Denufosol tetrasodiumProduct ingredient for Denufosol

Name
Denufosol tetrasodium
Drug Entry
Denufosol

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.

Accession Number
DBSALT000847
Structure
Synonyms
P1-(Uridine 5'-)-P4-(2'-Deoxycytidine 5'-) Tetraphosphate, Tetrasodium Salt
External IDs
INS37217
UNII
82M942WZ4A
CAS Number
318250-11-2
Weight
Average: 861.25
Monoisotopic: 860.94267789
Chemical Formula
C18H23N5Na4O21P4
InChI Key
PASYJVRFGUDDEW-WMUGRWSXSA-J
InChI
InChI=1S/C18H27N5O21P4.4Na/c19-11-1-3-22(17(28)20-11)13-5-8(24)9(40-13)6-38-45(30,31)42-47(34,35)44-48(36,37)43-46(32,33)39-7-10-14(26)15(27)16(41-10)23-4-2-12(25)21-18(23)29;;;;/h1-4,8-10,13-16,24,26-27H,5-7H2,(H,30,31)(H,32,33)(H,34,35)(H,36,37)(H2,19,20,28)(H,21,25,29);;;;/q;4*+1/p-4/t8-,9+,10+,13+,14+,15+,16+;;;;/m0..../s1
IUPAC Name
tetrasodium [(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [({[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}phosphinato)oxy]phosphonate
SMILES
[Na+].[Na+].[Na+].[Na+].NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP([O-])(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)O1
PubChem Compound
10219163
ChemSpider
8394655
ChEMBL
CHEMBL1767407
Wikipedia
Denufosol
Predicted Properties
PropertyValueSource
Water Solubility38.8 mg/mLALOGPS
logP0.86ALOGPS
logP-5.4Chemaxon
logS-1.4ALOGPS
pKa (Strongest Acidic)0.76Chemaxon
pKa (Strongest Basic)0.13Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count18Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area393.92 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity140.83 m3·mol-1Chemaxon
Polarizability58.23 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon