Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H15N2O15P3 |
| Molecular Weight | 484.1411 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
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=PGAVKCOVUIYSFO-XVFCMESISA-N
InChI=1S/C9H15N2O15P3/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)/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 |
|---|---|---|
| Depletion of blood plasma cytidine due to increased hepatocellular salvage in D-galactosamine-treated rats. | 1984 Jun 1 |
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| Nucleoside triphosphates promote the transformation of Ah receptor to its DNA-binding form. | 1991 Mar 1 |
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| Pharmacological selectivity of the cloned human P2U-purinoceptor: potent activation by diadenosine tetraphosphate. | 1995 Sep |
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| Molecular cloning and characterization of rat P2Y4 nucleotide receptor. | 1998 Jun |
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| Unblocking of chain-terminated primer by HIV-1 reverse transcriptase through a nucleotide-dependent mechanism. | 1998 Nov 10 |
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| The serine protease and RNA-stimulated nucleoside triphosphatase and RNA helicase functional domains of dengue virus type 2 NS3 converge within a region of 20 amino acids. | 1999 Apr |
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| Characterization and mutational analysis of the helicase and NTPase activities of hepatitis C virus full-length NS3 protein. | 1999 Mar |
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| Measuring apoptosis in human spermatozoa: a biological assay for semen quality? | 2000 Aug |
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| Pyridoxal-phosphate-6-azophenyl-2',4'-disulfonate (PPADS), a putative P2Y(1) receptor antagonist, blocks signaling at a site distal to the receptor in Madin-Darby canine kidney-D(1) cells. | 2000 Jan |
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| ATP, an agonist at the rat P2Y(4) receptor, is an antagonist at the human P2Y(4) receptor. | 2000 May |
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| 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 |
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| In vitro investigations of tumor targeting with (99m)Tc-labeled antisense DNA. | 2001 Nov |
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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 |
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| Expression of c-Myc and other apoptosis-related genes in Swiss Webster mouse fetuses after maternal exposure to all trans-retinoic acid. | 2002 May-Jun |
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| Pharmacotherapy of the ion transport defect in cystic fibrosis: role of purinergic receptor agonists and other potential therapeutics. | 2003 |
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| 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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| An endothelium-derived factor modulates purinergic neurotransmission to mesenteric arterial smooth muscle of hamster. | 2003 Feb 14 |
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| Characterization of a Ca2+ response to both UTP and ATP at human P2Y11 receptors: evidence for agonist-specific signaling. | 2003 Jun |
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| Expression and function of P2X purinoceptors in rat histaminergic neurons. | 2003 Mar |
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| Cellular injury induces activation of MAPK via P2Y receptors. | 2004 Apr 1 |
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| A candidate NAD+ transporter in an intracellular bacterial symbiont related to Chlamydiae. | 2004 Dec 2 |
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| Current treatment for primary ciliary dyskinesia conditions. | 2004 Feb |
|
| Mechanical stimulation releases nucleotides that activate P2Y1 receptors to trigger neural reflex chloride secretion in guinea pig distal colon. | 2004 Jan 26 |
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| Cumulus expansion, nuclear maturation and connexin 43, cyclooxygenase-2 and FSH receptor mRNA expression in equine cumulus-oocyte complexes cultured in vitro in the presence of FSH and precursors for hyaluronic acid synthesis. | 2004 Jun 22 |
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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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| Expression of P2Y2 purinoceptors in MCG 101 murine sarcoma cells, and HT-29 human colon carcinoma cells. | 2004 May 31 |
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| Ionic interaction of amiloride and uridine 5'-triphosphate in nebulizer solutions. | 2004 Sep |
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| [Effects of Staphylococcus aureus cell-bound protein A on adenosine triphosphate and nitric oxide inhibitory actions in smooth muscles]. | 2006 |
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| Gene expression profiles in developing nephrons using Lim1 metanephric mesenchyme-specific conditional mutant mice. | 2006 Feb 7 |
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| Enhancement of arachidonic acid signaling pathway by nicotinic acid receptor HM74A. | 2006 Jun 23 |
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| Comparative study of cardioprotective effects of uridine-5'-monophosphate and uridine-5'-triphosphate during the early periods of acute myocardial ischemia. | 2007 Sep |
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| Integrative analyses of genetic variation in enzyme activities of primary carbohydrate metabolism reveal distinct modes of regulation in Arabidopsis thaliana. | 2008 |
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| Uridine-5'-triphosphate protects against hepatic- ischemic/reperfusion injury in mice. | 2009 Apr 27 |
|
| Pharmacological characterization of pannexin-1 currents expressed in mammalian cells. | 2009 Feb |
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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FDA ORPHAN DRUG |
99096
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NCI_THESAURUS |
C1937
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FDA ORPHAN DRUG |
93495
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DTXSID0041147
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m11335
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15713
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100000077319
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3639
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46398
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6133
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200-558-7
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63-39-8
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DB04005
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UT0S826Z60
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URIDINE TRIPHOSPHATE
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C2613
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SUB15669MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
