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 |
|---|---|---|
| Depletion of blood plasma cytidine due to increased hepatocellular salvage in D-galactosamine-treated rats. | 1984 Jun 1 |
|
| Nucleoside triphosphates promote the transformation of Ah receptor to its DNA-binding form. | 1991 Mar 1 |
|
| RNA-stimulated NTPase activity associated with yellow fever virus NS3 protein expressed in bacteria. | 1993 Feb |
|
| Pharmacological selectivity of the cloned human P2U-purinoceptor: potent activation by diadenosine tetraphosphate. | 1995 Sep |
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| Cloning, functional expression and tissue distribution of the human P2Y6 receptor. | 1996 May 15 |
|
| Molecular cloning and characterization of rat P2Y4 nucleotide receptor. | 1998 Jun |
|
| Unblocking of chain-terminated primer by HIV-1 reverse transcriptase through a nucleotide-dependent mechanism. | 1998 Nov 10 |
|
| 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 |
|
| Characterization and mutational analysis of the helicase and NTPase activities of hepatitis C virus full-length NS3 protein. | 1999 Mar |
|
| Measuring apoptosis in human spermatozoa: a biological assay for semen quality? | 2000 Aug |
|
| 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 |
|
| ATP, an agonist at the rat P2Y(4) receptor, is an antagonist at the human P2Y(4) receptor. | 2000 May |
|
| Safety of aerosolized INS 365 in patients with mild to moderate cystic fibrosis: results of a phase I multi-center study. | 2001 Aug |
|
| Release of ATP by a human retinal pigment epithelial cell line: potential for autocrine stimulation through subretinal space. | 2001 Jul 1 |
|
| Differential effects of UTP, ATP, and adenosine on ciliary activity of human nasal epithelial cells. | 2001 Jun |
|
| In vitro investigations of tumor targeting with (99m)Tc-labeled antisense DNA. | 2001 Nov |
|
| Protective effect of heme oxygenase-1 gene transfer against oxyhemoglobin-induced endothelial dysfunction. | 2001 Oct |
|
| Identification of the P2Y(12) receptor: a novel member of the P2Y family of receptors activated by extracellular nucleotides. | 2001 Sep |
|
| [The effect of uridine and uridine nucleotides on isolated rat heart performance in regional myocardial ischemia]. | 2002 Apr-Jun |
|
| 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 |
|
| ATP can enhance the proton-induced CGRP release through P2Y receptors and secondary PGE(2) release in isolated rat dura mater. | 2002 Jun |
|
| 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 |
|
| An endothelium-derived factor modulates purinergic neurotransmission to mesenteric arterial smooth muscle of hamster. | 2003 Feb 14 |
|
| Characterization of a Ca2+ response to both UTP and ATP at human P2Y11 receptors: evidence for agonist-specific signaling. | 2003 Jun |
|
| Expression and function of P2X purinoceptors in rat histaminergic neurons. | 2003 Mar |
|
| A candidate NAD+ transporter in an intracellular bacterial symbiont related to Chlamydiae. | 2004 Dec 2 |
|
| Current treatment for primary ciliary dyskinesia conditions. | 2004 Feb |
|
| Pulmonary surfactant secretion in briefly cultured mouse type II cells. | 2004 Feb |
|
| Mechanically evoked reflex electrogenic chloride secretion in rat distal colon is triggered by endogenous nucleotides acting at P2Y1, P2Y2, and P2Y4 receptors. | 2004 Jan 26 |
|
| Mechanical stimulation releases nucleotides that activate P2Y1 receptors to trigger neural reflex chloride secretion in guinea pig distal colon. | 2004 Jan 26 |
|
| One-pot enzymatic synthesis of UDP-D-glucose from UMP and glucose-1-phosphate using an ATP regeneration system. | 2004 Jul 31 |
|
| UTP transactivates epidermal growth factor receptors and promotes cardiomyocyte hypertrophy despite inhibiting transcription of the hypertrophic marker gene, atrial natriuretic peptide. | 2004 Mar 5 |
|
| Ionic interaction of amiloride and uridine 5'-triphosphate in nebulizer solutions. | 2004 Sep |
|
| Involvement of uracil nucleotides in protection of cardiomyocytes from hypoxic stress. | 2005 Apr 15 |
|
| Uridine triphosphate (UTP) is released during cardiac ischemia. | 2005 Apr 28 |
|
| Characterization of an ecto-ATPase activity in Cryptococcus neoformans. | 2005 Jul |
|
| Synthesis of methylene- and difluoromethylenephosphonate analogues of uridine-4-phosphate and 3-deazauridine-4-phosphate. | 2006 Dec 8 |
|
| 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 |
|
| Silencing of the Pink1 gene expression by conditional RNAi does not induce dopaminergic neuron death in mice. | 2007 Mar 5 |
|
| 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 |
|
| Hepatitis C virus helicase/NTPase: an efficient expression system and new inhibitors. | 2008 Jun |
|
| Interaction of P2 purinergic receptors with cellular macromolecules. | 2008 Mar |
|
| 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 |
|
| 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 |
|
| Purinergic signaling via P2Y receptors up-mediates IL-6 production by liver macrophages/Kupffer cells. | 2014 Jun |
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
Fri Dec 15 15:00:17 GMT 2023
by
admin
on
Fri Dec 15 15:00:17 GMT 2023
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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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-
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Systematic Name | English | ||
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Common Name | English | ||
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Code | English | ||
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Code | English |
| Classification Tree | Code System | Code | ||
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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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