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Chemical Compound Review

Butaprostum     methyl7-[(1R,2S,3R)-3- hydroxy-2-[(E,4R)-4...

Synonyms: AC1NSJVB, BAY-Q-4218, SureCN94764, CHEMBL271896, B6309_SIGMA, ...
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High impact information on Butaprost


Biological context of Butaprost


Anatomical context of Butaprost


Associations of Butaprost with other chemical compounds

  • Quantitative RT-PCR indicated that the mRNA for the murine EP4 receptor, the butaprost-insensitive PGE2 receptor that couples to Gs, increases 1.5-3-fold in response to serum (NIH 3T3) or LPS (RAW 264.7) with a time course approximating the induction of PGHS-2 expression [15].
  • Furthermore, the EP1 receptor-selective antagonists AH 6809 and SC19220 were more potent than the EP2 receptor-selective agonist butaprost in these competition binding assays [16].
  • PGE2 and the prostaglandin agonists, but not the IP receptor agonist iloprost and the EP2 receptor agonist butaprost, induced a time- and concentration-dependent cAMP accumulation in podocytes [10].
  • Effects on ocular morphology were studied after tissue fixation with transcardial perfusion by paraformaldehyde and immersion fixation of the globe, in animals subjected to long-term treatment with butaprost [12].
  • Only PGE(2) and PGE1 alcohol completely abolished CD36 induction by aspirin, whereas butaprost strongly reduced it [17].

Gene context of Butaprost

  • We now report that both PGE(2) and butaprost increase PTEN phosphatase activity, without a concomitant increase in PTEN protein levels [13].
  • Induction of COX-2 expression was also elicited by butaprost (EP(2) receptor agonist) and 11-deoxy PGE(1) (EP(2)/EP(4) receptor agonist), but not by EP(1)/EP(3) receptor agonists (17-phenyl-omega-trinor PGE(2), sulprostone) [18].
  • Butaprost, a selective EP2 agonist, and ONO-AE1-329, a selective EP4 agonist, significantly inhibited IL-1alpha-induced MMP-3 production, although butaprost was less potent than ONO-AE-1-329 [19].
  • The EP4 receptor-specific agonist, 11-deoxy-PGE1, induced a time-dependent phosphorylation of protein kinase C and extracellular signal-regulated kinase (ERK) 1/2 in serum-depleted (0.1%) VSMCs, whereas the EP2 receptor agonist, butaprost, was without effect [20].
  • The EP1 selective agonist iloprost and the EP2 selective agonist butaprost minimally stimulated RANKL [21].

Analytical, diagnostic and therapeutic context of Butaprost

  • The effects of butaprost on aqueous humor flow were determined by fluorophotometry [12].
  • The eyes of separate groups of EP(1) receptor knockout and wild type mice were: 1) treated topically with prostaglandin E(2) (PGE(2)) or the EP(2) receptor selective agonist, butaprost; 2) given intravitreal injection of LPS; or 3) paracentesis performed [22].


  1. Prostaglandin E(2) stimulates rat and human colonic mucin exocytosis via the EP(4) receptor. Belley, A., Chadee, K. Gastroenterology (1999) [Pubmed]
  2. Comparison of prostaglandin F2alpha, bimatoprost (prostamide), and butaprost (EP2 agonist) on Cyr61 and connective tissue growth factor gene expression. Liang, Y., Li, C., Guzman, V.M., Evinger, A.J., Protzman, C.E., Krauss, A.H., Woodward, D.F. J. Biol. Chem. (2003) [Pubmed]
  3. Effects of mechanical strain on the function of Gap junctions in osteocytes are mediated through the prostaglandin EP2 receptor. Cherian, P.P., Cheng, B., Gu, S., Sprague, E., Bonewald, L.F., Jiang, J.X. J. Biol. Chem. (2003) [Pubmed]
  4. The expression of prostaglandin E receptors EP2 and EP4 and their different regulation by lipopolysaccharide in C3H/HeN peritoneal macrophages. Ikegami, R., Sugimoto, Y., Segi, E., Katsuyama, M., Karahashi, H., Amano, F., Maruyama, T., Yamane, H., Tsuchiya, S., Ichikawa, A. J. Immunol. (2001) [Pubmed]
  5. Prostaglandin E2 alters human orbital fibroblast shape through a mechanism involving the generation of cyclic adenosine monophosphate. Wang, H.S., Keese, C.R., Giaever, I., Smith, T.J. J. Clin. Endocrinol. Metab. (1995) [Pubmed]
  6. Prostaglandin E(2) protects human lung fibroblasts from cigarette smoke extract-induced apoptosis via EP(2) receptor activation. Sugiura, H., Liu, X., Togo, S., Kobayashi, T., Shen, L., Kawasaki, S., Kamio, K., Wang, X.Q., Mao, L.J., Rennard, S.I. J. Cell. Physiol. (2007) [Pubmed]
  7. Prostaglandin E2 EP2 and EP4 receptor activation mediates cAMP-dependent hyperpolarization and exocytosis of renin in juxtaglomerular cells. Friis, U.G., Stubbe, J., Uhrenholt, T.R., Svenningsen, P., Nüsing, R.M., Skøtt, O., Jensen, B.L. Am. J. Physiol. Renal Physiol. (2005) [Pubmed]
  8. Prostaglandin E2 modulates dendritic cell function via EP2 and EP4 receptor subtypes. Harizi, H., Grosset, C., Gualde, N. J. Leukoc. Biol. (2003) [Pubmed]
  9. Upregulation of orphan nuclear receptor Nur77 following PGF(2alpha), Bimatoprost, and Butaprost treatments. Essential role of a protein kinase C pathway involved in EP(2) receptor activated Nur77 gene transcription. Liang, Y., Li, C., Guzman, V.M., Chang, W.W., Evinger, A.J., Pablo, J.V., Woodward, D.F. Br. J. Pharmacol. (2004) [Pubmed]
  10. Characterization of prostanoid receptors in podocytes. Bek, M., Nüsing, R., Kowark, P., Henger, A., Mundel, P., Pavenstädt, H. J. Am. Soc. Nephrol. (1999) [Pubmed]
  11. Cloning of a novel human prostaglandin receptor with characteristics of the pharmacologically defined EP2 subtype. Regan, J.W., Bailey, T.J., Pepperl, D.J., Pierce, K.L., Bogardus, A.M., Donello, J.E., Fairbairn, C.E., Kedzie, K.M., Woodward, D.F., Gil, D.W. Mol. Pharmacol. (1994) [Pubmed]
  12. The prostanoid EP2 receptor agonist butaprost increases uveoscleral outflow in the cynomolgus monkey. Nilsson, S.F., Drecoll, E., Lütjen-Drecoll, E., Toris, C.B., Krauss, A.H., Kharlamb, A., Nieves, A., Guerra, T., Woodward, D.F. Invest. Ophthalmol. Vis. Sci. (2006) [Pubmed]
  13. Prostaglandin E(2) inhibits fibroblast migration by E-prostanoid 2 receptor-mediated increase in PTEN activity. White, E.S., Atrasz, R.G., Dickie, E.G., Aronoff, D.M., Stambolic, V., Mak, T.W., Moore, B.B., Peters-Golden, M. Am. J. Respir. Cell Mol. Biol. (2005) [Pubmed]
  14. Investigation of the prostacyclin (IP) receptor antagonist RO1138452 on isolated blood vessel and platelet preparations. Jones, R.L., Wise, H., Clark, R., Whiting, R.L., Bley, K.R. Br. J. Pharmacol. (2006) [Pubmed]
  15. Prostanoid receptors of murine NIH 3T3 and RAW 264.7 cells. Structure and expression of the murine prostaglandin EP4 receptor gene. Arakawa, T., Laneuville, O., Miller, C.A., Lakkides, K.M., Wingerd, B.A., DeWitt, D.L., Smith, W.L. J. Biol. Chem. (1996) [Pubmed]
  16. Cloning and expression of a cDNA for the human prostaglandin E receptor EP1 subtype. Funk, C.D., Furci, L., FitzGerald, G.A., Grygorczyk, R., Rochette, C., Bayne, M.A., Abramovitz, M., Adam, M., Metters, K.M. J. Biol. Chem. (1993) [Pubmed]
  17. Aspirin increases CD36, SR-BI, and ABCA1 expression in human THP-1 macrophages. Viñals, M., Bermúdez, I., Llaverias, G., Alegret, M., Sanchez, R.M., Vázquez-Carrera, M., Laguna, J.C. Cardiovasc. Res. (2005) [Pubmed]
  18. Prostaglandin E2 induces cyclooxygenase-2 expression in human non-pigmented ciliary epithelial cells through activation of p38 and p42/44 mitogen-activated protein kinases. Rösch, S., Ramer, R., Brune, K., Hinz, B. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
  19. Cyclooxygenase-2-dependent prostaglandin (PG) E2 downregulates matrix metalloproteinase-3 production via EP2/EP4 subtypes of PGE2 receptors in human periodontal ligament cells stimulated with interleukin-1alpha. Yan, M., Noguchi, K., Ruwanpura, S.M., Ishikawa, I. J. Periodontol. (2005) [Pubmed]
  20. Prostacyclin induces apoptosis of vascular smooth muscle cells by a cAMP-mediated inhibition of extracellular signal-regulated kinase activity and can counteract the mitogenic activity of endothelin-1 or basic fibroblast growth factor. Li, R.C., Cindrova-Davies, T., Skepper, J.N., Sellers, L.A. Circ. Res. (2004) [Pubmed]
  21. Fibroblasts express RANKL and support osteoclastogenesis in a COX-2-dependent manner after stimulation with titanium particles. Wei, X., Zhang, X., Zuscik, M.J., Drissi, M.H., Schwarz, E.M., O'Keefe, R.J. J. Bone Miner. Res. (2005) [Pubmed]
  22. Modulation of ocular inflammatory responses by EP(1) receptors in mice. Biswas, S., Bhattacherjee, P., Paterson, C.A., Maruyama, T., Narumiya, S. Exp. Eye Res. (2007) [Pubmed]
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