Mizoribine

Mizoribine (INN; MZB; trade name Bredinin) is an immunosuppressive drug. The compound was first observed in Tokyo, Japan, in 1971.^[1] 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.

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
administrationOral

ATC code

• none

Quick facts Clinical data, Other names ...

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 Y
PubChem CID	104762
ChemSpider	94571
UNII	4JR41A10VP
KEGG	D01392 Y
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
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