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Chemical Compound Review

Mucofluid     2-sulfanylethanesulfonic acid

Synonyms: Mistabronco, HS-CoM, coenzima M, coenzyme M, Coenzym M, ...
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Disease relevance of coenzyme M

  • In the present work, coenzyme M (2-mercaptoethanesulfonic acid), a compound previously found only in the methanogenic Archaea where it serves as a methyl group carrier and activator, has been identified as the thiol and central cofactor of aliphatic epoxide carboxylation in the Gram-negative bacterium Xanthobacter strain Py2 [1].
  • Mesna and hyperhydration were associated with minimal bladder toxicity [2].
  • PURPOSE: To compare the use of intravenous (IV) hydration plus either continuous bladder irrigation or mesna for the prevention of hemorrhagic cystitis in the bone marrow transplant setting [3].
  • Ifosfamide with mesna uroprotection and etoposide: an effective regimen in the treatment of recurrent sarcomas and other tumors of children and young adults [4].
  • The incidence of consistent or severe hematuria was 33% in the mesna arm and 20% in the hyperhydration arm (P = .31) [5].

Psychiatry related information on coenzyme M


High impact information on coenzyme M


Chemical compound and disease context of coenzyme M


Biological context of coenzyme M


Anatomical context of coenzyme M


Associations of coenzyme M with other chemical compounds


Gene context of coenzyme M

  • Acrolein, an ALDH inhibitor, may be detoxified by conjugation with the nucleophilic thiol 2-mercaptoethanesulfonate (MESNA), which is released from MAF but not from 4-hpCPA [29].
  • Electrons for disulphide bond reduction are supplied from thioredoxin in the cytoplasm via DipZ in the membrane, but can be replaced by the chemical reductant, 2-mercaptoethanesulphonic acid [30].
  • To translate this process to human cancer therapy, we conducted a phase I trial of administration of a tissue plasminogen activator (tPA) with a free sulfhydryl donor (mesna) [31].
  • In vivo generation of angiostatin isoforms by administration of a plasminogen activator and a free sulfhydryl donor: a phase I study of an angiostatic cocktail of tissue plasminogen activator and mesna [31].
  • Incubation of construct 1 with 2-mercaptoethanesulfonic acid (MESNA) resulted in the MESNA thioester of R2 (1-353) (construct 2) [32].

Analytical, diagnostic and therapeutic context of coenzyme M


  1. A role for coenzyme M (2-mercaptoethanesulfonic acid) in a bacterial pathway of aliphatic epoxide carboxylation. Allen, J.R., Clark, D.D., Krum, J.G., Ensign, S.A. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  2. Ifosfamide is an active drug in Wilms' tumor: a phase II study conducted by the French Society of Pediatric Oncology. Tournade, M.F., Lemerle, J., Brunat-Mentigny, M., Bachelot, C., Roche, H., Taboureau, O., Olive, D., Lejars, O., Boilletot, A., Demeocq, F. J. Clin. Oncol. (1988) [Pubmed]
  3. Mesna compared with continuous bladder irrigation as uroprotection during high-dose chemotherapy and transplantation: a randomized trial. Vose, J.M., Reed, E.C., Pippert, G.C., Anderson, J.R., Bierman, P.J., Kessinger, A., Spinolo, J., Armitage, J.O. J. Clin. Oncol. (1993) [Pubmed]
  4. Ifosfamide with mesna uroprotection and etoposide: an effective regimen in the treatment of recurrent sarcomas and other tumors of children and young adults. Miser, J.S., Kinsella, T.J., Triche, T.J., Tsokos, M., Jarosinski, P., Forquer, R., Wesley, R., Magrath, I. J. Clin. Oncol. (1987) [Pubmed]
  5. Mesna versus hyperhydration for the prevention of cyclophosphamide-induced hemorrhagic cystitis in bone marrow transplantation. Shepherd, J.D., Pringle, L.E., Barnett, M.J., Klingemann, H.G., Reece, D.E., Phillips, G.L. J. Clin. Oncol. (1991) [Pubmed]
  6. Use of mesna to prevent ifosfamide-induced urotoxicity. Siu, L.L., Moore, M.J. Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer. (1998) [Pubmed]
  7. Structure-based perspectives on B12-dependent enzymes. Ludwig, M.L., Matthews, R.G. Annu. Rev. Biochem. (1997) [Pubmed]
  8. Mesna and bone-marrow transplantation. Becher, R., Kakati, S., Sandberg, A.A. N. Engl. J. Med. (1982) [Pubmed]
  9. Fatal hypokalaemia associated with ifosfamide/mesna chemotherapy. Husband, D.J., Watkin, S.W. Lancet (1988) [Pubmed]
  10. Novel thiols of prokaryotes. Fahey, R.C. Annu. Rev. Microbiol. (2001) [Pubmed]
  11. Adjuvant chemotherapy for adult soft tissue sarcomas of the extremities and girdles: results of the Italian randomized cooperative trial. Frustaci, S., Gherlinzoni, F., De Paoli, A., Bonetti, M., Azzarelli, A., Comandone, A., Olmi, P., Buonadonna, A., Pignatti, G., Barbieri, E., Apice, G., Zmerly, H., Serraino, D., Picci, P. J. Clin. Oncol. (2001) [Pubmed]
  12. Phase II trial of ifosfamide and mesna in advanced ovarian carcinoma: a Gynecologic Oncology Group Study. Sutton, G.P., Blessing, J.A., Homesley, H.D., Berman, M.L., Malfetano, J. J. Clin. Oncol. (1989) [Pubmed]
  13. The efficacy of mesna (2-mercaptoethane sodium sulfonate) as a uroprotectant in patients with hemorrhagic cystitis receiving further oxazaphosphorine chemotherapy. Andriole, G.L., Sandlund, J.T., Miser, J.S., Arasi, V., Linehan, M., Magrath, I.T. J. Clin. Oncol. (1987) [Pubmed]
  14. Combinations of mesna with cyclophosphamide or adriamycin in the treatment of mice with tumors. Bernacki, R.J., Bansal, S.K., Gurtoo, H.L. Cancer Res. (1987) [Pubmed]
  15. Protective effect of sodium-2-mercaptoethanesulfonate on the gastrointestinal toxicity and lethality of cis-diamminedichloroplatinum. Allan, S.G., Smyth, J.F., Hay, F.G., Leonard, R.C., Wolf, C.R. Cancer Res. (1986) [Pubmed]
  16. Pharmacokinetics and metabolism of sodium 2-mercaptoethanesulfonate in the rat. Ormstad, K., Orrenius, S., Låstbom, T., Uehara, N., Pohl, J., Stekar, J., Brock, N. Cancer Res. (1983) [Pubmed]
  17. Association of BK virus with failure of prophylaxis against hemorrhagic cystitis following bone marrow transplantation. Bedi, A., Miller, C.B., Hanson, J.L., Goodman, S., Ambinder, R.F., Charache, P., Arthur, R.R., Jones, R.J. J. Clin. Oncol. (1995) [Pubmed]
  18. Methylcobamide:coenzyme M methyltransferase isozymes from Methanosarcina barkeri. Physicochemical characterization, cloning, sequence analysis, and heterologous gene expression. LeClerc, G.M., Grahame, D.A. J. Biol. Chem. (1996) [Pubmed]
  19. Nucleotide sequence of the methyl coenzyme M reductase gene cluster from Methanosarcina barkeri. Bokranz, M., Klein, A. Nucleic Acids Res. (1987) [Pubmed]
  20. 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]
  21. Treatment of germ cell cancer with two cycles of high-dose ifosfamide, carboplatin, and etoposide with autologous stem-cell support. Margolin, B.K., Doroshow, J.H., Ahn, C., Hamasaki, V., Leong, L., Morgan, R., Raschko, J., Shibata, S., Somlo, G., Tetef, M. J. Clin. Oncol. (1996) [Pubmed]
  22. Ifosfamide/mesna. A review of its antineoplastic activity, pharmacokinetic properties and therapeutic efficacy in cancer. Dechant, K.L., Brogden, R.N., Pilkington, T., Faulds, D. Drugs (1991) [Pubmed]
  23. Phase II study of ifosfamide and mesna in patients with previously-treated carcinoma of the cervix. A Gynecologic Oncology Group study. Sutton, G.P., Blessing, J.A., Adcock, L., Webster, K.D., DeEulis, T. Investigational new drugs. (1989) [Pubmed]
  24. Intensive outpatient adjuvant therapy for breast cancer: results of dose escalation and quality of life. Swain, S.M., Rowland, J., Weinfurt, K., Berg, C., Lippman, M.E., Walton, L., Egan, E., King, D., Spertus, I., Honig, S.F. J. Clin. Oncol. (1996) [Pubmed]
  25. Received dose-intensity: a randomized trial of weekly chemotherapy with and without granulocyte colony-stimulating factor in small-cell lung cancer. Miles, D.W., Fogarty, O., Ash, C.M., Rudd, R.M., Trask, C.W., Spiro, S.G., Gregory, W.M., Ledermann, J.A., Souhami, R.L., Harper, P.G. J. Clin. Oncol. (1994) [Pubmed]
  26. Reduction of dimesna to mesna by the isolated perfused rat liver. Goren, M.P., Hsu, L.C., Li, J.T. Cancer Res. (1998) [Pubmed]
  27. Methyl coenzyme M reductase from Methanobacterium thermoautotrophicum. Resolution and properties of the components. Gunsalus, R.P., Wolfe, R.S. J. Biol. Chem. (1980) [Pubmed]
  28. Purification and properties of an enzyme involved in the ATP-dependent activation of the methanol:2-mercaptoethanesulfonic acid methyltransferase reaction in Methanosarcina barkeri. Daas, P.J., Wassenaar, R.W., Willemsen, P., Theunissen, R.J., Keltjens, J.T., van der Drift, C., Vogels, G.D. J. Biol. Chem. (1996) [Pubmed]
  29. Dependence of aldehyde dehydrogenase-mediated oxazaphosphorine resistance on soluble thiols: importance of thiol interactions with the secondary metabolite acrolein. Bunting, K.D., Townsend, A.J. Biochem. Pharmacol. (1998) [Pubmed]
  30. The CcmE protein from Escherichia coli is a haem-binding protein. Reid, E., Eaves, D.J., Cole, J.A. FEMS Microbiol. Lett. (1998) [Pubmed]
  31. In vivo generation of angiostatin isoforms by administration of a plasminogen activator and a free sulfhydryl donor: a phase I study of an angiostatic cocktail of tissue plasminogen activator and mesna. Soff, G.A., Wang, H., Cundiff, D.L., Jiang, K., Martone, B., Rademaker, A.W., Doll, J.A., Kuzel, T.M. Clin. Cancer Res. (2005) [Pubmed]
  32. Generation of the R2 subunit of ribonucleotide reductase by intein chemistry: insertion of 3-nitrotyrosine at residue 356 as a probe of the radical initiation process. Yee, C.S., Seyedsayamdost, M.R., Chang, M.C., Nocera, D.G., Stubbe, J. Biochemistry (2003) [Pubmed]
  33. Mesna and total body irradiation. Plowman, P.N., Trott, K. Lancet (1987) [Pubmed]
  34. Pharmacokinetics of an intravenous-oral versus intravenous-mesna regimen in lung cancer patients receiving ifosfamide. Goren, M.P., Anthony, L.B., Hande, K.R., Johnson, D.H., Brade, W.P., Frazier, M.W., Bush, D.A., Li, J.T. J. Clin. Oncol. (1998) [Pubmed]
  35. The magnetic and electronic properties of Methanobacterium thermoautotrophicum (strain delta H) methyl coenzyme M reductase and its nickel tetrapyrrole cofactor F430. A low temperature magnetic circular dichroism study. Hamilton, C.L., Scott, R.A., Johnson, M.K. J. Biol. Chem. (1989) [Pubmed]
  36. Crossover randomized comparison of intravenous versus intravenous/oral mesna in soft tissue sarcoma treated with high-dose ifosfamide. Mace, J.R., Keohan, M.L., Bernardy, H., Junge, K., Niebch, G., Romeis, P., Thoma, A., Wagner, T., Mueller, U., Demetri, G., Baker, L.H. Clin. Cancer Res. (2003) [Pubmed]
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