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Nitrofurantoin

Nitrofurantoin Structure
CAS No.
67-20-9
Chemical Name:
Nitrofurantoin
Synonyms
Furadantin;Macrodantin;macrobid;NITROFURANTOINE;Furalan;Dantafur;Furantoin;Upiol;Furina;Cystit
CBNumber:
CB7346080
Molecular Formula:
C8H6N4O5
Molecular Weight:
238.16
MOL File:
67-20-9.mol
MSDS File:
SDS
Modify Date:
2024/7/26 15:15:06

Nitrofurantoin Properties

Melting point 268°C
Boiling point 380.75°C (rough estimate)
Density 1.5824 (rough estimate)
refractive index 1.6700 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility DMF: soluble50mg/mL
pka 7.2(at 25℃)
form crystalline
color yellow
Water Solubility <0.01 g/100 mL at 19 ºC
Sensitive Light Sensitive & Hygroscopic
λmax 358nm(MeOH)(lit.)
Merck 14,6599
BRN 893207
BCS Class 2
Stability Stability Stable, but light-sensitive. Combustible. Incompatible with strong oxidizing agents, strong alkalies, strong acids. Decomposes upon contact with most metals other than stainless steel and aluminium.
CAS DataBase Reference 67-20-9(CAS DataBase Reference)
NIST Chemistry Reference Hydantoin, n-(5-nitro-2-furfurylidene)-1-amino-(67-20-9)
IARC 3 (Vol. 50) 1990
EPA Substance Registry System Nitrofurantoin (67-20-9)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H317-H334
Precautionary statements  P261-P264-P280-P301+P312-P302+P352-P304+P340+P312
Hazard Codes  Xn
Risk Statements  22-42/43
Safety Statements  22-36/37-45
RIDADR  2811
WGK Germany  3
RTECS  MU2800000
TSCA  Yes
HazardClass  6.1(b)
PackingGroup  III
HS Code  29349990
Toxicity LD50 oral in rat: 604mg/kg
NFPA 704
1
2 0

Nitrofurantoin price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) N7878 Nitrofurantoin 98.0-102.0% (EP, UV) 67-20-9 10G ₹3420.7 2022-06-14 Buy
Sigma-Aldrich(India) N7878 Nitrofurantoin 98.0-102.0% (EP, UV) 67-20-9 25G ₹5250.13 2022-06-14 Buy
Sigma-Aldrich(India) PHR1191 Nitrofurantoin Pharmaceutical Secondary Standard; Certified Reference Material 67-20-9 1G ₹8508.45 2022-06-14 Buy
Sigma-Aldrich(India) N7878 Nitrofurantoin 98.0-102.0% (EP, UV) 67-20-9 100G ₹12362.15 2022-06-14 Buy
Sigma-Aldrich(India) N7878 Nitrofurantoin 98.0-102.0% (EP, UV) 67-20-9 250G ₹15425.63 2022-06-14 Buy
Product number Packaging Price Buy
N7878 10G ₹3420.7 Buy
N7878 25G ₹5250.13 Buy
PHR1191 1G ₹8508.45 Buy
N7878 100G ₹12362.15 Buy
N7878 250G ₹15425.63 Buy

Nitrofurantoin Chemical Properties,Uses,Production

Chemical Properties

lemon yellow crystalline powder

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.

Definition

ChEBI: An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.

Antimicrobial activity

It is active against almost all the common urinary pathogens, except Proteus mirabilis. It is bactericidal.
It antagonizes the activity of nalidixic acid and other quinolones in vitro, but this combination is unlikely to be used clinically.

Acquired resistance

Surprisingly for an agent that has been used for so long, resistance remains uncommon. R-factor-mediated resistance has been reported, but this appears to be very unusual. The mechanism of resistance seems to be a decreased nitroreductase activity in the target organism.
There is cross-resistance within the nitrofuran group, but none with antibiotics of other chemical classes.

General Description

Odorless lemon yellow crystals or fine yellow powder. Bitter taste.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Nitrofurantoin is sensitive to light. Nitrofurantoin is incompatible with alkalis. Nitrofurantoin is also incompatible with strong oxidizers and strong acids. Nitrofurantoin decomposes on contact with metals other than stainless steel and aluminum.

Hazard

Questionable carcinogen.

Fire Hazard

Flash point data for Nitrofurantoin are not available; however, Nitrofurantoin is probably combustible.

Pharmaceutical Applications

A synthetic compound available only for oral administration. There are three formulations, differing in their crystalline nature: microcrystalline, macrocrystalline, and a delayedrelease preparation containing a combination of the two. The macrocrystalline form is said to be less liable to give rise to the most common adverse event, nausea. However, pharmacokinetic and clinical trial evidence for this assertion is not very strong.
It is slightly soluble in water (c. 200 mg/L) but more so in dilute alkali. Solubility in ethanol is modest (500 mg/L), but the compound dissolves very well in dimethylformamide (80 g/L). If packaged in light-resistant containers and kept at room temperature, it is stable for more than 5 years. The yellow solution should be kept in the dark.

Clinical Use

Acute dysuria and frequency
Bacteriuria in pregnancy
Prophylaxis of recurrent cystitis (reduced dosage)

Safety Profile

Poison by ingestion and intraperitoneal routes. Human systemic effects: peripheral motor nerve recording changes, ataxia, changes in urine composition, and hemolysis with or without anemia. Human reproductive effects by ingestion: spermatogenesis. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Nitrofurantoin Preparation Products And Raw materials

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