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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H12N2O15P3.3Na
Molecular Weight 550.0866
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URIDINE 5'-TRIPHOSPHATE SODIUM

SMILES

[Na+].[Na+].[Na+].O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP([O-])(=O)OP([O-])(=O)OP(O)([O-])=O)N2C=CC(=O)NC2=O

InChI

InChIKey=MMJGIWFJVDOPJF-LLWADOMFSA-K
InChI=1S/C9H15N2O15P3.3Na/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18;;;/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18);;;/q;3*+1/p-3/t4-,6-,7-,8-;;;/m1.../s1

HIDE SMILES / InChI

Description

Uridine 5'-triphosphate (UTP, INS316) is a naturally occurring agonist for P2Y(2) receptors on the apical surface of ciliated respiratory epithelium. INS316, being developed by Inspire Pharmaceuticals, is a short-acting, aerosolized uridine 5-triphosphate (UTP) solution used as a diagnostic aid for lung cancer. INS316 appears to improve sputum expectoration mediated through the P2Y2 receptor, a nucleotide receptor expressed in human airway epithelial cells and some other tissues. UTP binding to the P2Y2 receptor triggers signal transduction that leads to chloride ion secretion, thereby resulting in mucociliary clearance of airway. UTP stimulates salt and water transport and cilia beat frequency in human airway epithelium in vitro. Single, inhaled doses of UTP stimulate mucociliary clearance in conscious, intubated sheep and in patients with mild chronic bronchitis (smokers and former smokers), suggesting that UTP may be useful for obtaining deep-lung sputum specimens suitable for diagnostic purposes. A single dose of INS316 safely improves the ability of patients with mild chronic bronchitis to expectorate a deep-lung sputum specimen suitable for cytologic evaluation.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Mild chronic bronchitis: patients attempted to expectorate a specimen spontaneously, following a single inhaled dose of Uridine 5'-triphosphate (10 to 180 mg).
Route of Administration: Respiratory
In Vitro Use Guide
Uridine 5'-triphosphate is a stimulator (EC50 = 2.1 uM) of increase in intracellular calcium concentrations in cells cultured from guinea-pig cardiac endothelium (CEC).