differences persisted following selective ETB inhibition with BQ-788 (p<0.02), while BQ-123 abolished contractile responses to ET-1 [24].
  • However, simultaneous pre-incubation with BQ-123 (3 microM) and BQ-788 (1 microM) prevented endothelin-1-evoked potentiations, indicative of a role for both ETA and ETB receptors in this system [25].
  • Contractions elicited by IRL 1620 or BQ-3020, but not S6c or ET-3, were sensitive to inhibition by BQ-788 (0.03-3 microM) [26].
  • While, IRL 1620- and ET3-induced InsP1 accumulation was completely blocked by BQ 788, a selective ETB receptor antagonist, in both brain structures evaluated [27].

Analytical, diagnostic and therapeutic context of (2R)-2-[[(2R)-2-amino-3-(1-methoxycarbonylindol-3-yl)propanoyl]-[(2S)-2-[[(2S,6R)-2,6-dimethylpiperidine-1-carbonyl]amino]-4,4-dimethyl-pentanoyl]amino]hexanoic acid

  • Scanning electron microscopy of the peritubular tissue demonstrates that the contractile response to ET was inhibited by a combination of BQ-123 and BQ-788, but not by either antagonist alone [28].
  • The ET(B) antagonist, BQ-788, did not alter the constriction response to CART peptide [29].
  • This BQ-788-induced response was significantly different from that induced by perivascular microinjection of CSF (P < 0.001, analysis of variance) [30].
  • Hemodynamic effects of systemic doses of the ETB-selective antagonist BQ-788 were investigated in 5 healthy male volunteers (age range, 33 to 48 years) in a placebo-controlled, four-way crossover study [15].
  • ETB receptor responsiveness was tested by sarafotoxin S6c concentration-response curves, obtained in the noradrenaline-precontracted mesenteric vascular bed, and repeated after treatment with BQ-788 and after endothelial denudation [31].


  1. Biochemical and pharmacological profile of a potent and selective endothelin B-receptor antagonist, BQ-788. Ishikawa, K., Ihara, M., Noguchi, K., Mase, T., Mino, N., Saeki, T., Fukuroda, T., Fukami, T., Ozaki, S., Nagase, T. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  2. Impaired response of the denervated kidney to endothelin receptor blockade in normotensive and spontaneously hypertensive rats. Girchev, R., Bäcker, A., Markova, P., Kramer, H.J. Kidney Int. (2004) [Pubmed]
  3. Responses to neither exogenous nor endogenous endothelin-1 are altered in patients with hypercholesterolemia. Boak, L.M., Dart, A.M., Duffy, S.J., Chin-Dusting, J.P. J. Lipid Res. (2005) [Pubmed]
  4. Endothelin-1 enhances glutamate-induced retinal cell death, possibly through ETA receptors. Kobayashi, T., Oku, H., Fukuhara, M., Kojima, S., Komori, A., Ichikawa, M., Katsumura, K., Kobayashi, M., Sugiyama, T., Ikeda, T. Invest. Ophthalmol. Vis. Sci. (2005) [Pubmed]
  5. Prolonged endothelin B receptor blockade causes pulmonary hypertension in the ovine fetus. Ivy, D.D., Parker, T.A., Abman, S.H. Am. J. Physiol. Lung Cell Mol. Physiol. (2000) [Pubmed]
  6. Role of endothelin receptor subtypes in the behavioral effects of the intracerebroventricular administration of endothelin-1 in conscious rats. Nagasaka, J., Tsuji, M., Takeda, H., Matsumiya, T. Pharmacol. Biochem. Behav. (1999) [Pubmed]
  7. Systemic hypertension induced by hepatic overexpression of human preproendothelin-1 in rats. Niranjan, V., Télémaque, S., deWit, D., Gerard, R.D., Yanagisawa, M. J. Clin. Invest. (1996) [Pubmed]
  8. Prostaglandin E2 abrogates endothelin-induced vasoconstriction in renal outer medullary descending vasa recta of the rat. Silldorff, E.P., Yang, S., Pallone, T.L. J. Clin. Invest. (1995) [Pubmed]
  9. Regulation of guinea pig intestinal peristalsis by endogenous endothelin acting at ET(B) receptors. Shahbazian, A., Holzer, P. Gastroenterology (2000) [Pubmed]
  10. Endothelin-A receptor antagonist-mediated vasodilatation is attenuated by inhibition of nitric oxide synthesis and by endothelin-B receptor blockade. Verhaar, M.C., Strachan, F.E., Newby, D.E., Cruden, N.L., Koomans, H.A., Rabelink, T.J., Webb, D.J. Circulation (1998) [Pubmed]
  11. Effect of selective blockade of endothelin ETB receptors on the liver dysfunction and injury caused by endotoxaemia in the rat. Ruetten, H., Thiemermann, C. Br. J. Pharmacol. (1996) [Pubmed]
  12. Trigeminal nerve ganglion stimulation-induced neurovascular reflexes in the anaesthetized cat: role of endothelin(B) receptors in carotid vasodilatation. Raval, P., Bingham, S., Aiyar, N., Elliott, J.D., Hunter, A.J., Ohlstein, E.H., Parsons, A.A. Br. J. Pharmacol. (1999) [Pubmed]
  13. Orofacial cold hyperalgesia due to infraorbital nerve constriction injury in rats: reversal by endothelin receptor antagonists but not non-steroidal anti-inflammatory drugs. Chichorro, J.G., Zampronio, A.R., Souza, G.E., Rae, G.A. Pain (2006) [Pubmed]
  14. Stretch-induced endothelin B receptor-mediated apoptosis in vascular smooth muscle cells. Cattaruzza, M., Dimigen, C., Ehrenreich, H., Hecker, M. FASEB J. (2000) [Pubmed]
  15. Systemic blockade of the endothelin-B receptor increases peripheral vascular resistance in healthy men. Strachan, F.E., Spratt, J.C., Wilkinson, I.B., Johnston, N.R., Gray, G.A., Webb, D.J. Hypertension (1999) [Pubmed]
  16. Inhibition of in vitro enteric neuronal development by endothelin-3: mediation by endothelin B receptors. Wu, J.J., Chen, J.X., Rothman, T.P., Gershon, M.D. Development (1999) [Pubmed]
  17. Human monocyte adhesion is modulated by endothelin B receptor-coupled nitric oxide release. King, J.M., Srivastava, K.D., Stefano, G.B., Bilfinger, T.V., Bahou, W.F., Magazine, H.I. J. Immunol. (1997) [Pubmed]
  18. Endothelin receptor antagonists inhibit antigen-induced lung inflammation in mice. Fujitani, Y., Trifilieff, A., Tsuyuki, S., Coyle, A.J., Bertrand, C. Am. J. Respir. Crit. Care Med. (1997) [Pubmed]
  19. Endothelin adrenocortical secretagogue effect is mediated by the B receptor in rats. Belloni, A.S., Rossi, G.P., Andreis, P.G., Neri, G., Albertin, G., Pessina, A.C., Nussdorfer, G.G. Hypertension (1996) [Pubmed]
  20. Modification of blood flow in the HSN tumour and normal tissues of the rat by the endothelin ET(B) receptor agonist, IRL 1620. Bell, K.M., Chaplin, D.J., Poole, B.A., Prise, V.E., Tozer, G.M. Int. J. Cancer (1999) [Pubmed]
  21. Endothelin-1 production and decreased endothelin B receptor expression in advanced prostate cancer. Nelson, J.B., Chan-Tack, K., Hedican, S.P., Magnuson, S.R., Opgenorth, T.J., Bova, G.S., Simons, J.W. Cancer Res. (1996) [Pubmed]
  22. Thrombin receptor activation inhibits monocyte spreading by induction of ET(B) receptor-coupled nitric oxide release. Srivastava, K.D., Magazine, H.I. J. Immunol. (1998) [Pubmed]
  23. Endothelin-1 inhibits nitric oxide synthesis in vascular smooth muscle cells. Ikeda, U., Yamamoto, K., Maeda, Y., Shimpo, M., Kanbe, T., Shimada, K. Hypertension (1997) [Pubmed]
  24. Exaggerated coronary vasoreactivity to endothelin-1 in aged rats: role of protein kinase C. Korzick, D.H., Muller-Delp, J.M., Dougherty, P., Heaps, C.L., Bowles, D.K., Krick, K.K. Cardiovasc. Res. (2005) [Pubmed]
  25. Influence of respiratory tract viral infection on endothelin-1-induced potentiation of cholinergic nerve-mediated contraction in mouse trachea. Carr, M.J., Goldie, R.G., Henry, P.J. Br. J. Pharmacol. (1996) [Pubmed]
  26. Functional and binding characterization of endothelin receptors in human bronchus: evidence for a novel endothelin B receptor subtype? Hay, D.W., Luttmann, M.A., Pullen, M.A., Nambi, P. J. Pharmacol. Exp. Ther. (1998) [Pubmed]
  27. Endothelin ETB receptor signaling in the median eminence and subfornical organ of the rat brain. Garrido, M.d.e.l. .R., Israel, A. Neuropeptides (2004) [Pubmed]
  28. Dual control of seminiferous tubule contractility mediated by ETA and ETB endothelin receptor subtypes. Tripiciano, A., Palombi, F., Ziparo, E., Filippini, A. FASEB J. (1997) [Pubmed]
  29. Cocaine- and amphetamine-regulated transcript (CART) peptide: a vasoactive role in the cerebral circulation. Iliff, J.J., Alkayed, N.J., Gloshani, K.J., Traystman, R.J., West, G.A. J. Cereb. Blood Flow Metab. (2005) [Pubmed]
  30. Endothelin-B receptors in cerebral resistance arterioles and their functional significance after focal cerebral ischemia in cats. Touzani, O., Galbraith, S., Siegl, P., McCulloch, J. J. Cereb. Blood Flow Metab. (1997) [Pubmed]
  31. Functional characterization of endothelin receptors in hypertensive resistance vessels. Montagnani, M., Potenza, M.A., Rinaldi, R., Mansi, G., Nacci, C., Serio, M., Vulpis, V., Pirrelli, A., Mitolo-Chieppa, D. J. Hypertens. (1999) [Pubmed]
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