Mizoribine

Mizoribine
Clinical data
Other names	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide
AHFS/Drugs.com	International 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	50924-49-7 ;
PubChem CID	104762;
ChemSpider	94571;
UNII	4JR41A10VP;
KEGG	D01392 ;
CompTox Dashboard (EPA)	DTXSID8045777 ;
ECHA InfoCard	100.164.876
Chemical and physical data
Formula	C9H13N3O6
Molar mass	259.218 g·mol−1
3D 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.

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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.

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

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