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
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
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Nucleoside triphosphates promote the transformation of Ah receptor to its DNA-binding form. | 1991 Mar 1 |
|
| Pharmacological selectivity of the cloned human P2U-purinoceptor: potent activation by diadenosine tetraphosphate. | 1995 Sep |
|
| Unblocking of chain-terminated primer by HIV-1 reverse transcriptase through a nucleotide-dependent mechanism. | 1998 Nov 10 |
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| Characterization and mutational analysis of the helicase and NTPase activities of hepatitis C virus full-length NS3 protein. | 1999 Mar |
|
| Safety of aerosolized INS 365 in patients with mild to moderate cystic fibrosis: results of a phase I multi-center study. | 2001 Aug |
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| Release of ATP by a human retinal pigment epithelial cell line: potential for autocrine stimulation through subretinal space. | 2001 Jul 1 |
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| Differential effects of UTP, ATP, and adenosine on ciliary activity of human nasal epithelial cells. | 2001 Jun |
|
| Protective effect of heme oxygenase-1 gene transfer against oxyhemoglobin-induced endothelial dysfunction. | 2001 Oct |
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| Identification of the P2Y(12) receptor: a novel member of the P2Y family of receptors activated by extracellular nucleotides. | 2001 Sep |
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| [The effect of uridine and uridine nucleotides on isolated rat heart performance in regional myocardial ischemia]. | 2002 Apr-Jun |
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| Methanocarba modification of uracil and adenine nucleotides: high potency of Northern ring conformation at P2Y1, P2Y2, P2Y4, and P2Y11 but not P2Y6 receptors. | 2002 Jan 3 |
|
| Uridine-5'-triphosphate and adenosine triphosphate gammaS induce mucin secretion via Ca2+-dependent pathways in human nasal epithelial cells. | 2003 Dec |
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| Current treatment for primary ciliary dyskinesia conditions. | 2004 Feb |
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| Response to ATP is accompanied by a Ca2+ influx via P2X purinoceptors in the coronary arterioles of golden hamsters. | 2004 Mar |
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| UTP transactivates epidermal growth factor receptors and promotes cardiomyocyte hypertrophy despite inhibiting transcription of the hypertrophic marker gene, atrial natriuretic peptide. | 2004 Mar 5 |
|
| The RNA helicase, nucleotide 5'-triphosphatase, and RNA 5'-triphosphatase activities of Dengue virus protein NS3 are Mg2+-dependent and require a functional Walker B motif in the helicase catalytic core. | 2004 Oct 25 |
|
| Ionic interaction of amiloride and uridine 5'-triphosphate in nebulizer solutions. | 2004 Sep |
|
| Characterization of an ecto-ATPase activity in Cryptococcus neoformans. | 2005 Jul |
|
| [Effects of Staphylococcus aureus cell-bound protein A on adenosine triphosphate and nitric oxide inhibitory actions in smooth muscles]. | 2006 |
|
| Gene expression profiles in developing nephrons using Lim1 metanephric mesenchyme-specific conditional mutant mice. | 2006 Feb 7 |
|
| Enhancement of arachidonic acid signaling pathway by nicotinic acid receptor HM74A. | 2006 Jun 23 |
|
| Uridine-5'-triphosphate (UTP) reduces infarct size and improves rat heart function after myocardial infarct. | 2006 Oct 16 |
|
| Crystal structure of uridine-diphospho-N-acetylglucosamine pyrophosphorylase from Candida albicans and catalytic reaction mechanism. | 2007 Jun 8 |
|
| Uridine-5'-triphosphate (UTP) maintains cardiac mitochondrial function following chemical and hypoxic stress. | 2007 Nov |
|
| Comparative study of cardioprotective effects of uridine-5'-monophosphate and uridine-5'-triphosphate during the early periods of acute myocardial ischemia. | 2007 Sep |
|
| Interaction of P2 purinergic receptors with cellular macromolecules. | 2008 Mar |
|
| Uridine-5'-triphosphate protects against hepatic- ischemic/reperfusion injury in mice. | 2009 Apr 27 |
|
| Interleukin-1beta enhances nucleotide-induced and alpha-secretase-dependent amyloid precursor protein processing in rat primary cortical neurons via up-regulation of the P2Y(2) receptor. | 2009 Jun |
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| Di-(2 ethylhexyl) phthalate and flutamide alter gene expression in the testis of immature male rats. | 2009 Sep 26 |
|
| Attenuated purinergic receptor function in patients with type 2 diabetes. | 2010 Jan |
|
| Caspase-3 and -9 are activated in human myeloid HL-60 cells by calcium signal. | 2010 Jan |
|
| A comparative analysis of the activity of ligands acting at P2X and P2Y receptor subtypes in models of neuropathic, acute and inflammatory pain. | 2010 Mar |
|
| Involvement of P2Y11 receptor in silica nanoparticles 30-induced IL-6 production by human keratinocytes. | 2014 Aug 1 |
Patents
Sample Use Guides
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
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SUB70959
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243-347-5
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88265
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20260
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100000135528
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19817-92-6
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GM3E161I3C
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ACTIVE MOIETY
SUBSTANCE RECORD
