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Chemical Compound Review

carbacyclin     (5E)-5-[(3aS,4S,5R,6aR)-5- hydroxy-4-[(E...

Synonyms: Carbacycline, Carba pgx, CHEMBL435828, SureCN1479163, BSPBio_001573, ...
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Disease relevance of carbacyclin


High impact information on carbacyclin


Chemical compound and disease context of carbacyclin


Biological context of carbacyclin

  • Carbacyclin derivative E/Z-2d was found to be essentially inactive as an inhibitor of ADP induced human platelet aggregation, having an IC50 of >10 micromol/L [13].
  • These results emphasize the adipogenic, nonmitogenic role of cPGI2 and also allow the distinction between the various adipogenic/mitogenic factors which affect adipose cell differentiation [14].
  • However, treatment of intact platelets with phorbol 12-myristate 13-acetate, thrombin or carbacyclin did not increase PS-p68 phosphorylation [15].
  • In contrast, carbaprostacyclin (cPGI2), a stable analogue of prostacyclin, behaves as a true adipogenic factor leading to a 4 to 5-fold increase in GPDH-specific activities with no significant effect on cell growth [14].
  • Intra-arterial 9-beta-methyl carbacyclin improved early PTFE graft patency and inhibited platelet deposition in a severe canine model, independent of baseline platelet aggregation status, which also had an important effect on graft patency [16].

Anatomical context of carbacyclin


Associations of carbacyclin with other chemical compounds


Gene context of carbacyclin


Analytical, diagnostic and therapeutic context of carbacyclin

  • A subcutaneous infusion pump was used to deliver either saline solution (control) or 9-beta-methyl carbacyclin (Ciprostine) at 100 (CARB-100) or 200 ng/kg/min (CARB-200) through a femoral artery branch just proximal to one of the femoral grafts, with the contralateral graft serving as a noninfused control [16].
  • A chemically stable prostacyclin analogue (PGI2-A, carbacyclin, OP-41483) was evaluated as an adjunct to potassium cardioplegia in infants (n = 13) and children (n = 32), in whom the current potassium cardioplegia may be limited in its effects [29].
  • 2) With oral administration to guinea pigs, OP-41483 given as its alpha-cyclodextrin clathrate (OP-41483 alpha-CD) inhibited platelet adhesiveness at doses higher than 1.0 mg/kg (expressed in terms of OP-41483), whereas PGl2 and carbacyclin did not at 10 mg/kg [30].
  • Extracts of both fetal and maternal effluents from placenta perfused with carbacyclin contained a component which on reverse phase HPLC appeared less polar than carbacyclin [31].


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  7. Inhibition of inositol 1,4,5-trisphosphate-induced Ca2+ release by cAMP-dependent protein kinase in a living cell. Tertyshnikova, S., Fein, A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  8. Stromal production of prostacyclin confers an antiapoptotic effect to colonic epithelial cells. Cutler, N.S., Graves-Deal, R., LaFleur, B.J., Gao, Z., Boman, B.M., Whitehead, R.H., Terry, E., Morrow, J.D., Coffey, R.J. Cancer Res. (2003) [Pubmed]
  9. Synthetic Prostacyclin Analogs Differentially Regulate Macrophage Function via Distinct Analog-Receptor Binding Specificities. Aronoff, D.M., Peres, C.M., Serezani, C.H., Ballinger, M.N., Carstens, J.K., Coleman, N., Moore, B.B., Peebles, R.S., Faccioli, L.H., Peters-Golden, M. J. Immunol. (2007) [Pubmed]
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  12. Prostaglandin F2 alpha induces cardiac myocyte hypertrophy in vitro and cardiac growth in vivo. Lai, J., Jin, H., Yang, R., Winer, J., Li, W., Yen, R., King, K.L., Zeigler, F., Ko, A., Cheng, J., Bunting, S., Paoni, N.F. Am. J. Physiol. (1996) [Pubmed]
  13. A new strategy for the enantioselective synthesis of carba-prostacyclin analogues based on organocopper conjugate addition to a bicyclic azoene and its application to the synthesis of 13,14-dinor-inter-p-phenylene carbacyclin. van Bergen, M., Gais, H.J. J. Am. Chem. Soc. (2002) [Pubmed]
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  16. Intraarterial 9-beta-methyl carbacyclin improves canine polytetrafluoroethylene graft patency. Dacey, L.J., Hees, P.S., Cronenwett, J.L. J. Vasc. Surg. (1988) [Pubmed]
  17. Interleukin 1beta induces type II-secreted phospholipase A(2) gene in vascular smooth muscle cells by a nuclear factor kappaB and peroxisome proliferator-activated receptor-mediated process. Couturier, C., Brouillet, A., Couriaud, C., Koumanov, K., Béréziat, G., Andréani, M. J. Biol. Chem. (1999) [Pubmed]
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  19. The prostacyclin analogue carbacyclin inhibits Ca(2+)-activated K+ current in aortic baroreceptor neurones of rats. Li, Z., Lee, H.C., Bielefeldt, K., Chapleau, M.W., Abboud, F.M. J. Physiol. (Lond.) (1997) [Pubmed]
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  27. Cyclooxygenase-1 and -2 knockout mice demonstrate increased cardiac ischemia/reperfusion injury but are protected by acute preconditioning. Camitta, M.G., Gabel, S.A., Chulada, P., Bradbury, J.A., Langenbach, R., Zeldin, D.C., Murphy, E. Circulation (2001) [Pubmed]
  28. Role of extracellular cysteine residues in dimerization/oligomerization of the human prostacyclin receptor. Giguère, V., Gallant, M.A., de Brum-Fernandes, A.J., Parent, J.L. Eur. J. Pharmacol. (2004) [Pubmed]
  29. Evaluation of prostacyclin analogue OP-41483 as an adjunct to crystalloid cardioplegia in infants and children. Matsuda, H., Sawa, Y., Kuki, S., Nomura, F., Ohtani, M., Takami, H., Shirakura, R., Nakano, S., Kawashima, Y. Ann. Thorac. Surg. (1989) [Pubmed]
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