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Merck
CN

M3047

Mizoribine

≥98% (TLC)

Synonym(s):

N′-(β-D-Ribofuranosyl)-5-hydroxy­imida­zole-4-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C9H13N3O6
CAS Number:
50924-49-7
Molecular Weight:
259.22
NACRES:
NA.77
PubChem Substance ID:
24278546
UNSPSC Code:
12352200
MDL number:
MFCD00057221

Key Documents

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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

SMILES string

NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1O

InChI key

HZQDCMWJEBCWBR-UUOKFMHZSA-N

assay

≥98% (TLC)

storage temp.

2-8°C

Quality Level

200

Application

Mizoribine has been used in topical treatment to evaluate its effect on ocular surface damage of dry eye in B6 mice subjected to desiccating stress (DS). It has also been used as an inosine monophosphate dehydrogenase (IMPDH) inhibitor to test its in vivo efficacy.

Biochem/physiol Actions

Mizoribine is an imidazole nucleoside possessing strong immunosuppressive properties. It selectively blocks T-cell proliferation response to mitogenic and allo-antigenic stimulation. Mizoribine blocks the movement of T cells from G to S phase. In addition, it significantly decreases the number of B cells at the S, G, and M phases. Mizoribine inhibits de novo synthesis of nucleotides by inhibition of inosine monophosphate dehydrogenase. The resulting nucleotide depletion inhibits DNA synthesis.(3)

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000480160
0000480160
0000471973
0000471973
128M4079V

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Inosine monophosphate dehydrogenase dependence in a subset of small cell lung cancers
Huang F, et al.
Cell Metabolism, 28(3), 369-382 (2018)
A Nomura et al.
Lupus, 21(13), 1444-1449 (2012-08-25)
The prognosis of lupus nephritis (LN) has improved since the introduction of immunosuppressant therapies, but the safety and effectiveness of treatments can also be improved. We retrospectively assessed the treatment courses of 12 patients with systemic lupus erythematosus who were
Larry A Greenbaum et al.
Nature reviews. Nephrology, 8(8), 445-458 (2012-06-13)
The introduction of corticosteroids more than 50 years ago dramatically improved the prognosis of children with nephrotic syndrome. Corticosteroids remain the standard initial treatment for children with this disease, but a considerable proportion of patients do not respond and are
Shigeaki Nakazawa et al.
Hinyokika kiyo. Acta urologica Japonica, 59(2), 103-106 (2013-04-05)
We report a case of hyperuricemia and acute kidney injury associated with mizoribine (MZR). A 15- year-old male with congenital renal hypoplasia underwent kidney transplantation. We used tacrolimus extended release (0.15 mg/kg/day), mizoribine (MZR) (12 mg/kg/day), prednisolone and basiliximab as
Michitoshi Yamashita et al.
Cell transplantation, 21(2-3), 535-545 (2012-07-17)
Mizoribine (MZ) inhibits the differentiation and proliferation of helper T and B cells after antigen recognition by suppressing the purine biosynthesis pathway and nucleic acid synthesis. MZ has been used in kidney transplantation, but distinct data are unavailable for islet
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