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Chemical Compound Review

Neuro_000201     (2- azanidylcyclohexyl)azanide;...

Synonyms: NSC-363811, NSC-363813, NSC-363814, NSC276017, NSC363811, ...
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Disease relevance of NSC363812


High impact information on NSC363812


Chemical compound and disease context of NSC363812


Biological context of NSC363812


Anatomical context of NSC363812

  • An unexpected biotransformation pathway for tetrachloro-(d,l-trans)-1,2-diaminocyclohexaneplatinum(IV) (tetraplatin) in the L1210 cell line [13].
  • Using six pairs of acquired cisplatin-resistant and parent human tumor cell lines (four ovarian, one testicular, and one cervical) JM216 exhibited non-cross-resistance (resistance factor of < 1.5) in three whereas tetraplatin exhibited partial or full cross-resistance in all six pairs [4].
  • Plasma and ascitic fluid from tumor-bearing mice demonstrated equivalent abilities to reduce tetraplatin rapidly [16].
  • Only DDTC was moderately effective in preventing tetraplatin-induced decreases in platelet and lymphocyte counts [12].
  • Cisplatin had little effect on the excretion rates of the brush border enzymes alkaline phosphatase and maltase, whereas tetraplatin caused an initial elevation with delayed onset of peak excretion rates at 8 days postinjection [17].

Associations of NSC363812 with other chemical compounds

  • The in vitro cellular uptake of platinum by L1210 cells at 37 degrees C was about 4-fold higher after exposure to tetraplatin compared to cisplatin following a 2-h incubation at the two concentrations examined (2.5 and 5 micrograms/ml) [3].
  • The marked similarity in cytotoxicity between oxaliplatin and tetraplatin may be due to the formation of (trans-1,2-diaminocyclohexane)dichloroplatinum(II) in tissue culture media [5].
  • However, depletion of glutathione by buthionine 1-sulphoximine sensitizes all cell lines to the effects of cisDDP, chip and tetraplatin [d,1-trans-tetrachloro-1,2-diamino-cyclohexanplatinum (IV)] [18].
  • A 158-base-pair double-stranded DNA fragment, derived from pBR322 plasmid DNA, was modified by either CDDP, tetrachloro(dl-trans)-1,2-diaminocyclohexaneplatinum(IV) (tetraplatin) or trans-DDP (the stereoisomer of CDDP and clinically ineffective) [19].
  • Synthesis, physical properties, and antitumor activity of tetraplatin and related tetrachloroplatinum(IV) stereoisomers of 1,2-diaminocyclohexane [20].

Gene context of NSC363812

  • Tetraplatin and lobaplatin showed, respectively, partial and complete cross-resistance in GLC4/CDDP but no cross-resistance in Tera-CP [21].
  • At an optimal dose of 5.7 mg/kg/injection given as a single dose on days 1, 5, and 9, tetraplatin increased the median life span over controls by more than 566% with 5 of 8 long-term (50-day) survivors [3].
  • Only one of the six parent tumour lines (PXN/100) was markedly sensitive to tetraplatin [22].
  • Intracellular accumulations of tetraplatin in both L1210/0 and L1210/DDP cells were increased by GSH, whereas in L1210/DACH cells platinum uptake decreased in the presence of the thiol [10].
  • Inhibition of brain choline acetyltransferase by tetraplatin [23].

Analytical, diagnostic and therapeutic context of NSC363812


  1. In vitro biotransformations of tetrachloro(d,l-trans)-1,2-diaminocyclohexaneplatinum(IV) (tetraplatin) in rat plasma. Chaney, S.G., Wyrick, S., Till, G.K. Cancer Res. (1990) [Pubmed]
  2. Comparison of cellular accumulation and cytotoxicity of cisplatin with that of tetraplatin and amminedibutyratodichloro(cyclohexylamine)platinum(IV) (JM221) in human ovarian carcinoma cell lines. Mistry, P., Kelland, L.R., Loh, S.Y., Abel, G., Murrer, B.A., Harrap, K.R. Cancer Res. (1992) [Pubmed]
  3. Therapeutic and pharmacological studies of tetrachloro(d,l-trans)1,2-diaminocyclohexane platinum (IV) (tetraplatin), a new platinum analogue. Rahman, A., Roh, J.K., Wolpert-DeFilippes, M.K., Goldin, A., Venditti, J.M., Woolley, P.V. Cancer Res. (1988) [Pubmed]
  4. Preclinical antitumor evaluation of bis-acetato-ammine-dichloro-cyclohexylamine platinum(IV): an orally active platinum drug. Kelland, L.R., Abel, G., McKeage, M.J., Jones, M., Goddard, P.M., Valenti, M., Murrer, B.A., Harrap, K.R. Cancer Res. (1993) [Pubmed]
  5. In vitro cytotoxicity, protein binding, red blood cell partitioning, and biotransformation of oxaliplatin. Pendyala, L., Creaven, P.J. Cancer Res. (1993) [Pubmed]
  6. Biochemical pharmacology of homologous alicyclic mixed amine platinum(II) complexes in sensitive and resistant tumor cell lines. Yoshida, M., Khokhar, A.R., Siddik, Z.H. Cancer Res. (1994) [Pubmed]
  7. Lack of neurotoxicity of oral bisacetatoamminedichlorocyclohexylamine-platinum(IV) in comparison to cisplatin and tetraplatin in the rat. McKeage, M.J., Boxall, F.E., Jones, M., Harrap, K.R. Cancer Res. (1994) [Pubmed]
  8. Role of carrier ligand in platinum resistance of human carcinoma cell lines. Schmidt, W., Chaney, S.G. Cancer Res. (1993) [Pubmed]
  9. Circumvention of acquired tetraplatin resistance in a human ovarian carcinoma cell line by a novel trans platinum complex, JM335 [trans ammine (cyclohexylamine) dichloro dihydroxo platinum (IV)]. Mellish, K.J., Barnard, C.F., Kelland, L.R., Harrap, K.R. Int. J. Cancer (1994) [Pubmed]
  10. Glutathione-mediated modulation of tetraplatin activity against sensitive and resistant tumor cells. Kido, Y., Khokhar, A.R., Siddik, Z.H. Biochem. Pharmacol. (1994) [Pubmed]
  11. In vitro platinum drug chemosensitivity of human cervical squamous cell carcinoma cell lines with intrinsic and acquired resistance to cisplatin. Mellish, K.J., Kelland, L.R., Harrap, K.R. Br. J. Cancer (1993) [Pubmed]
  12. Reduction of tetrachloro(dl-trans)1,2-diaminocyclohexaneplatinum(IV) (tetraplatin) toxicity by the administration of diethyldithiocarbamate (DDTC), S-2(3-aminopropylamino)ethylphosphorothioic acid (WR-2721), or sodium selenite in the Fischer 344 rat. Carfagna, P.F., Chaney, S.G., Chang, J., Holbrook, D.J. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1990) [Pubmed]
  13. An unexpected biotransformation pathway for tetrachloro-(d,l-trans)-1,2-diaminocyclohexaneplatinum(IV) (tetraplatin) in the L1210 cell line. Chaney, S.G., Gibbons, G.R., Wyrick, S.D., Podhasky, P. Cancer Res. (1991) [Pubmed]
  14. The relationships between glutathione, glutathione-S-transferase and cytotoxicity of platinum drugs and melphalan in eight human ovarian carcinoma cell lines. Mistry, P., Kelland, L.R., Abel, G., Sidhar, S., Harrap, K.R. Br. J. Cancer (1991) [Pubmed]
  15. Pharmacokinetics of intravenously injected [3H]tetrachloro(D,L-trans)1,2-diaminocyclohexane platinum (IV) (tetraplatin) in mice. Kido, Y., Khokhar, A.R., Siddik, Z.H. Drug Metab. Dispos. (1992) [Pubmed]
  16. Pharmacokinetics of tetraplatin administered intraperitoneally with reduced glutathione in mice. Kido, Y., Khokhar, A.R., Yoshida, M., Thai, G.W., Siddik, Z.H. Drug Metab. Dispos. (1994) [Pubmed]
  17. In vivo biochemical indices of nephrotoxicity of platinum analogs tetraplatin, CHIP, and cisplatin in the Fischer 344 rat. Smith, M.A., Smith, J.H., Litterst, C.L., Copley, M.P., Uozumi, J., Boyd, M.R. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1988) [Pubmed]
  18. The role of metallothionein, glutathione, glutathione S-transferases and DNA repair in resistance to platinum drugs in a series of L1210 cell lines made resistant to anticancer platinum agents. Hrubisko, M., McGown, A.T., Fox, B.W. Biochem. Pharmacol. (1993) [Pubmed]
  19. Detection of proteins that recognize platinum-modified DNA using gel mobility shift assay. Fujiwara, Y., Kasahara, K., Sugimoto, Y., Nishio, K., Ohmori, T., Saijo, N. Jpn. J. Cancer Res. (1990) [Pubmed]
  20. Synthesis, physical properties, and antitumor activity of tetraplatin and related tetrachloroplatinum(IV) stereoisomers of 1,2-diaminocyclohexane. Anderson, W.K., Quagliato, D.A., Haugwitz, R.D., Narayanan, V.L., Wolpert-DeFilippes, M.K. Cancer treatment reports. (1986) [Pubmed]
  21. Relationship of cellular glutathione to the cytotoxicity and resistance of seven platinum compounds. Meijer, C., Mulder, N.H., Timmer-Bosscha, H., Sluiter, W.J., Meersma, G.J., de Vries, E.G. Cancer Res. (1992) [Pubmed]
  22. Acquisition of platinum drug resistance and platinum cross resistance patterns in a panel of human ovarian carcinoma xenografts. Jones, M., Siracky, J., Kelland, L.R., Harrap, K.R. Br. J. Cancer (1993) [Pubmed]
  23. Inhibition of brain choline acetyltransferase by tetraplatin. Ho, B.T., Feiffer, R., Tansey, L.W., Newman, R.A., Fields, W.S., Krakoff, I.H. Brain Res. Bull. (1987) [Pubmed]
  24. Ormaplatin resistance is associated with decreased accumulation of its platinum (II) analogue, dichloro(D,L-trans)1,2-diaminocyclohexaneplatinum (II). Rischin, D., Ling, V. Br. J. Cancer (1996) [Pubmed]
  25. Interaction of D,L- and D-tetraplatin with hyperthermia in vitro and in vivo. Epelbaum, R., Teicher, B.A., Holden, S.A., Ara, G., Varshney, A., Herman, T.S. Eur. J. Cancer (1992) [Pubmed]
  26. Comparative nephrotoxicity of tetraplatin and cisplatin in rats. Rahman, A., Roh, J.K., Preuss, H.G. Nephron (1993) [Pubmed]
  27. The role of glutathione (GSH) in determining sensitivity to platinum drugs in vivo in platinum-sensitive and -resistant murine leukaemia and plasmacytoma and human ovarian carcinoma xenografts. Goddard, P., Valenti, M., Kelland, L.R. Anticancer Res. (1994) [Pubmed]
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