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

• ChemBase编号: 72651
• 分子式: C9H13N3O6
• 平均质量: 259.21602
• 单一同位素质量: 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

名称和登记号

名称

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

登记号

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

理论计算性质

• Acid pKa: 8.186375
• 质子受体: 7
• 质子供体: 5
• LogD (pH = 5.5): -2.0362294
• LogD (pH = 7.4): -2.0982585
• Log P: -2.032959
• 摩尔折射率: 55.5497 cm^3
• 极化性: 21.993095 Å^3
• 极化表面积: 151.06 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

安全信息

• 保存条件: -20°C
• RTECS编号: NI3980000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 46-60-61-36/37/38
• 安全公开号: 53-22-26-36/37/39-45
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H319-H335-H360
• GHS警示性声明: P201-P261-P305 + P351 + P338-P308 + P313
• 个人保护装置: 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
• 保存温度: 2-8°C

药理学性质

• 作用靶点: DNA/RNA synthesis

产品相关信息

• 纯度: ≥98% (TLC)
• 成盐信息: Free Base

详细说明

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.

参考文献

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