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Chemical Compound Review

Didie     2-cyanoguanidine

Synonyms: Dicy, Dicyandiamin, dicyandiamie, Dicyandiamide, Dicyandiamido, ...
 
 
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Disease relevance of Dicyandiamide

 

High impact information on Dicyandiamide

  • CHS 828, a novel pyridyl cyanoguanidine with potent antitumor activity in vitro and in vivo [6].
  • In competition experiments using [3H]glibenclamide as radioligand, SUR1(T1285L, M1289T) showed much higher affinity toward the cyanoguanidine openers pinacidil and P1075 than SUR1 wild type [7].
  • It also highlights that small structural changes can dramatically shift the efficacy of the cyanoguanidine type of selective activators of Kir6.2/SUR2 potassium channels [8].
  • Condensation of appropriately substituted (arylmethyl)triphenylphosphoranes with 4, 4-ethylenedioxycyclohexanone, followed by hydrogenation (H2/Pd-C) and acidolysis, yielded the corresponding 4-(arylmethyl)cyclohexanones, which were then condensed with cyanoguanidine to form the tetrahydroquinazolines [9].
  • Structure-activity relationships for the cyanoguanidine portion of the lead cardiac selective ATP-sensitive potassium channel (KATP) opener (3) are described [10].
 

Biological context of Dicyandiamide

 

Anatomical context of Dicyandiamide

  • CONCLUSIONS: A comparison with previously published data obtained in isolated middle cerebral and basilar arteries showed that potassium channel openers of the benzopyrane and cyanoguanidine type are much more potent in pial arteries than in peripheral arteries in situ or in isolated arteries of the circle of Willis and of peripheral vascular beds [16].
  • The rank order of potency of a series of benzopyran and cyanoguanidine K+ channel openers (KCOs) for causing relaxation of the PGF2 alpha-precontracted porcine coronary artery was determined [17].
  • In this study 2-guanidine-4-methylquinazoline (2-GMQ) appeared to decrease basal and stimulated gastric acid secretion, while structurally related compounds as dimethyl-biguanide, cyanoguanidine and 2-cyanoamino-4-methylpyrymidine did not [18].
  • Such patients should have periodic white blood cell counts because substituting the cyanoguanidine group for the thiourea group may not eliminate the hematologic effects of the H2 receptor antagonists [19].
 

Associations of Dicyandiamide with other chemical compounds

 

Gene context of Dicyandiamide

 

Analytical, diagnostic and therapeutic context of Dicyandiamide

References

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  2. Modulation of pyridyl cyanoguanidine (CHS 828) induced cytotoxicity by 3-aminobenzamide in U-937 GTB cells. Lövborg, H., Martinsson, P., Gullbo, J., Ekelund, S., Nygren, P., Larsson, R. Biochem. Pharmacol. (2002) [Pubmed]
  3. Use of fourier transform infrared spectroscopy to follow the heterocumulene aided thermal dehydration of phthalic and naphthalic acids. Rigout, M.L., Lewis, D.M. Applied spectroscopy (2006) [Pubmed]
  4. Electrophysiologic effects of a potassium channel activator (pinacidil) on repolarization parameters in healthy volunteers: a surface ECG study. Nony, P., Girard, P., Arnaud, P., Rubel, P., Fayn, J., de Breyne, B., Haugh, M.C., Girard, I., Ferry, S., Boissel, J.P. J. Cardiovasc. Pharmacol. (1993) [Pubmed]
  5. Cytotoxic effect in vivo and in vitro of CHS 828 on human myeloma cell lines. Hovstadius, P., Lindhagen, E., Hassan, S., Nilsson, K., Jernberg-Wiklund, H., Nygren, P., Binderup, L., Larsson, R. Anticancer Drugs (2004) [Pubmed]
  6. CHS 828, a novel pyridyl cyanoguanidine with potent antitumor activity in vitro and in vivo. Hjarnaa, P.J., Jonsson, E., Latini, S., Dhar, S., Larsson, R., Bramm, E., Skov, T., Binderup, L. Cancer Res. (1999) [Pubmed]
  7. Effect of two amino acids in TM17 of Sulfonylurea receptor SUR1 on the binding of ATP-sensitive K+ channel modulators. Hambrock, A., Kayar, T., Stumpp, D., Osswald, H. Diabetes (2004) [Pubmed]
  8. Arylcyanoguanidines as activators of Kir6.2/SUR1K ATP channels and inhibitors of insulin release. Tagmose, T.M., Schou, S.C., Mogensen, J.P., Nielsen, F.E., Arkhammar, P.O., Wahl, P., Hansen, B.S., Worsaae, A., Boonen, H.C., Antoine, M.H., Lebrun, P., Hansen, J.B. J. Med. Chem. (2004) [Pubmed]
  9. Synthesis and antiparasitic and antitumor activity of 2, 4-diamino-6-(arylmethyl)-5,6,7,8-tetrahydroquinazoline analogues of piritrexim. Rosowsky, A., Papoulis, A.T., Forsch, R.A., Queener, S.F. J. Med. Chem. (1999) [Pubmed]
  10. Cardioselective anti-ischemic ATP-sensitive potassium channel openers. 3. Structure-activity studies on benzopyranyl cyanoguanidines: modification of the cyanoguanidine portion. Atwal, K.S., Grover, G.J., Ahmed, S.Z., Sleph, P.G., Dzwonczyk, S., Baird, A.J., Normandin, D.E. J. Med. Chem. (1995) [Pubmed]
  11. Cyanoguanidine-thiourea equivalence in the development of the histamine H2-receptor antagonist, cimetidine. Durant, G.J., Emmett, J.C., Ganellin, C.R., Miles, P.D., Parsons, M.E., Prain, H.D., White, G.R. J. Med. Chem. (1977) [Pubmed]
  12. Pharmacological characterization of a 1,4-dihydropyridine analogue, 9-(3,4-dichlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (A-184209) as a novelK(ATP) channel inhibitor. Gopalakrishnan, M., Miller, T.R., Buckner, S.A., Milicic, I., Molinari, E.J., Whiteaker, K.L., Davis-Taber, R., Scott, V.E., Cassidy, C., Sullivan, J.P., Carroll, W.A. Br. J. Pharmacol. (2003) [Pubmed]
  13. Bioavailability and anticonvulsant activity of 2-cyanoguanidinophenytoin, a structural analogue of phenytoin. Lambert, D.M., Masereel, B., Gallez, B., Geurts, M., Scriba, G.K. Journal of pharmaceutical sciences. (1996) [Pubmed]
  14. A hollow fiber model for in vitro studies of cytotoxic compounds: activity of the cyanoguanidine CHS 828. Hassan, S.B., de la Torre, M., Nygren, P., Karlsson, M.O., Larsson, R., Jonsson, E. Anticancer Drugs (2001) [Pubmed]
  15. Development and characterization of two human tumor sublines expressing high-grade resistance to the cyanoguanidine CHS 828. Gullbo, J., Lövborg, H., Dhar, S., Lukinius, A., Oberg, F., Nilsson, K., Björkling, F., Binderup, L., Nygren, P., Larsson, R. Anticancer Drugs (2004) [Pubmed]
  16. Dilating effect of perivascularly applied potassium channel openers cromakalim and pinacidil in rat and cat pial arteries in situ. Wahl, M., Parsons, A.A., Schilling, L. Cardiovasc. Res. (1994) [Pubmed]
  17. Evidence that BKCa channel activation contributes to K+ channel opener induced relaxation of the porcine coronary artery. Balwierczak, J.L., Krulan, C.M., Kim, H.S., DelGrande, D., Weiss, G.B., Hu, S. Naunyn Schmiedebergs Arch. Pharmacol. (1995) [Pubmed]
  18. Effects of 2-guanidine-4-methylquinazoline on gastric acid secretion in rats. Pinelli, A., Trivulzio, S., Pojaga, G., Rossoni, G. Pharmacol. Res. (1996) [Pubmed]
  19. Prolonged WBC depression after cimetidine in a patient with chronic myelogenous leukemia. Linhardt, G.E., Gadacz, T.R. South. Med. J. (1981) [Pubmed]
  20. Chemistry of aminoiminomethanesulfinic and -sulfonic acids related to the toxicity of thioureas. Miller, A.E., Bischoff, J.J., Pae, K. Chem. Res. Toxicol. (1988) [Pubmed]
  21. A possible mechanism of action of a new potassium channel opener, AL0671, on lipid metabolism in obese Zucker rats. Matzno, S., Gohda, M., Eda, M., Ebisu, H., Uno, S., Ishida, N., Nakamura, N., Yamanouchi, K. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  22. Interaction of a novel dihydropyridine K+ channel opener, A-312110, with recombinant sulphonylurea receptors and KATP channels: comparison with the cyanoguanidine P1075. Felsch, H., Lange, U., Hambrock, A., Löffler-Walz, C., Russ, U., Carroll, W.A., Gopalakrishnan, M., Quast, U. Br. J. Pharmacol. (2004) [Pubmed]
  23. Identification of 4-piperazin-1-yl-quinazoline template based aryl and benzyl thioureas as potent, selective, and orally bioavailable inhibitors of platelet-derived growth factor (PDGF) receptor. Heath, J.A., Mehrotra, M.M., Chi, S., Yu, J.C., Hutchaleelaha, A., Hollenbach, S.J., Giese, N.A., Scarborough, R.M., Pandey, A. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  24. Human beta3 adrenergic receptor agonists containing cyanoguanidine and nitroethylenediamine moieties. Brockunier, L.L., Candelore, M.R., Cascieri, M.A., Liu, Y., Tota, L., Wyvratt, M.J., Fisher, M.H., Weber, A.E., Parmee, E.R. Bioorg. Med. Chem. Lett. (2001) [Pubmed]
  25. Lack of carcinogenicity of cyanoguanidine in F344 rats. Yasuhara, K., Shimo, T., Mitsumori, K., Onodera, H., Kitaura, K., Takahashi, M. Food Chem. Toxicol. (1997) [Pubmed]
  26. Anticancer agent CHS 828 suppresses nuclear factor-kappa B activity in cancer cells through downregulation of IKK activity. Olsen, L.S., Hjarnaa, P.J., Latini, S., Holm, P.K., Larsson, R., Bramm, E., Binderup, L., Madsen, M.W. Int. J. Cancer (2004) [Pubmed]
 
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