Nitrofurantoin

Base Information

• Chemical Name: Nitrofurantoin
• CAS No.: 67-20-9
• Molecular Formula: C8H6N4O5
• Molecular Weight: 238.159
• Hs Code.: 29349990
• European Community (EC) Number: 200-646-5
• NSC Number: 757243
• UNII: 927AH8112L
• Wikipedia: Nitrofurantoin
• NCI Thesaurus Code: C29293
• RXCUI: 7454
• Pharos Ligand ID: 6Q2MRUBQXX7J
• ChEMBL ID: CHEMBL572
• Mol file: 67-20-9.mol

Synonyms:Furadantin;Furadantine;Furadoine;Furadonine;Furantoin;Macrodantin;Nitrofurantoin;Nitrofurantoin Sodium Salt;Nitrofurantoin, Monohydrate

Chemical Property of Nitrofurantoin

Chemical Property:

• Appearance/Colour: lemon yellow crystalline powder
• Melting Point: 268 °C
• Refractive Index: 1.744
• Boiling Point: 380.75°C (rough estimate)
• PKA: 7.2(at 25℃)
• PSA: 120.73000
• Density: 1.81 g/cm³
• LogP: 0.86340
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive & Hygroscopic
• Solubility.: DMF: soluble50mg/mL
• Water Solubility.: <0.01 g/100 mL at 19℃
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 238.03381930
• Heavy Atom Count: 17
• Complexity: 390

Purity/Quality:

98.0%~102.0% ^*data from raw suppliers

Nitrofurantoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiinfective Agents, Urinary (Nitrofuran Derivative)
• Canonical SMILES: C1C(=O)NC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
• Isomeric SMILES: C1C(=O)NC(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-]
• Recent ClinicalTrials: Comparative Study to Evaluate Efficacy and Safety of Gepotidacin to Nitrofurantoin in Treatment of Uncomplicated Urinary Tract Infection (UTI)
• Recent EU Clinical Trials: Clinical effectiveness and bacteriological eradication of 3 short-course antibiotic regimens and single-dose of fosfomicyn trometamol for lower urinary tract infections in adult women [SCOUT study].
• Uses: counterirritant A nitrofuran antibiotic with low resistance potential that is rapidly metabolized by mammals. Active against both Gram-positive and Gram-negative bacteria. Nitrofurantoin is also a prooxidant that is cytotoxic due to the generation of intracellular H2O2. Antibacterial. A nitrofuran antibiotic with low resistance potential that is rapidly metabolized by mammals. Active against both Gram-positive and Gram-negative bacteria. Nitrofurantoin is also a prooxidant that is cytotoxic due to the generation of intracellular H2O2. Antibacterial.Environmental contaminants; Food contaminants; Heat processing contaminants
• Indications: Like nitrofurazone, nitrofurantoin is an effective drug that acts on a number of Grampositive and Gram-negative microorganisms (staphylococci, streptococci, dysentery bacillus, colon bacillus, paratyphoid bacillus, and others). It is primarily used for treating infectious diseases of the urinary tract (pyelitis, pyelonephritis, cystitis, urethritis). Synonyms of this drug are furadonin, ituran, phenurin, urolong, cistofuran, nitrofurin, and many others.
• Clinical Use: Acute dysuria and frequency Bacteriuria in pregnancy Prophylaxis of recurrent cystitis (reduced dosage)
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Nitrofurantoin

There total 9 articles about Nitrofurantoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1-aminohydantoin (6301-02-6) + 5-nitrofurane-2-carboxaldehyde (698-63-5) → Nitrofurantoin (67-20-9)

Guidance literature:

1-aminohydantoin; With acetic acid; In water; for 0.0833333h; Sonication;

5-nitrofurane-2-carboxaldehyde; In dimethyl sulfoxide; at 20 ℃; for 0.5h; Sonication;

DOI:10.1016/j.taap.2020.115104

Reference yield: 95.0%

5-nitrofurane-2-carboxaldehyde (698-63-5) + 1-aminohydantoin hydrochloride (2827-56-7) → Nitrofurantoin (67-20-9)

Guidance literature:

With zirconium(IV) oxide; for 0.25h;

DOI:10.1039/c8gc01345d

Reference yield: 70.0%

5-nitro-2-furfuraldehyde diacetate (92-55-7) + 1-aminohydantoin hydrochloride (2827-56-7) → Dantafur (67-20-9)

Guidance literature:

1-aminohydantoin hydrochloride; With sulfuric acid; acetic acid; In water; at 20 ℃; Large scale;

5-nitro-2-furfuraldehyde diacetate; In ethanol; water; at 90 ℃; for 3h; Large scale;

upstream raw materials:

1-aminohydantoin

5-nitro-2-furfuraldehyde diacetate

3-(5-nitrofurfurylideneamino)hydantoic acid

5-nitrofurane-2-carboxaldehyde

Downstream raw materials:

1-aminohydantoin

1-aminohydantoin hydrochloride

Refernces

• 1、 Gallardo-Garrido,Cho,Cortés-Rios,Vasquez,Pessoa-Mahana,Araya-Maturana,Pessoa-Mahana,Faundez. "Nitrofuran drugs beyond redox cycling: Evidence of Nitroreduction-independent cytotoxicity mechanism". . . Retrieved 2020/06/23.
• 2、 -. "Process for formulating a synthetic drug for use in animal feed, and resulting formulation". . . Retrieved 2008/06/13.