Denufosol

HCID 9875516

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Grundinformationen

CAS: 211448-85-0
Standard-SMILES: Nc1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4ccc(=O)[nH]c4=O)[C@H](O)[C@@H]3O)O2)c(=O)n1
InChIKey: FPNPSEMJLALQSA-MIYUEGBISA-N
Summenformel: C18H27N5O21P4
Durchschnittliche Molmasse: 773,3 g/mol
Monoisotopische Masse: 773,01490088

Überblick

Denufosol was an inhaled drug used for the treatment of cystic fibrosis (CF), showing various improvements in lung function during a phase III clinical trial. A new drug application (NDA) was filed with the FDA in 2011, however, the second phase III clinical trial showed a lack of improvement in lung function for cystic fibrosis patients taking denufosol. The drug was also evaluated in the treatment of retinal detachment and other diseases of the retina. Denufosol has not gained FDA approval, and clinical trials with this drug have ceased since 2011.

Namen und Bezeichner

Bevorzugter Name: Denufosol
IUPAC: [[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate

Namen und Synonyme

denufosol211448-85-0Denufosol [INN]dCp4UUp4dC5PC250KSSHDENUFOSOL [MI]UNII-5PC250KSSHDENUFOSOL [WHO-DD]INS3721INS 3721[[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate

Weitere Namen anzeigen

P(1)-(Uridine 5')-P(4)-(2'-deoxycytidine 5')tetraphosphate, tetrasodium salt[[[[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphatedenufosolum(((((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl) ((2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl hydrogen phosphate(((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((((2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl) hydrogen phosphateRefChem:131884CHEMBL507282Uridine 5'-(pentahydrogen tetraphosphate), 2'-deoxy-, P''' inverted exclamation marku5'-ester with cytidine

Datenbank-Bezeichner

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -8,4
Polarare Oberfläche (TPSA): 383 Å²
H-Brücken-Donoren: 9
H-Brücken-Akzeptoren: 21
Frei drehbare Bindungen: 14
Schwere Atome: 48
Formalladung: 0
Komplexität: 1.590

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

Denufosol is designed to enhance the lung's innate mucosal hydration and mucociliary clearance through stimulation of the P2Y2 receptor. The pharmacologic profile of denufosol parallels that of UTP, leading to increased chloride and water secretion, increased cilia beat frequency, and increased mucin release.

Mechanism of Action · 1 Eintrag

Denufosol tetrasodium is a selective P2Y2 agonist designed to enhance the lung's innate mucosal hydration and mucociliary clearance mechanisms by activating an alternative ion channel that acts in the same way as the defective ion channel in moving salt and water to the surface of the airways. Based on pre-clinical and clinical work, denufosol has several pharmacological actions contributing to its mechanism of action: hydration of the airways by stimulating chloride and liquid secretions on the epithelial cell surface; inhibition of epithelial sodium absorption; enhancement of ciliary beat frequency; and stimulation of mucin secretion. This unique mechanism of action represents a differentiated approach relative to other approved CF products and may be important in intervening in the early clinical course of CF lung disease.

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