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M3047

Sigma-Aldrich

Mizoribine

≥98% (TLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C9H13N3O6
Numéro CAS:
50924-49-7
Poids moléculaire :
259.22
Numéro MDL:
MFCD00057221
Code UNSPSC :
12352200
ID de substance PubChem :
24278546
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥98% (TLC)

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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)

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H315,H319,H335,H360

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

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S Hirohata et al.
Journal of immunology (Baltimore, Md. : 1950), 155(11), 5175-5183 (1995-12-01)
Mizoribine has been used to prevent rejection of organ allografts in humans and in animal models. Recent clinical trials have demonstrated its efficacy in rheumatoid arthritis and lupus nephritis, in which abnormalities of B cell functions are also involved. We
C V Catapano et al.
Molecular pharmacology, 47(5), 948-955 (1995-05-01)
Inhibitors of IMP dehydrogenase (EC 1.2.1.14), including mizoribine (Bredinin) and mycophenolic acid, have significant antitumor and immunosuppressive activities. Studies were aimed at determining the mechanism by which intracellular GTP depletion induced by these agents results in inhibition of DNA synthesis.
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
Hideo Ohtsubo et al.
Modern rheumatology, 22(6), 837-843 (2012-03-07)
The efficacy of mizoribine (MZR) in treatment of rheumatoid arthritis (RA) was retrospectively investigated in terms of drug survival, improvement in Disease Activity Score-28 (DAS28)-C-reactive protein (CRP), and blood MZR concentration obtained 3 h after dosing (MZR-C3). To compare the efficacy
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