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Chemical Compound Review

Levoleucovorin     (2S)-2-[[4-[[(6S)-2-amino-5- methanoyl-4...

Synonyms: Levofolene, levo-Folinic, L-Folinic acid, AG-G-64159, CHEBI:63606, ...
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Disease relevance of folinic acid


High impact information on folinic acid

  • We also determined the plasma pharmacokinetics of folates after intravenous (IV) injection of (6S)-folinic acid at the dose used in this study [6].
  • They may have implications for the identification of patients resistant to FU chemotherapy and for a better understanding and management of FU modulation by folinic acid (FA) [7].
  • We investigated the biological activities of the natural and unnatural diastereoisomers of 5-formyltetrahydrofolate [(6S)- and (6R)-5-HCO-H4PteGlu, respectively, both 99.99% pure], using a human ileocecal carcinoma cell line (HCT-8) [8].
  • [6RS]Leucovorin (5-formyltetrahydrofolate; 5-CHO-H4PteGlu) administered in different regimens in combination with 5-fluorouracil (FUra) has increased the response rates to FUra in patients with colon adenocarcinoma [9].
  • We used our model of HD-MTX neurotoxicity in the rat to determine if leucovorin (5-formyltetrahydrofolate) reduces this neurotoxicity, and extended our characterization of this model to identify regional as well as global HD-MTX treatment effects and to investigate HD-MTX-induced alterations in regional brain pH [10].

Chemical compound and disease context of folinic acid


Biological context of folinic acid


Anatomical context of folinic acid


Associations of folinic acid with other chemical compounds


Gene context of folinic acid


Analytical, diagnostic and therapeutic context of folinic acid

  • HD-MTX (8 g/m2) therapy with 5-formyltetrahydrofolate "rescue" (stage III) was usually begun about seven weeks after start of chemotherapy, and the patients were followed for two to eight courses separated by three to eight weeks [34].
  • CONCLUSIONS: Relative to high-dose FA, high-dose oral L-folinic acid-based supplementation does not afford improved tHcy-lowering efficacy in hemodialysis patients [12].
  • We present a rapid, sensitive, and automated HPLC method with direct resolution of l-folinic acid (l-FA), d-folinic acid (d-FA), and 5-methyltetrahydrofolate (5MTHF) from plasma samples [35].
  • The thermodynamic parameters for the binding of 5-formyltetrahydrofolate (5-CHO-H4PteGlun) and its polyglutamate forms to rabbit liver cytosolic serine hydroxymethyltransferase (SHMT) were determined by a combination of isothermal titration calorimetry and spectrophotometry [36].
  • Adjuvant chemotherapy (5-FU + l-folinic acid) was delivered to 26 patients in the FUMIR-T4 protocol group [37].


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  6. Fluorouracil combined with the pure (6S)-stereoisomer of folinic acid in high doses for treatment of patients with advanced colorectal carcinoma: a phase I-II study. Machover, D., Grison, X., Goldschmidt, E., Zittoun, J., Lotz, J.P., Metzger, G., Richaud, J., Hannoun, L., Marquet, J., Guillot, T. J. Natl. Cancer Inst. (1992) [Pubmed]
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  10. High-dose leucovorin reverses acute high-dose methotrexate neurotoxicity in the rat. Phillips, P.C., Thaler, H.T., Allen, J.C., Rottenberg, D.A. Ann. Neurol. (1989) [Pubmed]
  11. Loss of reduced folate carrier function and folate depletion result in enhanced pemetrexed inhibition of purine synthesis. Zhao, R., Zhang, S., Hanscom, M., Chattopadhyay, S., Goldman, I.D. Clin. Cancer Res. (2005) [Pubmed]
  12. Rapid communication: L-folinic acid versus folic acid for the treatment of hyperhomocysteinemia in hemodialysis patients. Yango, A., Shemin, D., Hsu, N., Jacques, P.F., Dworkin, L., Selhub, J., Bostom, A.G. Kidney Int. (2001) [Pubmed]
  13. Colorectal cancer in the adjuvant setting: perspectives on treatment and the role of prognostic factors. Cascinu, S., Georgoulias, V., Kerr, D., Maughan, T., Labianca, R., Ychou, M. Ann. Oncol. (2003) [Pubmed]
  14. Current treatments and future perspectives in colorectal and gastric cancer. Wilke, H.J., Van Cutsem, E. Ann. Oncol. (2003) [Pubmed]
  15. Modulation of 5-fluorouracil as adjuvant systemic chemotherapy in colorectal cancer: the IGCS-COL multicentre, randomised, phase III study. De Placido, S., Lopez, M., Carlomagno, C., Paoletti, G., Palazzo, S., Manzione, L., Iannace, C., Ianniello, G.P., De Vita, F., Ficorella, C., Farris, A., Pistillucci, G., Gemini, M., Cortesi, E., Adamo, V., Gebbia, N., Palmeri, S., Gallo, C., Perrone, F., Persico, G., Bianco, A.R. Br. J. Cancer (2005) [Pubmed]
  16. Mechanism for the coupling of ATP hydrolysis to the conversion of 5-formyltetrahydrofolate to 5,10-methenyltetrahydrofolate. Huang, T., Schirch, V. J. Biol. Chem. (1995) [Pubmed]
  17. The 6S- and 6R-diastereomers of 5, 10-dideaza-5, 6, 7, 8-tetrahydrofolate are equiactive inhibitors of de novo purine synthesis. Moran, R.G., Baldwin, S.W., Taylor, E.C., Shih, C. J. Biol. Chem. (1989) [Pubmed]
  18. 5-Formyltetrahydrofolate polyglutamates are slow tight binding inhibitors of serine hydroxymethyltransferase. Stover, P., Schirch, V. J. Biol. Chem. (1991) [Pubmed]
  19. Methotrexate transport in variant human CCRF-CEM leukemia cells with elevated levels of the reduced folate carrier. Selective effect on carrier-mediated transport of physiological concentrations of reduced folates. Jansen, G., Westerhof, G.R., Jarmuszewski, M.J., Kathmann, I., Rijksen, G., Schornagel, J.H. J. Biol. Chem. (1990) [Pubmed]
  20. Oxidation of 10-formyltetrahydrofolate to 10-formyldihydrofolate by complex IV of rat mitochondria. Brookes, P.S., Baggott, J.E. Biochemistry (2002) [Pubmed]
  21. Hydrolysis of 5,10-methenyltetrahydrofolate to 5-formyltetrahydrofolate at pH 2.5 to 4.5. Baggott, J.E. Biochemistry (2000) [Pubmed]
  22. Uptake of 5-formyltetrahydrofolate in isolated rat liver mitochondria is carrier-mediated. Horne, D.W., Holloway, R.S., Said, H.M. J. Nutr. (1992) [Pubmed]
  23. Pharmacological mobilization of haemopoietic progenitor cells in human peripheral blood. Berardi, A., Geraci, L., Quaglietta, A.M., Di Bartolomeo, G., Dragani, A. Haematologica (1990) [Pubmed]
  24. Transport of 5-formyltetrahydrofolate into primary cultured rat astrocytes. Cai, S., Horne, D.W. Arch. Biochem. Biophys. (2003) [Pubmed]
  25. Methotrexate rescue by 5-methyltetrahydrofolate or 5-formyltetrahydrofolate in lymphoblast cell lines. Dudman, N.P., Slowiaczek, P., Tattersall, M.H. Cancer Res. (1982) [Pubmed]
  26. Methenyltetrahydrofolate synthetase regulates folate turnover and accumulation. Anguera, M.C., Suh, J.R., Ghandour, H., Nasrallah, I.M., Selhub, J., Stover, P.J. J. Biol. Chem. (2003) [Pubmed]
  27. Identification of protein-arginine N-methyltransferase as 10-formyltetrahydrofolate dehydrogenase. Kim, S., Park, G.H., Joo, W.A., Paik, W.K., Cook, R.J., Williams, K.R. J. Biol. Chem. (1998) [Pubmed]
  28. Vector targeting makes 5-fluorouracil chemotherapy less toxic and more effective in animal models of epithelial neoplasms. Akbulut, H., Tang, Y., Maynard, J., Zhang, L., Pizzorno, G., Deisseroth, A. Clin. Cancer Res. (2004) [Pubmed]
  29. A prominent low-pH methotrexate transport activity in human solid tumors: contribution to the preservation of methotrexate pharmacologic activity in HeLa cells lacking the reduced folate carrier. Zhao, R., Gao, F., Hanscom, M., Goldman, I.D. Clin. Cancer Res. (2004) [Pubmed]
  30. Characterization of two cDNAs encoding folate-binding proteins from L1210 murine leukemia cells. Increased expression associated with a genomic rearrangement. Brigle, K.E., Westin, E.H., Houghton, M.T., Goldman, I.D. J. Biol. Chem. (1991) [Pubmed]
  31. Cloning and characterization of the human 5,10-methenyltetrahydrofolate synthetase-encoding cDNA. Dayan, A., Bertrand, R., Beauchemin, M., Chahla, D., Mamo, A., Filion, M., Skup, D., Massie, B., Jolivet, J. Gene (1995) [Pubmed]
  32. Thymidylate synthase and methylenetetrahydrofolate reductase gene polymorphisms: relationships with 5-fluorouracil sensitivity. Etienne, M.C., Ilc, K., Formento, J.L., Laurent-Puig, P., Formento, P., Cheradame, S., Fischel, J.L., Milano, G. Br. J. Cancer (2004) [Pubmed]
  33. Cloning and characterization of mitochondrial 5-formyltetrahydrofolate cycloligase from higher plants. Roje, S., Janave, M.T., Ziemak, M.J., Hanson, A.D. J. Biol. Chem. (2002) [Pubmed]
  34. Plasma homocysteine in children with acute lymphoblastic leukemia: changes during a chemotherapeutic regimen including methotrexate. Refsum, H., Wesenberg, F., Ueland, P.M. Cancer Res. (1991) [Pubmed]
  35. HPLC of folinic acid diastereoisomers and 5-methyltetrahydrofolate in plasma. Etienne, M.C., Speziale, N., Milano, G. Clin. Chem. (1993) [Pubmed]
  36. Thermodynamic analysis of the binding of the polyglutamate chain of 5-formyltetrahydropteroylpolyglutamates to serine hydroxymethyltransferase. Huang, T., Wang, C., Maras, B., Barra, D., Schirch, V. Biochemistry (1998) [Pubmed]
  37. Does downstaging predict improved outcome after preoperative chemoradiation for extraperitoneal locally advanced rectal cancer? A long-term analysis of 165 patients. Valentini, V., Coco, C., Picciocchi, A., Morganti, A.G., Trodella, L., Ciabattoni, A., Cellini, F., Barbaro, B., Cogliandolo, S., Nuzzo, G., Doglietto, G.B., Ambesi-Impiombato, F., Cosimelli, M. Int. J. Radiat. Oncol. Biol. Phys. (2002) [Pubmed]
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