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Product Details:

  • Product Name: Leucovorin
  • CAS #: 1492-18-8
  • Mode of Action:

    As leucovorin is a derivative of folic acid, it can be used to increase levels of folic acid under conditions favoring folic acid inhibition (following treatment of folic acid antagonists such as methotrexate). Leucovorin enhances the activity of fluorouracil by stabilizing the bond of the active metabolite (5-FdUMP) to the enzyme thymidylate synthetase.

  • Pharmacodynamics:

    Leucovorin is one of several active, chemically reduced derivatives of folic acid. It is useful as an antidote to drugs which act as folic acid antagonists. Leucovorin is a mixture of the diastereoisomers of the 5-formyl derivative of tetrahydrofolic acid (THF). The biologically active compound of the mixture is the (-)-l-isomer, known as Citrovorum factor or (-)-folinic acid. Leucovorin does not require reduction by the enzyme dihydrofolate reductase in order to participate in reactions utilizing folates as a source of “one-carbon” moieties. Administration of leucovorin can counteract the therapeutic and toxic effects of folic acid antagonists such as methotrexate, which act by inhibiting dihydrofolate reductase. Leucovorin has also been used to enhance the activity of fluorouracil.

  • Metabolism:

    Hepatic and intestinal mucosal, the main metabolite being the active 5-methyltetrahydrofolate. Leucovorin is readily converted to another reduced folate, 5, 10-methylenetetrahydrofolate, which acts to stabilize the binding of fluorodeoxyridylic acid to thymidylate synthase and thereby enhances the inhibition of this enzyme.

  • Toxicity:

    LD50>8000 mg/kg (orally in rats). Excessive amounts of leucovorin may nullify the chemotherapeutic effect of folic acid antagonists.

  • IUPAC: (2R)-2-[(4-{[(2-amino-5-formyl-4-oxo-1, 4, 5, 6, 7, 8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
  • DrugBank: DB00650
  • Formula: C20H23N7O7
  • Molecular Mass: 473.4393
  • Synonyms: 10-Formyl-7,8-dihydrofolic acid, 5-Formyl-5,6,7,8-tetrahydrofolic acid, 5-Formyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid, 5-Formyltetrahydrofolic acid, Acide folinique, CF, EINECS 200-361-6, Folinate, Folinic acid, Folinic acid-SF, HSDB 6544, l-Leucovorin, Leucal, Leucoverin, Leucovorin, Leucovorinum (acid), N5-Formyl-5,6,7,8-tetrahydrofolic acid, N5-Formyltetrahydrofolic acid, UNII-Q573I9DVLP, Welcovorin
  • SMILES: c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCC2CNc3c(c(=O)nc([nH]3)N)N2C=O
  • AHFS Code: 32:00.0
  • InChl: 1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12?,13-/m0/s1
  • General Reference:


    1. Jardine LF, Ingram LC, Bleyer WA: Intrathecal leucovorin after intrathecal methotrexate overdose. J Pediatr Hematol Oncol. 1996 Aug;18(3):302-4. Pubmed


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