Nitrofurantoin monohydrateProduct ingredient for Nitrofurantoin
- Name
- Nitrofurantoin monohydrate
- 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
- DBSALT001891
- Structure
Structure for Nitrofurantoin monohydrate (DBSALT001891)
- Synonyms
- Furadantin monohydrate / Nitrofurantoin, monohydrate / Nitrofurantoinum monohydrate
- UNII
- E1QI2CQQ1I
- CAS Number
- 17140-81-7
- Weight
- Average: 256.174
Monoisotopic: 256.044383994 - Chemical Formula
- C8H8N4O6
- InChI Key
- NHBPVLAHAVEISO-JSGFVSQVSA-N
- InChI
- InChI=1S/C8H6N4O5.H2O/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);1H2/b9-3+;
- IUPAC Name
- 4-hydroxy-1-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-2,5-dihydro-1H-imidazol-2-one hydrate
- SMILES
- O.[H]\C(=N/N1CC(O)=NC1=O)C1=CC=C(O1)N(=O)=O
- External Links
- ChemSpider
- 7845474
- Predicted Properties
Property Value Source Water Solubility 0.194 mg/mL ALOGPS logP -0.25 ALOGPS logP 0.15 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 4.46 Chemaxon pKa (Strongest Basic) -2.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 124.22 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 53.44 m3·mol-1 Chemaxon Polarizability 20.57 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon