Mizoribine

Mizoribine
Clinical data
Other names1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 5-hydroxy-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide
CAS Number
  • 50924-49-7 checkY
PubChem CID
  • 104762
ChemSpider
  • 94571
UNII
  • 4JR41A10VP
KEGG
  • D01392 checkY
CompTox Dashboard (EPA)
  • DTXSID8045777
ECHA InfoCard100.164.876
Chemical and physical data
FormulaC9H13N3O6
Molar mass259.218 g·mol−1
3D model (JSmol)
  • Interactive image
  • C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)N
  • InChI=1S/C9H13N3O6/c10-7(16)4-8(17)12(2-11-4)9-6(15)5(14)3(1-13)18-9/h2-3,5-6,9,13-15,17H,1H2,(H2,10,16)/t3-,5-,6-,9-/m1/s1
  • Key:HZQDCMWJEBCWBR-UUOKFMHZSA-N
  (verify)

Mizoribine (INN, trade name Bredinin) is an immunosuppressive drug. The compound was first observed in Tokyo, Japan, in 1971.[1] First isolated from the fungus Penicillium brefeldianum. Mizoribine (MZB) is an imidazole nucleoside that has been used in renal transplantation, and in steroid-resistant nephrotic syndrome, IgA nephropathy, lupus, as well as for adults with rheumatoid arthritis, lupus nephritis and other rheumatic diseases. MZB exerts its activity through selective inhibition of inosine monophosphate dehydrogenase and guanosine monophosphate synthetase, resulting in the complete inhibition of guanine nucleotide synthesis without incorporation into nucleotides. It arrests DNA synthesis in the S phase of cellular division. Thus, MZB has less toxicity than azathioprine, another immunosuppressant used for some of the same diseases.

References

  1. ^ Ishikawa H (July 1999). "Mizoribine and mycophenolate mofetil". Current Medicinal Chemistry. 6 (7). Bentham Science: 575–97. PMID 10390602.

Mizoribine (MZB) is an imidazole nucleoside that has been used in renal transplantation, and in steroid-resistant nephrotic syndrome, IgA nephropathy, lupus, as well as for adults with rheumatoid arthritis, lupus nephritis and other rheumatic diseases. MZB exerts its activity through selective inhibition of inosine monophosphate synthetase and guanosine monophosphate synthetase, resulting in the complete inhibition of guanine nucleotide synthesis without incorporation into nucleotides. It arrests DNA synthesis in the S phase of cellular division. Thus, MZB has less toxicity than azathioprine, another immunosuppressant used for some of the same diseases.

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