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Chemical Compound Review

SureCN3344355     (Z)-5-[(2S,3S,4S)-4,6- dihydroxy-2-[(E,3S)...

Synonyms: HMDB02904, BML2-G02, LMFA03030003, AC1NR1LW, 2,3-Dinor-TXB2, ...
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Disease relevance of LMFA03030003


High impact information on LMFA03030003


Chemical compound and disease context of LMFA03030003


Biological context of LMFA03030003

  • Women whose pregnancies ended in abortion had higher (p less than 0.05) output of 2,3-dinor-TxB2 between weeks 4 and 7 of gestation and lower (p less than 0.01) excretion of 2,3-dinor-6-keto-PGF1 alpha between weeks 8 and 11 compared with women whose pregnancies proceeded to term [1].
  • It is suggested that the cause of the increased urinary excretion of 2,3-dinor-TxB2 is the consequence of intrarenal platelet and macrophage activation, probably triggered by the endothelial damage [11].
  • Co-administration of ASA significantly inhibits 2,3-dinor-TXB2 excretion, but does not interfere with the blood pressure lowering effect of captopril in healthy human subjects [12].
  • No significant increase in 11-dh-TXB2 was observed after TXB2 injection (10 micrograms/kg) in dogs, but the 2,3-dinor-TXB2 level rose significantly, its AUC ratio to TXB2 being 0.29, comparable with that in rabbits [13].

Anatomical context of LMFA03030003


Associations of LMFA03030003 with other chemical compounds

  • However, the combination of Ro 44-9883 and Ro 46-6240 reduced the time to reperfusion (40 +/- 8 vs. 68 +/- 15 min; n = 7, P < .05), prevented reocclusion and abolished the rise in urinary 2,3-dinor-TXB2 (5 +/- 1 ng/mg creatinine, n = 4) [16].
  • The influence of a submaximal exercise on urinary 2,3-dinor-6-ketoprostaglandin F1 alpha (2,3-dinor-6-keto-PGF1 alpha), 2,3-dinor-thromboxane B2 (2,3-dinor-TxB2), and prostaglandin E2 excretion and on platelet aggregation was compared in untrained and trained subjects before and after low-dose aspirin administration (50 mg/day, 7 days) [17].
  • L-ARG infusion also inhibited platelet TXB2 formation and slightly, but not significantly decreased the urinary excretion rate of 2,3-dinor-TXB2; cGMP concentrations in PRP were significantly elevated during L-arginine infusion [18].
  • The cyclooxygenase inhibitor indomethacin given by infusion in anaesthetized dogs (2.5, 8 and 25 micrograms/kg/min) dose-dependently inhibited 2,3-dinor TXB2 excretion measured by IA/GC-MS, with maximal inhibition (83.0 +/- 4.2%) being achieved after 6h (25 micrograms/kg/min) [19].
  • The beneficial effects of indomethacin may be due to its ability to prevent the elevation of platelet aggregation, TXA2 (measured as urinary 2,3-dinor-TXB2 excretion) and 8-iso-PGF2alpha formation and to retard the decrease in endogenous nitric oxide synthesis (assessed as urinary excretion of nitrate) [20].

Gene context of LMFA03030003

  • Selective inhibition of COX-1 reduced 2,3-dinor-TXB2 generation and lesion formation [21].
  • Parameters investigated: CIn, CPAH, TxB2 in plasma, serum and urine; 6-oxo-PGF1 alpha in plasma and urine, urinary 2,3-dinor-TxB2 excretion [22].
  • Despite marked changes in urine flow, GFR, urinary pH, osmolality, sodium and potassium excretion, only a insignificant or transient rise in the enzymatic prostanoid metabolites (2,3-dinor-6-keto-PGF1 alpha, PGE-M, 2,3-dinor-TxB2 and 11-dehydro-TxB2) was observed [23].
  • A method for measurement of PGF2 alpha, PGE1, PGE2, 6-keto-PGF1 alpha, TXB2, 2,3-dinor-TXB2 as well as 5-, 8-, 9-, 11-, 12-, 15-HETE and HHT, utilizing negative ion chemical ionization GC/MS is presented [24].

Analytical, diagnostic and therapeutic context of LMFA03030003


  1. Thromboxane dominance and prostacyclin deficiency in habitual abortion. Tulppala, M., Viinikka, L., Ylikorkala, O. Lancet (1991) [Pubmed]
  2. Thromboxane A2 and prostacyclin biosynthesis in children and adolescents with pulmonary vascular disease. Adatia, I., Barrow, S.E., Stratton, P.D., Miall-Allen, V.M., Ritter, J.M., Haworth, S.G. Circulation (1993) [Pubmed]
  3. Defective aggregation in cirrhosis is independent of in vivo platelet activation. Laffi, G., Cinotti, S., Filimberti, E., Ciabattoni, G., Caporale, R., Marra, F., Melani, L., Grossi, A., Carloni, V., Gentilini, P. J. Hepatol. (1996) [Pubmed]
  4. Increased renal TXA2 synthesis in diabetes mellitus: simultaneous determination of urinary TXB2 and 2,3-dinor-TXB2. Katayama, S., Inaba, M., Maruno, Y., Omoto, A., Kawazu, S., Ishii, J., Sawada, M. Prostaglandins Leukot. Essent. Fatty Acids (1990) [Pubmed]
  5. In vivo production of thromboxane in acute human myocardial infarction: a preliminary study. Vesterqvist, O., Edhag, O., Green, K., Henriksson, P. Thromb. Res. (1985) [Pubmed]
  6. Transdermal modification of platelet function. A dermal aspirin preparation selectively inhibits platelet cyclooxygenase and preserves prostacyclin biosynthesis. Keimowitz, R.M., Pulvermacher, G., Mayo, G., Fitzgerald, D.J. Circulation (1993) [Pubmed]
  7. Replacement of dietary saturated by unsaturated fatty acids: effects of platelet protein kinase C activity, urinary content of 2,3-dinor-TXB2 and in vitro platelet aggregation in healthy man. Turpeinen, A.M., Pajari, A.M., Freese, R., Sauer, R., Mutanen, M. Thromb. Haemost. (1998) [Pubmed]
  8. Increased thromboxane metabolites excretion in liver cirrhosis. Davì, G., Ferro, D., Basili, S., Iuliano, L., Camastra, C., Giammarresi, C., Santarone, S., Rocca, B., Landolfi, R., Ciabattoni, G., Cordova, C., Violi, F. Thromb. Haemost. (1998) [Pubmed]
  9. Chronic dietary supplementation with L-arginine inhibits platelet aggregation and thromboxane A2 synthesis in hypercholesterolaemic rabbits in vivo. Bode-Böger, S.M., Böger, R.H., Kienke, S., Böhme, M., Phivthong-ngam, L., Tsikas, D., Frölich, J.C. Cardiovasc. Res. (1998) [Pubmed]
  10. Reduced prostacyclin to thromboxane A2 ratio is correlated with central apneas in preterm infants. Hoch, B., Bernhard, M. Prostaglandins Other Lipid Mediat. (1999) [Pubmed]
  11. Increased urinary excretion of thromboxane B2 and 2,3-dinor-TxB2 in cyclosporin A nephrotoxicity. Benigni, A., Chiabrando, C., Piccinelli, A., Perico, N., Gavinelli, M., Furci, L., Patino, O., Abbate, M., Bertani, T., Remuzzi, G. Kidney Int. (1988) [Pubmed]
  12. Effect of captopril on prostacyclin and nitric oxide formation in healthy human subjects: interaction with low dose acetylsalicylic acid. Böger, R.H., Bode-Böger, S.M., Kramme, P., Tsikas, D., Gutzki, F.M., Frölich, J.C. British journal of clinical pharmacology. (1996) [Pubmed]
  13. Evaluation of plasma 11-dehydro-thromboxane B2 as an indicator for thromboxane A2 synthesis in vivo in laboratory animals. Kawamura, M., Harada, Y., Katori, M. Thromb. Res. (1995) [Pubmed]
  14. Influence of morphology and malignancy of three new human melanoma cell lines on the cyclooxygenase pathway. Malle, E., Rotheneder, M., Vetterlein, M., Kostner, G.M. Prostaglandins (1989) [Pubmed]
  15. Thromboxane B2 urinary metabolites in patients undergoing cardiopulmonary bypass. Jörres, A., Chiabrando, C., Kordonouri, O., Schiessler, A., Hess, S., Farke, S., Gahl, G.M., Müller, C., Rivoltella, L., Djurup, R. Eicosanoids (1992) [Pubmed]
  16. Interaction of a thrombin inhibitor and a platelet GP IIb/IIIa antagonist in vivo: evidence that thrombin mediates platelet aggregation and subsequent thromboxane A2 formation during coronary thrombolysis. Pratico, D., Murphy, N.P., Fitzgerald, D.J. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  17. Increased prostacyclin production during exercise in untrained and trained men: effect of low-dose aspirin. Böger, R.H., Bode-Böger, S.M., Schröder, E.P., Tsikas, D., Frölich, J.C. J. Appl. Physiol. (1995) [Pubmed]
  18. Differential inhibition of human platelet aggregation and thromboxane A2 formation by L-arginine in vivo and in vitro. Bode-Böger, S.M., Böger, R.H., Galland, A., Frölich, J.C. Naunyn Schmiedebergs Arch. Pharmacol. (1998) [Pubmed]
  19. Measurement of canine urinary thromboxanes by GC-MS and HPLC-RIA. Tagari, P., Callaghan, D.H., Black, C., Yerge, J.A. Prostaglandins (1994) [Pubmed]
  20. Improvement of vascular function by chronic administration of a cyclo-oxygenase inhibitor in cholesterol-fed rabbits. Srisawat, S., Phivthong-Ngam, L., Unchern, S., Chantharaksri, U., Govitrapong, P., Sanvarinda, Y. Clin. Exp. Pharmacol. Physiol. (2003) [Pubmed]
  21. Cyclooxygenase isoforms and platelet vessel wall interactions in the apolipoprotein E knockout mouse model of atherosclerosis. Belton, O.A., Duffy, A., Toomey, S., Fitzgerald, D.J. Circulation (2003) [Pubmed]
  22. The role of thromboxane and prostacyclin in ciclosporin-induced nephrotoxicity. Heering, P., Strobach, H., Schrör, K., Grabensee, B. Nephron (1992) [Pubmed]
  23. Excretion of primary prostanoids and their metabolites during acute volume expansion. Seyberth, H.W., Tulassay, T., Kühl, P.G., Soeding, K., Rascher, W., Schweer, H. Prostaglandins (1988) [Pubmed]
  24. Measurement of prostaglandins, thromboxanes and hydroxy fatty acids by stable isotope dilution gas chromatography/mass spectrometry. Leis, H.J., Hohenester, E., Gleispach, H., Malle, E., Mayer, B. Biomed. Environ. Mass Spectrom. (1987) [Pubmed]
  25. Effects of a selective thromboxane receptor antagonist (GR32191B) and of glyceryl trinitrate on bleeding time in man. Ritter, J.M., Benjamin, N., Doktor, H.S., Barrow, S.E., Mant, T.G., Schey, S., Stewart-Long, P. British journal of clinical pharmacology. (1990) [Pubmed]
  26. Prostanoid excretion before in vitro fertilization relates to the likelihood of pregnancy. van der Weiden, R.M., Helmerhorst, F.M., Keirse, M.J. Prostaglandins Leukot. Essent. Fatty Acids (1995) [Pubmed]
  27. Effects of naproxen on the in vivo synthesis of thromboxane and prostacyclin in man. Vesterqvist, O., Gréen, K. Eur. J. Clin. Pharmacol. (1989) [Pubmed]
  28. Urinary excretion of 2,3-dinor-thromboxane B1, a major metabolite of thromboxane B2 in the rat. Chiabrando, C., Corada, M., Bachi, A., Fanelli, R. Prostaglandins (1994) [Pubmed]
  29. A chemiluminescent immunoassay for urinary thromboxane B2. Morello, A., Chang, S., Jacob, A., Law, S.J., Stastny, M., Martin, L., Pamidi, A., Kotake, A. Prostaglandins (1991) [Pubmed]
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