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M3047

Sigma-Aldrich

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
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

Signal Word

Danger

Hazard Statements

H315,H319,H335,H360

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Napoli, K.L.
J. Inter. Fed. Clin. Chem., 4, 15-15 (1992)
Long-term multidrug therapy in an adolescent patient with proliferative lupus nephritis: a trial of less cytotoxic therapy.
Tomomi Aizawa-Yashiro et al.
Clinical nephrology, 78(4), 332-334 (2012-08-03)
Topical Application of Mizoribine Suppresses CD4+ T-cell-Mediated Pathogenesis in Murine Dry Eye
Zhang X, et al.
Investigative Ophthalmology & Visual Science, 58(14), 6056-6064 (2017)
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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