Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H12N2O15P3.3Na.2H2O |
| Molecular Weight | 586.1171 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[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=KIYVKLDQLQZXKH-GTIFRNKBSA-K
InChI=1S/C9H15N2O15P3.3Na.2H2O/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);;;;2*1H2/q;3*+1;;/p-3/t4-,6-,7-,8-;;;;;/m1...../s1
| Molecular Formula | C9H14N2O15P3 |
| Molecular Weight | 483.1331 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | HO |
| Molecular Weight | 17.0073 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| Pharmacological selectivity of the cloned human P2U-purinoceptor: potent activation by diadenosine tetraphosphate. | 1995 Sep |
|
| 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 |
|
| Characterization and mutational analysis of the helicase and NTPase activities of hepatitis C virus full-length NS3 protein. | 1999 Mar |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| One-pot enzymatic synthesis of UDP-D-glucose from UMP and glucose-1-phosphate using an ATP regeneration system. | 2004 Jul 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 Jun 22 |
|
| Involvement of uracil nucleotides in protection of cardiomyocytes from hypoxic stress. | 2005 Apr 15 |
|
| 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 |
|
| Uridine-5'-triphosphate (UTP) maintains cardiac mitochondrial function following chemical and hypoxic stress. | 2007 Nov |
|
| Integrative analyses of genetic variation in enzyme activities of primary carbohydrate metabolism reveal distinct modes of regulation in Arabidopsis thaliana. | 2008 |
|
| Hepatitis C virus helicase/NTPase: an efficient expression system and new inhibitors. | 2008 Jun |
|
| 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 |
|
| Attenuated purinergic receptor function in patients with type 2 diabetes. | 2010 Jan |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:49:46 GMT 2023
by
admin
on
Sat Dec 16 09:49:46 GMT 2023
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| Record UNII |
05161190OB
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| Record Status |
Validated (UNII)
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| Record Version |
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SUB121912
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116295-90-0
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05161190OB
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admin on Sat Dec 16 09:49:46 GMT 2023 , Edited by admin on Sat Dec 16 09:49:46 GMT 2023
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |