1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxy-1H-imidazole-4-carboxamide

• ChemBase ID: 72651
• Molecular Formular: C9H13N3O6
• Molecular Mass: 259.21602
• Monoisotopic Mass: 259.08043515
• SMILES: [C@H]1(O[C@@H]([C@H]([C@H]1O)O)CO)n1c(c(nc1)C(=O)N)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc(c1O)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
• InChIKey: HZQDCMWJEBCWBR-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxy-1H-imidazole-4-carboxamide
• IUPAC Traditional name: bredinin
• Synonyms: N′-(β-D-Ribofuranosyl)-5-hydroxy-imida-zole-4-carboxamide; Mizoribine; Bredinin; Mizoribine

Database IDs

• CAS Number: 50924-49-7
• MDL Number: MFCD00057221
• PubChem SID: 24278546; 162037576
• PubChem CID: 104762

CALCULATED PROPERTIES

• Acid pKa: 8.186375
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.0362294
• LogD (pH = 7.4): -2.0982585
• Log P: -2.032959
• Molar Refractivity: 55.5497 cm^3
• Polarizability: 21.993095 Å^3
• Polar Surface Area: 151.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: NI3980000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 46-60-61-36/37/38
• Safety Statements: 53-22-26-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H360
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: DNA/RNA synthesis

Product Information

• Purity: ≥98% (TLC)
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1384

Research Area: Immunology
Biological Activity:
Mizoribine (Bredinin) is an imidazole nucleoside and an immunosuppressive agent with an IC50 of approximately 100 μM. The immunosuppressive effect of mizoribine (Bredinin) has been reported to be due to the inhibition of DNA synthesis in the S phase of the cell cycle. Because of its relative lack of toxicity, during the past decade mizoribine (Bredinin) has been frequently used instead of azathioprine as a component of immunosuppressive drug regimens. Mizoribine (Bredinin) is being used to treat renal transplantation patients, IgA nephropathy, lupus erythematosus, and childhood nephrotic syndrome (NS), and some recent studies have assessed the efficacy of oral mizoribine (Bredinin) pulse therapy for severe lupus nephritis, steroid-resistant NS, and frequently relapsing-steroid-dependent NS. [1][2][3]

Sigma Aldrich - M3047

Biochem/physiol Actions
Mizoribine is an imidazole nucleoside possessing strong immunosuppressive properties. 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.

REFERENCES

• http://en.wikipedia.org/wiki/Mizoribine