Nitrofurantoin sodiumProduct ingredient for Nitrofurantoin

Name
Nitrofurantoin sodium
Drug Entry
Nitrofurantoin

Nitrofurantoin is a nitrofuran antibiotic used to treat uncomplicated urinary tract infections.8,9,10 Nitrofurantoin is converted by bacterial nitroreductases to electrophilic intermediates which inhibit the citric acid cycle as well as synthesis of DNA, RNA, and protein.2 This drug is more resistant to the development of bacterial resistance because it acts on many targets at once.2 Nitrofurantoin is a second line treatment to trimethoprim/sulfamethoxazole.3

Nitrofurantoin was granted FDA approval on 6 February 1953.11

Accession Number
DBSALT001418
Structure
Synonyms
Not Available
UNII
MAL9M0T5LV
CAS Number
54-87-5
Weight
Average: 260.141
Monoisotopic: 260.01576356
Chemical Formula
C8H5N4NaO5
InChI Key
AFDJQFFKYDCYIG-JSGFVSQVSA-M
InChI
InChI=1S/C8H6N4O5.Na/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16;/h1-3H,4H2,(H,10,13,14);/q;+1/p-1/b9-3+;
IUPAC Name
sodium 3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-2,5-dioxoimidazolidin-1-ide
SMILES
[Na+].[O-][N+](=O)C1=CC=C(O1)\C=N\N1CC(=O)[N-]C1=O
ChemSpider
7838271
ChEMBL
CHEMBL1201000
Wikipedia
Nitrofurantoin
Predicted Properties
PropertyValueSource
Water Solubility0.809 mg/mLALOGPS
logP-0.29ALOGPS
logP-0.22Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.23Chemaxon
pKa (Strongest Basic)-2.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area115.25 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity51.31 m3·mol-1Chemaxon
Polarizability20.06 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon