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Chemical Compound Review

dinoprost     (Z)-7-[(1R,2S,3R,5S)-3,5- dihydroxy-2-[(E...

Synonyms: cyclosin, Enzaprost F, PGF2, PGF2alpha, PGF2 alpha, ...
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Disease relevance of Enzaprost F


Psychiatry related information on Enzaprost F


High impact information on Enzaprost F


Chemical compound and disease context of Enzaprost F


Biological context of Enzaprost F


Anatomical context of Enzaprost F


Associations of Enzaprost F with other chemical compounds

  • In many nonprimate mammalian species, cyclical regression of the corpus luteum (luteolysis) is caused by the episodic pulsatile secretion of uterine PGF2alpha, which acts either locally on the corpus luteum by a countercurrent mechanism or, in some species, via the systemic circulation [11].
  • Endogenous phospholipase A2 activity of brain synaptic vesicles was Ca2+ -dependent and was increased by prostaglandin F2 alpha, calmodulin, adenosine 3', 5' -monophosphate, and adenosine triphosphate, whereas the activity was inhibited by prostaglandin E2 in the absence or presence of calmodulin [26].
  • None of the stable cyclooxygenase products of 20:4 (6-keto PGF1 alpha, PGF2 alpha, PGE2, TXB2) nor polar metabolites of mono-HETEs are either incorporated or metabolized [27].
  • In this study the airways effects of 9 alpha,11 beta-PGF2 were compared with those of its epimer 9 alpha,11 alpha-PGF2 (PGF2 alpha) and PGD2 [28].
  • Keratinocyte cultures incubated with [14C]arachidonic acid synthesized prostaglandin (PG)E2 PGD2, PGF2 alpha, and small quantities of 6-keto-F1 alpha [29].

Gene context of Enzaprost F

  • Measurement of uterine PGs further confirmed that COX-1 accounted for the majority of PGF2alpha production [30].
  • In contrast, simultaneous oxytocin and COX-1 deficiency restored the normal onset of labor by allowing luteolysis in the absence of elevated PGF2alpha production [30].
  • Finally, we confirmed that PGF2alpha could potentiate angiogenesis in endometrial adenocarcinoma explants by transactivation of the EGFR and induction of VEGF mRNA expression [31].
  • The binding was displaced with unlabeled PGs in the order of PGF2 alpha = 9 alpha, 11 beta PGF2 > PGF 1 alpha > PGD2 > STA2 (a stable TXA2 agonist) > PGE2 > iloprost (a stable PGI2 agonist) [32].
  • LIF and OSM specifically trigger STAT1 cytoplasmic to nuclear translocation, whereas PGF2alpha fails to do so [33].
  • We show that PGF2alpha increases expression of the inhibitor of apoptosis protein (IAP) BRUCE through a pathway dependent on the nuclear factor of activated T cell 2 transcription factor [34].

Analytical, diagnostic and therapeutic context of Enzaprost F


  1. Thromboxane A2 and prostaglandin F2alpha mediate inflammatory tachycardia. Takayama, K., Yuhki, K., Ono, K., Fujino, T., Hara, A., Yamada, T., Kuriyama, S., Karibe, H., Okada, Y., Takahata, O., Taniguchi, T., Iijima, T., Iwasaki, H., Narumiya, S., Ushikubi, F. Nat. Med. (2005) [Pubmed]
  2. The prostaglandins. Clayman, C.B. JAMA (1975) [Pubmed]
  3. Effect of simulated systemic administration of aspirin, salicylate, and indomethacin on amphibian gastric mucosa. Rowe, P.H., Starlinger, M.J., Kasdon, E., Marrone, G., Silen, W. Gastroenterology (1986) [Pubmed]
  4. Local prostaglandin F2 alpha injection for termination of ectopic pregnancy. Lindblom, B., Hahlin, M., Källfelt, B., Hamberger, L. Lancet (1987) [Pubmed]
  5. Abnormal levels of prostaglandins and fatty acids in blood of children with cystic fibrosis. Chase, H.P., Dupont, J. Lancet (1978) [Pubmed]
  6. Oxytocin induces maternal behavior in virgin female rats. Pedersen, C.A., Ascher, J.A., Monroe, Y.L., Prange, A.J. Science (1982) [Pubmed]
  7. Prostaglandin D2, a cerebral sleep-inducing substance in rats. Ueno, R., Honda, K., Inoué, S., Hayaishi, O. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  8. Bronchial response to inhaled prostaglandin F2alpha in patients with common or aspirin-sensitive asthma. Orehek, J., Gayrard, P., Grimaud, C., Charpin, J. J. Allergy Clin. Immunol. (1977) [Pubmed]
  9. Prostaglandins masculinize the mouse genital tract. Gupta, C. Endocrinology (1989) [Pubmed]
  10. Effects of intracerebroventricular administration of prostaglandin D2 on behaviour, blood pressure and body temperature as compared to prostaglandins E2 and F2 alpha. Förstermann, U., Heldt, R., Hertting, G. Psychopharmacology (Berl.) (1983) [Pubmed]
  11. Luteolysis: a neuroendocrine-mediated event. McCracken, J.A., Custer, E.E., Lamsa, J.C. Physiol. Rev. (1999) [Pubmed]
  12. Uterine luteolytic hormone: a physiological role for prostaglandin F2alpha. Horton, E.W., Poyser, N.L. Physiol. Rev. (1976) [Pubmed]
  13. EGF, PGF2 alpha and insulin induce the phosphorylation of identical S6 peptides in swiss mouse 3T3 cells: effect of cAMP on early sites of phosphorylation. Martin-Pérez, J., Siegmann, M., Thomas, G. Cell (1984) [Pubmed]
  14. Altered renal and platelet arachidonic acid metabolism in cirrhosis. Laffi, G., La Villa, G., Pinzani, M., Ciabattoni, G., Patrignani, P., Mannelli, M., Cominelli, F., Gentilini, P. Gastroenterology (1986) [Pubmed]
  15. Effect of hypercholesterolemia on vascular reactivity in the rabbit. I. Endothelium-dependent and endothelium-independent contractions and relaxations in isolated arteries of control and hypercholesterolemic rabbits. Verbeuren, T.J., Jordaens, F.H., Zonnekeyn, L.L., Van Hove, C.E., Coene, M.C., Herman, A.G. Circ. Res. (1986) [Pubmed]
  16. Inhibitory effect of prostaglandin F2 alpha on the growth of a hormone-dependent rat mammary tumor. Jubiz, W., Frailey, J., Smith, J.B. Cancer Res. (1979) [Pubmed]
  17. Release of prostanoids into the portal and hepatic vein in patients with chronic liver disease. Wernze, H., Tittor, W., Goerig, M. Hepatology (1986) [Pubmed]
  18. Failure of parturition in mice lacking the prostaglandin F receptor. Sugimoto, Y., Yamasaki, A., Segi, E., Tsuboi, K., Aze, Y., Nishimura, T., Oida, H., Yoshida, N., Tanaka, T., Katsuyama, M., Hasumoto, K., Murata, T., Hirata, M., Ushikubi, F., Negishi, M., Ichikawa, A., Narumiya, S. Science (1997) [Pubmed]
  19. Localization of distinct F2-isoprostanes in human atherosclerotic lesions. Praticò, D., Iuliano, L., Mauriello, A., Spagnoli, L., Lawson, J.A., Rokach, J., Maclouf, J., Violi, F., FitzGerald, G.A. J. Clin. Invest. (1997) [Pubmed]
  20. Prostaglandins regulate the synthesis and secretion of the atrial natriuretic peptide. Gardner, D.G., Schultz, H.D. J. Clin. Invest. (1990) [Pubmed]
  21. Cervical ripening and induction of labour with intravaginal prostaglandin F2 alpha. MacLennan, A.H., Green, R.C. Lancet (1979) [Pubmed]
  22. Prostaglandin F2(alpha) stimulates growth of skeletal muscle cells via an NFATC2-dependent pathway. Horsley, V., Pavlath, G.K. J. Cell Biol. (2003) [Pubmed]
  23. Adherence of human peripheral blood lymphycytes to measles-infected cells. Enhancement by prostaglandin E1. Zurier, R.B., Dore-Duffy, P., Viola, M.V. N. Engl. J. Med. (1977) [Pubmed]
  24. Possible role of prostaglandin F2alpha in mediating effect of prolactin on RNA synthesis in mammary gland explants of mice. Rillema, J.A. Nature (1975) [Pubmed]
  25. Inhibitory role of the endothelium in the response of isolated coronary arteries to platelets. Cohen, R.A., Shepherd, J.T., Vanhoutte, P.M. Science (1983) [Pubmed]
  26. Interaction of brain synaptic vesicles induced by endogenous Ca2+ -dependent phospholipase A2. Moskowitz, N., Schook, W., Puszkin, S. Science (1982) [Pubmed]
  27. Uptake and metabolism of monohydroxy-eicosatetraenoic acids by macrophages. Pawlowski, N.A., Scott, W.A., Andreach, M., Cohn, Z.A. J. Exp. Med. (1982) [Pubmed]
  28. 9 alpha,11 beta-prostaglandin F2, a novel metabolite of prostaglandin D2 is a potent contractile agonist of human and guinea pig airways. Beasley, C.R., Robinson, C., Featherstone, R.L., Varley, J.G., Hardy, C.C., Church, M.K., Holgate, S.T. J. Clin. Invest. (1987) [Pubmed]
  29. Modulation of keratinocyte proliferation in vitro by endogenous prostaglandin synthesis. Pentland, A.P., Needleman, P. J. Clin. Invest. (1986) [Pubmed]
  30. Opposing actions of prostaglandins and oxytocin determine the onset of murine labor. Gross, G.A., Imamura, T., Luedke, C., Vogt, S.K., Olson, L.M., Nelson, D.M., Sadovsky, Y., Muglia, L.J. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  31. A novel angiogenic role for prostaglandin F2alpha-FP receptor interaction in human endometrial adenocarcinomas. Sales, K.J., List, T., Boddy, S.C., Williams, A.R., Anderson, R.A., Naor, Z., Jabbour, H.N. Cancer Res. (2005) [Pubmed]
  32. Cloning and expression of a cDNA for mouse prostaglandin F receptor. Sugimoto, Y., Hasumoto, K., Namba, T., Irie, A., Katsuyama, M., Negishi, M., Kakizuka, A., Narumiya, S., Ichikawa, A. J. Biol. Chem. (1994) [Pubmed]
  33. Leukemia inhibitory factor induces DNA synthesis in Swiss mouse 3T3 cells independently of cyclin D1 expression through a mechanism involving MEK/ERK1/2 activation. Dekanty, A., Sauane, M., Cadenas, B., Coluccio, F., Barrio, M., Casala, J., Paciencia, M., Rogers, F., Coso, O.A., Piwien-Pilipuk, G., Rudland, P.S., de Asúa, L.J. J. Biol. Chem. (2006) [Pubmed]
  34. Prostaglandin F2alpha promotes muscle cell survival and growth through upregulation of the inhibitor of apoptosis protein BRUCE. Jansen, K.M., Pavlath, G.K. Cell Death Differ. (2008) [Pubmed]
  35. Interaction of vasopressin and prostaglandins in the toad urinary bladder. Bisordi, J.E., Schlondorff, D., Hays, R.M. J. Clin. Invest. (1980) [Pubmed]
  36. Platelet-induced neurogenic coronary contractions due to accumulation of the false neurotransmitter, 5-hydroxytryptamine. Cohen, R.A. J. Clin. Invest. (1985) [Pubmed]
  37. Hypotension and reduced nitric oxide-elicited vasorelaxation in transgenic mice overexpressing endothelial nitric oxide synthase. Ohashi, Y., Kawashima, S., Hirata, K., Yamashita, T., Ishida, T., Inoue, N., Sakoda, T., Kurihara, H., Yazaki, Y., Yokoyama, M. J. Clin. Invest. (1998) [Pubmed]
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