Mizoribine

Immunosuppressive drug

none

Legal statusLegal status

In general: ℞ (Prescription only)

Identifiers

IUPAC name

5-hydroxy-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide

CAS Number

50924-49-7^Y

PubChem CID

104762

ChemSpider

94571

UNII

4JR41A10VP

KEGG

D01392^Y

CompTox Dashboard (EPA)

DTXSID8045777

ECHA InfoCard100.164.876

Chemical and physical dataFormulaC₉H₁₃N₃O₆Molar mass259.218 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](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.^[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

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

Immunosuppressive drugs / Immunosuppressants (L04)

Intracellular
(initiation)

Antimetabolites	purine synthesis inhibitors Azathioprine Mycophenolic acid dihydroorotate dehydrogenase inhibitors Leflunomide Teriflunomide antifolate Methotrexate
Macrolides/ other IL-2 inhibitors	FKBP/Cyclophilin/Calcineurin Ciclosporin Pimecrolimus Tacrolimus Voclosporin Abetimus Gusperimus
IMiDs	Lenalidomide Pomalidomide Thalidomide PDE4 inhibitor Apremilast

Intracellular
(reception)

IL-1 receptor antagonists	Anakinra
mTOR	Everolimus Ridaforolimus Sirolimus Temsirolimus Umirolimus Zotarolimus

Extracellular

Antibodies

Monoclonal

Serum target (noncellular)	Complement component 5 Eculizumab TNF Adalimumab Afelimomab Certolizumab pegol Golimumab Infliximab Nerelimomab Interleukin Anakinra Basiliximab Bimekizumab Briakinumab Brodalumab Canakinumab Daclizumab Guselkumab Ixekizumab Netakimab Olokizumab Rilonacept Risankizumab Sarilumab Satralizumab Secukinumab Siltuximab Sirukumab Spesolimab Tildrakizumab Tocilizumab Ustekinumab Interleukin 5 Mepolizumab Immunoglobulin E Omalizumab Interferon Faralimomab IL-6 Elsilimomab IL-12 and IL-23 Lebrikizumab Ustekinumab IL-17A Secukinumab
Cellular target	CD3 Muromonab-CD3 Otelixizumab Teplizumab Visilizumab CD4 Clenoliximab Keliximab Zanolimumab CD11a Efalizumab CD18 Erlizumab CD20 Obinutuzumab Ocrelizumab Pascolizumab Rituximab Ublituximab CD23 Gomiliximab Lumiliximab CD40 Teneliximab Toralizumab CD62L/L-selectin Aselizumab CD80 Galiximab CD147/Basigin Gavilimomab CD154 Frexalimab Ruplizumab BLyS Belimumab CAT Bertilimumab Lerdelimumab Metelimumab Integrin Natalizumab Vedolizumab Interleukin-6 receptor Tocilizumab LFA-1 Odulimomab IL-2 receptor/CD25 Basiliximab Daclizumab Inolimomab T-lymphocyte (Zolimomab aritox)
Unsorted	Alemtuzumab Anifrolumab Atorolimumab Begelomab Cedelizumab Emapalumab Fontolizumab Inebilizumab Maslimomab Morolimumab Ofatumumab Pexelizumab Reslizumab Rovelizumab Siplizumab Talizumab Telimomab aritox Teprotumumab Vapaliximab Vepalimomab

Polyclonal

-cept (Fusion)

CTLA-4
- Abatacept
- Belatacept
TNF inhibitor
- Etanercept
- Opinercept
Aflibercept
Alefacept
Rilonacept

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.