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mizoribine
Sign in to saveAlso known as bredinine, bredinin
Mizoribine (INN; MZB; trade name Bredinin) is an immunosuppressive drug. The compound was first observed in Tokyo, Japan, in 1971. It was first isolated from the fungus Penicillium brefeldianum. Mizoribine 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
Chemical data
- Formula
- C9H13N3O6
- Molecular weight
- 259.22 g/mol
- IUPAC name
- 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide
- SMILES
- C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)N
- InChIKey
- HZQDCMWJEBCWBR-UUOKFMHZSA-N
- XLogP
- -1.9
- Polar surface area
- 151 Ų
- H-bond donors
- 5
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- rheumatoid arthritis, nephrotic syndrome, lupus nephritis
via ChEMBL · EBI
Research
809 papers- Mizoribine or Cyclophosphamide for Lupus Nephritis: A Randomized Clinical Trial.JAMA network open · 2025
- [Mizoribine].Nihon rinsho. Japanese journal of clinical medicine · 2005
- Mizoribine Promotes Molecular Chaperone HSP60/HSP10 Complex Formation.International journal of molecular sciences · 2024
- Mizoribine in the treatment of pediatric-onset glomerular disease.World journal of pediatrics : WJP · 2015
- Mizoribine and mycophenolate mofetil.Current medicinal chemistry · 1999
via PubMed
Wikidata facts
- Mass
- 259.08
- Has use
- medication
Show 4 more facts
- subject has role
- antimalarial
- chemical formula
- C₉H₁₃N₃O₆
- isomeric SMILES
- C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)N
- canonical SMILES
- C1=NC(=C(N1C2C(C(C(O2)CO)O)O)O)C(=O)N
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Mizoribine (INN; MZB; trade name Bredinin) is an immunosuppressive drug. The compound was first observed in Tokyo, Japan, in 1971. It was first isolated from the fungus Penicillium brefeldianum. Mizoribine 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 ==
Excerpted from Wikipedia’s “mizoribine” article, available under the CC BY-SA 4.0 licence.