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M3047

Sigma-Aldrich

Mizoribine

≥98% (TLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C9H13N3O6
Número de CAS:
50924-49-7
Peso molecular:
259.22
MDL number:
MFCD00057221
UNSPSC Code:
12352200
PubChem Substance ID:
24278546
NACRES:
NA.77

Quality Level

200

assay

≥98% (TLC)

storage temp.

2-8°C

SMILES string

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

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

InChI key

HZQDCMWJEBCWBR-UUOKFMHZSA-N

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_germany

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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Kazuya Ishida et al.
Drug metabolism and pharmacokinetics, 28(1), 75-80 (2012-07-21)
Bioavailability of mizoribine in subjects with the concentrative nucleoside transporter 1 (CNT1, SLC28A1) 565-A/A allele is significantly lower than that in subjects with the SLC28A1 565-G/G allele. The aims of the present study were to investigate the cellular uptake of
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
Kohei Miyazaki et al.
Clinical nephrology, 77(4), 261-266 (2012-03-27)
Imbalance between T-helper 1 (Th1) and 2 (Th2) lymphocytes and effects of reactive oxygen species (ROS) upon glomerular capillary walls have been implicated in minimal change nephrotic syndrome (MCNS). By polymerase chain reaction and comparative genomic hybridization, we evaluated mutations
Mikiya Fujieda et al.
Clinical nephrology, 78(1), 40-46 (2012-06-27)
To evaluate the efficacy of single-dose oral mizoribine (MZB) pulse therapy given twice weekly for frequently relapsing steroid-dependent nephrotic syndrome (FR-SDNS). The subjects were 8 patients with FR-SDNS with a median age of 6.9 years old (range 3.1 - 18.0
Napoli, K.L.
J. Inter. Fed. Clin. Chem., 4, 15-15 (1992)
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