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Chemical Compound Review

Dimesnum     disodium2-(2- sulfonatoethyldisulfanyl) eth...

Synonyms: Tavocept, Dimesna, Dimesna [INN], CCRIS 5852, CHEMBL2104318, ...
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Disease relevance of coenzyme M

  • The ratio of the urinary excretion of the uroprotectant mesna (active form) to dimesna (inactive form) correlated with the degree of renal toxicity [1].
  • The relationship between and urinary excretion of mesna and dimesna also was examined by comparing the data obtained in patients who developed hemorrhagic cystitis versus those who did not [2].
  • The cumulative urinary excretion of IF, 4-OH-IF, 3-DCE-IF, 2-DCE-IF, mesna, and its disulfide dimesna was studied in 11 patients with bronchogenic carcinoma receiving IF on a 5-day divided-dose schedule (1.5 g/m2 daily) with concomitant application of mesna (0.3 g/m2 at 0,4, and 8 h after IF infusion) [3].
 

High impact information on coenzyme M

  • The ratio of mesna:dimesna was higher in protein-free plasma than it was in the urine, which suggested that most urinary mesna is produced by glomerular filtration of mesna rather than by renal tubular reduction of dimesna [4].
  • The sum of mesna and dimesna excretion after the i.v. doses (73% of the dose) and the four oral formulations (68-73%) showed no difference in urinary bioavailability, consistent with the blood data [4].
  • Pharmacokinetics of mesna and dimesna after simultaneous intravenous bolus and infusion administration in patients undergoing bone marrow transplantation [2].
  • This was not the case with dimesna, in which patients with hemorrhagic cystitis excreted in urine less than 50% of the amount of dimesna excreted by those without hemorrhagic cystitis [2].
  • The mean +/-SD values of t1/2 and MRT of dimesna were 1.29 +/- 0.6 hours and 6.68 +/- 1.05 hours, respectively, and the ratio of the area under the concentration-time curve (AUC) of mesna to that of dimesna was 1.21 +/- 0.57 [2].
 

Chemical compound and disease context of coenzyme M

  • BioNumerik Pharmacology Inc, Baxter Oncology GmbH (formerly ASTA Medica AG) and Grelan Pharmaceutical Co Ltd are developing BNP-7787 for the potential reduction of toxicity associated with cisplatin and carboplatin treatment in cancer patients [5].
 

Biological context of coenzyme M

 

Anatomical context of coenzyme M

 

Associations of coenzyme M with other chemical compounds

 

Gene context of coenzyme M

 

Analytical, diagnostic and therapeutic context of coenzyme M

  • In single-pass perfusions, each liver was perfused with up to three dimesna concentrations during consecutive 20-min periods [15].
  • Following single oral administration of 20 or 40 mg/kg mesna, 52.4% and 52.6%, respectively, of the dose were excreted in the urine as reactive thiol groups, the remainder as mesna disulfide (dimesna), the only metabolite of mesna; after i.v. injection of 20 mg/kg mesna, 48.7% of the dose administered appeared as thiol groups in the urine [16].

References

  1. Urinary proton magnetic resonance studies of early ifosfamide-induced nephrotoxicity and encephalopathy. Foxall, P.J., Singer, J.M., Hartley, J.M., Neild, G.H., Lapsley, M., Nicholson, J.K., Souhami, R.L. Clin. Cancer Res. (1997) [Pubmed]
  2. Pharmacokinetics of mesna and dimesna after simultaneous intravenous bolus and infusion administration in patients undergoing bone marrow transplantation. el-Yazigi, A., Ernst, P., al-Rawithi, S., Legayada, E., Raines, D.A. Journal of clinical pharmacology. (1997) [Pubmed]
  3. Urinary excretion of ifosfamide, 4-hydroxyifosfamide, 3- and 2-dechloroethylifosfamide, mesna, and dimesna in patients on fractionated intravenous ifosfamide and concomitant mesna therapy. Kurowski, V., Wagner, T. Cancer Chemother. Pharmacol. (1997) [Pubmed]
  4. Similar bioavailability of single-dose oral and intravenous mesna in the blood and urine of healthy human subjects. Goren, M.P., Houle, J.M., Bush, D.A., Li, J.T., Newman, C.E., Brade, W.P. Clin. Cancer Res. (1998) [Pubmed]
  5. BNP-7787 (BioNumerik/Baxter Oncology/Grelan). Reilly, R.T. IDrugs : the investigational drugs journal. (2004) [Pubmed]
  6. Oral bioavailability of mesna tablets. Stofer-Vogel, B., Cerny, T., Borner, M., Lauterburg, B.H. Cancer Chemother. Pharmacol. (1993) [Pubmed]
  7. Pharmacokinetics of intravenous and oral sodium 2-mercaptoethane sulphonate (mesna) in normal subjects. James, C.A., Mant, T.G., Rogers, H.J. British journal of clinical pharmacology. (1987) [Pubmed]
  8. Inhibition of rat hepatic microsomal lipid peroxidation by mesna via glutathione. Bast, A., Haenen, G.R., Savenije-Chapel, E.M. Arzneimittel-Forschung. (1987) [Pubmed]
  9. Liquid chromatographic analysis of mesna and dimesna in plasma and urine of patients treated with mesna. el-Yazigi, A., Yusuf, A., al-Rawithi, S. Therapeutic drug monitoring. (1995) [Pubmed]
  10. Antitumor activity of 2-mercaptoethanesulfonate (mesna) in vitro. Its potential use in the treatment of superficial bladder cancer. Blomgren, H., Hallström, M., Hillgren, H. Anticancer Res. (1991) [Pubmed]
  11. Dithio-bis-mercaptoethanesulphonate (DIMESNA) does not prevent cellular damage by metabolites of ifosfamide and cyclophosphamide in LLC-PK1 cells. Mohrmann, M., Ansorge, S., Schönfeld, B., Brandis, M. Pediatr. Nephrol. (1994) [Pubmed]
  12. The interactions of mesna and dimesna with the sulfate exchange in human red blood cells. Reuther, H., Kohl, M., Wildenauer, D.B. Arzneimittel-Forschung. (1986) [Pubmed]
  13. Prevention of urinary bladder tumors in cyclophosphamide-treated rats by additional medication with the uroprotectors sodium 2-mercaptoethane sulfonate (mesna) and disodium 2,2'-dithio-bis-ethane sulfonate (dimesna). Habs, M.R., Schmähl, D. Cancer (1983) [Pubmed]
  14. Ifosfamide and mesna. Schoenike, S.E., Dana, W.J. Clinical pharmacy. (1990) [Pubmed]
  15. Reduction of dimesna to mesna by the isolated perfused rat liver. Goren, M.P., Hsu, L.C., Li, J.T. Cancer Res. (1998) [Pubmed]
  16. Bioavailability of orally administered mesna. Burkert, H., Lücker, P.W., Wetzelsberger, N., Breuel, H.P. Arzneimittel-Forschung. (1984) [Pubmed]
 
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