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Chemical Compound Review

D0400_SIGMA     (Z)-7-[(1S,4S,5R,6S)-6- [(E,3S)-3...

Synonyms: U-44069, U44069, U 44069, 56985-32-1
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Disease relevance of U 44069

  • Treatment of membranes with either cholera or pertussis toxins, which inhibited markedly the receptor-mediated stimulation of the GTPase activities of Ns and Ni respectively, had no or only a small effect, respectively, on the GTPase activity stimulated by PAF and U44069 [1].
  • Acute, stable pulmonary hypertension was induced in instrumented unanesthetized sheep by infusing a PGH(2) analog, U-44069 [2].

High impact information on U 44069


Chemical compound and disease context of U 44069


Biological context of U 44069


Anatomical context of U 44069


Associations of U 44069 with other chemical compounds

  • Nifedipine also reversed the U44069-induced AA constriction (81 +/- 7%), but failed to inhibit the EA constriction at concentrations from 10(-9) to 10(-6) mol/L [6].
  • The variations in the formation of 3H-PA in this patient on different occasions broadly paralleled the variations in the initial rates of ADP and U44069 aggregation and in epinephrine aggregation seen in PRP [17].
  • 5. In vessel rings submaximally contracted with the thromboxane analogue U44069 (2 microM), the selective alpha 2-adrenoceptor agonist UK14304 induced concentration-dependent relaxation, which was abolished by removal of endothelium [18].
  • When L-640,035 was administered intravenously to guinea-pigs, significant inhibition of increases in pulmonary resistance or insufflation pressure induced by U-44069 (ED50 0.16 mg kg-1), leukotriene D4 (ED50 0.25 mg kg-1) and 5-HT (ED50 3.4 mg kg-1) but not histamine (ED50 greater than 10 mg kg-1) was observed [19].
  • Intravenous injections of the TXA2 receptor mimics, U-46619 [(15S)-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta5Z,13E-dienoic acid] and U-44069 (9,11-dideoxy-11 alpha,9 alpha-epoxymethano PGF2 alpha), produced dose-related increases in transpulmonary pressure and lung resistance and decreases in dynamic compliance [20].

Gene context of U 44069

  • A high-resolution NMR spectroscopy was used to determine the conformational changes and solution 3D structure of U44069, a PGH(2) analogue, bound to one of the COX-downstream synthases-an engineered thromboxane A(2) synthase (TXAS) [21].
  • Moreover, ANG II (10(-11) - 10(-7) M) augmented platelet responses to the TxA2 mimetic, U44069 [22].
  • Both 5-hydroxy-tryptamine and beta-thromboglobulin release were greater with patients' platelets than with those of controls in response to adrenaline, ADP and U44069 [23].
  • Treatment with another PGH(2) analogue, U44069, produced a peak at 387 nm and a trough at 432 nm in the spectrum (Type I), while treatment with tranylcypromine, a PGIS inhibitor, produced a peak at 434 nm and a trough at 412 nm (Type II) [24].
  • 2. Contractile responses were elicited in aortic rings that were either: (i) precontracted submaximally with the thromboxane A2 agonist U44069 in order to amplify the responses; or (ii) exposed to N(omega)-nitro-L-arginine (100 micromol/L) plus LY 53857 (0.1 micromol/L; a 5-HT2 receptor antagonist shown previously to inhibit relaxation) [25].

Analytical, diagnostic and therapeutic context of U 44069

  • The effects of a thromboxane A2 (TxA2)-endoperoxide analogue, U-44069 (0.16 micrograms/min. i.a.) on blood flows to the total wall, the mucosal (= mucosa+submucosa), and muscularis (= muscularis+serosa) layers of the canine jejunum, were determined utilizing radiolabelled microspheres (diam = 13.75 microns) [26].
  • When administered to the IPRK, 10(-6) M U-44069 caused a 82 +/- 3% decrease in glomerular filtration rate (GFR) and a 80 +/- 4% decrease in filtration fraction but reduced renal perfusate flow (RPF) only 13 +/- 8% (P less than 0.005) [27].


  1. Platelet activating factor and U44069 stimulate a GTPase activity in human platelets which is distinct from the guanine nucleotide regulatory proteins, Ns and Ni. Houslay, M.D., Bojanic, D., Wilson, A. Biochem. J. (1986) [Pubmed]
  2. Potent effects of aerosol compared with intravenous treprostinil on the pulmonary circulation. Sandifer, B.L., Brigham, K.L., Lawrence, E.C., Mottola, D., Cuppels, C., Parker, R.E. J. Appl. Physiol. (2005) [Pubmed]
  3. Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides. Bylund, J., Hidestrand, M., Ingelman-Sundberg, M., Oliw, E.H. J. Biol. Chem. (2000) [Pubmed]
  4. Xenobiotic-metabolizing cytochromes P450 convert prostaglandin endoperoxide to hydroxyheptadecatrienoic acid and the mutagen, malondialdehyde. Plastaras, J.P., Guengerich, F.P., Nebert, D.W., Marnett, L.J. J. Biol. Chem. (2000) [Pubmed]
  5. Evidence for the involvement of the thromboxane synthase pathway in human natural cytotoxic cell activity. Rola-Pleszczynski, M., Gagnon, L., Bolduc, D., LeBreton, G. J. Immunol. (1985) [Pubmed]
  6. Direct evidence that thromboxane mimetic U44069 preferentially constricts the afferent arteriole. Hayashi, K., Loutzenhiser, R., Epstein, M. J. Am. Soc. Nephrol. (1997) [Pubmed]
  7. Intravenous endotoxin triggers pulmonary vasoconstriction and pulmonary hypertension in broiler chickens. Wideman, R.F., Erf, G.F., Chapman, M.E. Poult. Sci. (2001) [Pubmed]
  8. Quinones. 4. Novel eicosanoid antagonists: synthesis and pharmacological evaluation. Shiraishi, M., Kato, K., Terao, S., Ashida, Y., Terashita, Z., Kito, G. J. Med. Chem. (1989) [Pubmed]
  9. Inhibition of prostanoid-mediated platelet aggregation in vivo and in vitro by 3-hydroxymethyl-dibenzo(b,f)thiepin 5,5-dioxide (L-640,035). Chan, C.C., Nathaniel, D.J., Yusko, P.J., Hall, R.A., Ford-Hutchinson, A.W. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  10. Thromboxane A2-mimetics are potent microvascular permeability factors in the conjunctiva. Woodward, D.F., Nieves, A.L., Williams, L.S. J. Pharmacol. Exp. Ther. (1990) [Pubmed]
  11. In vivo effects of a novel thromboxane A2/prostaglandin H2 (TXA2/PGH2) partial agonist, (+)5(Z)-7-[3-endo-phenylsulfonylamino[2.2.1]- bicyclohept-2-exo-yl]-heptenoic acid [(+)-S-145], on vascular, platelet and cardiac function. Dubé, G.P., Jakubowski, J.A., Brune, K.A., Bemis, K.G., Kurtz, W.L. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  12. Nonadrenergic noncholinergic relaxation of human pulmonary arteries is partially mediated by nitric oxide. Scott, J.A., Craig, I., McCormack, D.G. Am. J. Respir. Crit. Care Med. (1996) [Pubmed]
  13. Responses of isolated feline and human cerebral arteries to prostacyclin and some of its metabolites. Uski, T., Andersson, K.E., Brandt, L., Edvinsson, L., Ljunggren, B. J. Cereb. Blood Flow Metab. (1983) [Pubmed]
  14. Differential antagonism of airway contractile responses to prostaglandin (PG)D2 and 9 alpha, 11 beta-PGF2 by atropine, SK&F 88046 and SQ 29,548 in the guinea pig. Underwood, D.C., Muccitelli, R.M., Luttmann, M.A., Hay, D.W., Torphy, T.J., Wasserman, M.A. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  15. Endothelium-dependent nonadrenergic, noncholinergic neural relaxation in guinea pig pulmonary artery. Liu, S.F., Crawley, D.E., Evans, T.W., Barnes, P.J. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
  16. Differential effects of epithelium removal on the responsiveness of guinea-pig tracheal smooth muscle to bronchoconstrictors. Hay, D.W., Farmer, S.G., Raeburn, D., Muccitelli, R.M., Wilson, K.A., Fedan, J.S. Br. J. Pharmacol. (1987) [Pubmed]
  17. Impairment of phosphatidylinositol metabolism in a patient with a bleeding disorder associated with defects of initial platelet responses. Lages, B., Weiss, H.J. Thromb. Haemost. (1988) [Pubmed]
  18. Endogenous nitric oxide modulates adrenergic neural vasoconstriction in guinea-pig pulmonary artery. Liu, S.F., Crawley, D.E., Evans, T.W., Barnes, P.J. Br. J. Pharmacol. (1991) [Pubmed]
  19. Studies on L-640,035: a novel antagonist of contractile prostanoids in the lung. Carrier, R., Cragoe, E.J., Ethier, D., Ford-Hutchinson, A.W., Girard, Y., Hall, R.A., Hamel, P., Rokach, J., Share, N.N., Stone, C.A. Br. J. Pharmacol. (1984) [Pubmed]
  20. Influence of SK&F 95587 and BN 50730 on bronchoconstrictor responses in the cat. Dyson, M.C., Bellan, J.A., Minkes, R.K., Beckerman, R.C., Wegmann, M.J., Braquet, P., McNamara, D.B., Kadowitz, P.J. J. Pharmacol. Exp. Ther. (1990) [Pubmed]
  21. Solution structure of a common substrate mimetic of cyclooxygenase-downstream synthases bound to an engineered thromboxane A2 synthase using a high-resolution NMR technique. Ruan, K.H., Wu, J., Wang, L.H. Arch. Biochem. Biophys. (2005) [Pubmed]
  22. Potentiation of adrenaline-induced platelet aggregation by angiotensin II. Ding, Y.A., MacIntyre, D.E., Kenyon, C.J., Semple, P.F. Thromb. Haemost. (1985) [Pubmed]
  23. Platelet thromboxane synthesis and release reactions in myeloproliferative disorders. Smith, I.L., Martin, T.J. Haemostasis (1982) [Pubmed]
  24. Purification and characterization of recombinant human prostacyclin synthase. Wada, M., Yokoyama, C., Hatae, T., Shimonishi, M., Nakamura, M., Imai, Y., Ullrich, V., Tanabe, T. J. Biochem. (2004) [Pubmed]
  25. 5-Hydroxytryptamine-induced contraction of the marmoset aorta is mediated by a 5-HT1-like receptor. Dyer, S.M., de la Lande, I.S., Frewin, D.B., Head, R.J. Clin. Exp. Pharmacol. Physiol. (1998) [Pubmed]
  26. Differences in vascular response to thromboxane between intestinal mucosa and muscularis. Alemayehu, A., Chou, C.C. Prostaglandins (1993) [Pubmed]
  27. Reversal of renal and smooth muscle actions of the thromboxane mimetic U-44069 by diltiazem. Loutzenhiser, R., Epstein, M., Horton, C., Sonke, P. Am. J. Physiol. (1986) [Pubmed]
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