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Mizoribine

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This is the current revision of this page, as edited by Citation bot (talk | contribs) at 15:26, 9 December 2024 (Added doi. | Use this bot. Report bugs. | Suggested by Dominic3203 | Linked from User:Marbletan/sandbox | #UCB_webform_linked 75/2664). The present address (URL) is a permanent link to this version.

Revision as of 15:26, 9 December 2024 by Citation bot (talk | contribs) (Added doi. | Use this bot. Report bugs. | Suggested by Dominic3203 | Linked from User:Marbletan/sandbox | #UCB_webform_linked 75/2664)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Immunosuppressive drug Pharmaceutical compound
Mizoribine
Clinical data
Other names1--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
IUPAC name
  • 5-hydroxy-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.164.876 Edit this at Wikidata
Chemical and physical data
FormulaC9H13N3O6
Molar mass259.218 g·mol
3D model (JSmol)
SMILES
  • C1=NC(=C(N12(((O2)CO)O)O)O)C(=O)N
InChI
  • 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. 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. doi:10.2174/092986730607220401123549. PMID 10390602.
Immunosuppressive drugs / Immunosuppressants (L04)
Intracellular
(initiation)
Antimetabolites
Macrolides/
other IL-2 inhibitors
IMiDs
Intracellular
(reception)
IL-1 receptor antagonists
mTOR
Extracellular
Antibodies
Monoclonal
Serum target
(noncellular)
Cellular
target
Unsorted
Polyclonal
-cept (Fusion)
Unsorted
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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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