SML3058

Diquafosol tetrasodium

>95% (HPLC)

• Synonym(s): Diuridine 5′-tetraphosphate, sodium salt, INS365, KPY 998, P ,P -Diuridine 5′-tetraphosphate tetrasodium salt, Up4U 4Na, Uridine 5′-(pentahydrogen tetraphosphate), P′′′→5′-ester with uridine, sodium salt (1:4), Diuridine 5′-tetraphosphate, Up4U tetrasodium
• Empirical Formula (Hill Notation): C₁₈H₂₂N₄Na₄O₂₃P₄
• CAS Number: 211427-08-6
• Molecular Weight: 878.23
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: >95% (HPLC)
• form: powder
• optical activity: [α]/D -12.0 to -8.0°, c = 1.0 in H₂O
• color: white to beige
• solubility: H₂O: 2 mg/mL, clear
• storage temp.: −20°C
• SMILES string: [Na].[Na].[Na].[Na].[P](=O)(O[P](=O)(O[P](=O)(OC[C@H]3O[C@H]([C@@H]([C@@H]3O)O)N4C=CC(=O)NC4=O)O)O)(O[P](=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N2C=CC(=O)NC2=O)O)O
• InChI: 1S/C18H26N4O23P4.4Na/c23-9-1-3-21(17(29)19-9)15-13(27)11(25)7(41-15)5-39-46(31,32)43-48(35,36)45-49(37,38)44-47(33,34)40-6-8-12(26)14(28)16(42-8)22-4-2-10(24)20-18(22)30;;;;/h1-4,7-8,11-16,25-28H,5-6H2,(H,31,32)(H,33,34)(H,35,36)(H,37,38)(H,19,23,29)(H,20
• InChI key: MHPMESDJCUICEY-FNXFGIETSA-N

Description

Biochem/physiol Actions

Diquafosol (Up4U, INS365) is a selective purinergic receptor P2Y2 agonist (EC50 = 100 nM/P2Y2, 400 nM/P2Y4, 20 μM/P2Y6, >100 μM/P2Y1 by calcium mobilization using respective 1321N P2Y subtype transfectants). In addition to its in vivo efficacy in anmial dry eye models, diquafosol is also shown to enhance mucociliary clearance in sheep and stimulate vaginal moisture in ovariectomized rabbits.

P2Y₂/P2Y₄ purinoceptor agonist: EC₅₀ = 0.10 μM at P2Y₂, 0.4 μM at P2Y₄ (20 μM at P2Y₆) in 1321N astrocytoma cells infected with a retrovirus encoding the human P2Y_1, P2Y_2, P2Y₄ and P2Y₆

Diagnostic Implications

In clinical development for the treatment of dry eye and chronic lung disease, such as cystic fibrosis

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable