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
| Molecular Formula | C9H15N2O15P3 |
| Molecular Weight | 484.1411 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Involvement of P2Y11 receptor in silica nanoparticles 30-induced IL-6 production by human keratinocytes. | 2014-08-01 |
|
| Purinergic signaling via P2Y receptors up-mediates IL-6 production by liver macrophages/Kupffer cells. | 2014-06 |
|
| A comparative analysis of the activity of ligands acting at P2X and P2Y receptor subtypes in models of neuropathic, acute and inflammatory pain. | 2010-03 |
|
| Attenuated purinergic receptor function in patients with type 2 diabetes. | 2010-01 |
|
| Caspase-3 and -9 are activated in human myeloid HL-60 cells by calcium signal. | 2010-01 |
|
| Comparison of endothelium-related responses to nucleotides of dog and monkey cerebral arteries. | 2010 |
|
| Di-(2 ethylhexyl) phthalate and flutamide alter gene expression in the testis of immature male rats. | 2009-09-26 |
|
| 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. | 2009-06 |
|
| Uridine-5'-triphosphate protects against hepatic- ischemic/reperfusion injury in mice. | 2009-04-27 |
|
| Pharmacological characterization of pannexin-1 currents expressed in mammalian cells. | 2009-02 |
|
| Hepatitis C virus helicase/NTPase: an efficient expression system and new inhibitors. | 2008-06 |
|
| Interaction of P2 purinergic receptors with cellular macromolecules. | 2008-03 |
|
| Integrative analyses of genetic variation in enzyme activities of primary carbohydrate metabolism reveal distinct modes of regulation in Arabidopsis thaliana. | 2008 |
|
| Uridine-5'-triphosphate (UTP) maintains cardiac mitochondrial function following chemical and hypoxic stress. | 2007-11 |
|
| Comparative study of cardioprotective effects of uridine-5'-monophosphate and uridine-5'-triphosphate during the early periods of acute myocardial ischemia. | 2007-09 |
|
| Crystal structure of uridine-diphospho-N-acetylglucosamine pyrophosphorylase from Candida albicans and catalytic reaction mechanism. | 2007-06-08 |
|
| Multiple P2X receptors are involved in the modulation of apoptosis in human mesangial cells: evidence for a role of P2X4. | 2007-05 |
|
| Silencing of the Pink1 gene expression by conditional RNAi does not induce dopaminergic neuron death in mice. | 2007-03-05 |
|
| Synthesis of methylene- and difluoromethylenephosphonate analogues of uridine-4-phosphate and 3-deazauridine-4-phosphate. | 2006-12-08 |
|
| Uridine-5'-triphosphate (UTP) reduces infarct size and improves rat heart function after myocardial infarct. | 2006-10-16 |
|
| Enhancement of arachidonic acid signaling pathway by nicotinic acid receptor HM74A. | 2006-06-23 |
|
| Gene expression profiles in developing nephrons using Lim1 metanephric mesenchyme-specific conditional mutant mice. | 2006-02-07 |
|
| [Effects of Staphylococcus aureus cell-bound protein A on adenosine triphosphate and nitric oxide inhibitory actions in smooth muscles]. | 2006 |
|
| ATP- and adenosine-induced relaxation of the smooth muscle of the pig urethra. | 2005-12 |
|
| Characterization of an ecto-ATPase activity in Cryptococcus neoformans. | 2005-07 |
|
| Uridine triphosphate (UTP) is released during cardiac ischemia. | 2005-04-28 |
|
| Involvement of uracil nucleotides in protection of cardiomyocytes from hypoxic stress. | 2005-04-15 |
|
| Secretion of ATP from Schwann cells in response to uridine triphosphate. | 2005-01 |
|
| A candidate NAD+ transporter in an intracellular bacterial symbiont related to Chlamydiae. | 2004-12-02 |
|
| 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. | 2004-10-25 |
|
| Ionic interaction of amiloride and uridine 5'-triphosphate in nebulizer solutions. | 2004-09 |
|
| One-pot enzymatic synthesis of UDP-D-glucose from UMP and glucose-1-phosphate using an ATP regeneration system. | 2004-07-31 |
|
| 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. | 2004-06-22 |
|
| Expression of P2Y2 purinoceptors in MCG 101 murine sarcoma cells, and HT-29 human colon carcinoma cells. | 2004-05-31 |
|
| Cellular injury induces activation of MAPK via P2Y receptors. | 2004-04-01 |
|
| UTP transactivates epidermal growth factor receptors and promotes cardiomyocyte hypertrophy despite inhibiting transcription of the hypertrophic marker gene, atrial natriuretic peptide. | 2004-03-05 |
|
| Response to ATP is accompanied by a Ca2+ influx via P2X purinoceptors in the coronary arterioles of golden hamsters. | 2004-03 |
|
| Current treatment for primary ciliary dyskinesia conditions. | 2004-02 |
|
| Pulmonary surfactant secretion in briefly cultured mouse type II cells. | 2004-02 |
|
| Mechanically evoked reflex electrogenic chloride secretion in rat distal colon is triggered by endogenous nucleotides acting at P2Y1, P2Y2, and P2Y4 receptors. | 2004-01-26 |
|
| Mechanical stimulation releases nucleotides that activate P2Y1 receptors to trigger neural reflex chloride secretion in guinea pig distal colon. | 2004-01-26 |
|
| Uridine-5'-triphosphate and adenosine triphosphate gammaS induce mucin secretion via Ca2+-dependent pathways in human nasal epithelial cells. | 2003-12 |
|
| Pharmacotherapy of the ion transport defect in cystic fibrosis: role of purinergic receptor agonists and other potential therapeutics. | 2003 |
|
| Unblocking of chain-terminated primer by HIV-1 reverse transcriptase through a nucleotide-dependent mechanism. | 1998-11-10 |
|
| Molecular cloning and characterization of rat P2Y4 nucleotide receptor. | 1998-06 |
|
| Cloning, functional expression and tissue distribution of the human P2Y6 receptor. | 1996-05-15 |
|
| Pharmacological selectivity of the cloned human P2U-purinoceptor: potent activation by diadenosine tetraphosphate. | 1995-09 |
|
| RNA-stimulated NTPase activity associated with yellow fever virus NS3 protein expressed in bacteria. | 1993-02 |
|
| Nucleoside triphosphates promote the transformation of Ah receptor to its DNA-binding form. | 1991-03-01 |
|
| Depletion of blood plasma cytidine due to increased hepatocellular salvage in D-galactosamine-treated rats. | 1984-06-01 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:34:48 GMT 2025
by
admin
on
Mon Mar 31 17:34:48 GMT 2025
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| Record UNII |
UT0S826Z60
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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Code | English | ||
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Code | English |
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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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| Code System | Code | Type | Description | ||
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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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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
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