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Nifurtoinol

Nifurtoinol structure

CAS No:
1088-92-2
Formula:
C9H8N4O6
Chemical Name:
Nifurtoinol
Synonyms:
2,4-Imidazolidinedione,3-(hydroxymethyl)-1-[[(5-nitro-2-furanyl)methylene]amino]-;Hydantoin,3-(hydroxymethyl)-1-[(5-nitrofurfurylidene)amino]-;3-(Hydroxymethyl)-1-[[(5-nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione;3-(Hydroxymethyl)-1-(5-nitrofurfurylideneamino)hydantoin;Urfadyn;Hydroxymethylnitrofurantoin;1-(5-Nitro-2-furfurylidenamino)-3-hydroxymethylhydantoin;Urfadine;Nifurtoinol
Categories:
Organic Chemistry > Nitro Compounds

Description

ChEBI: An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group and at position 3 by a hydroxymethyl group.

Nifurtoinol is an imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group and at position 3 by a hydroxymethyl group. It has a role as an antiinfective agent, an antibacterial drug and a hepatotoxic agent. It is a nitrofuran antibiotic, an imidazolidine-2,4-dione, an organonitrogen heterocyclic antibiotic and a hydrazone. It derives from a semicarbazide.|Nifurtoinol is a derivative of nitrofuran used as an antibiotic in the treatment of urinary tract infections. Nifurtoinol is bactericidal to most gram-positive and gram-negative urinary tract pathogens.

Nifurtoinol Basic Attributes

Molecular Weight：

268.185

Exact Mass：

268.18

EC Number：

214-126-0

UNII：

980688H13O

DSSTox ID：

DTXSID30148747

NCI Thesaurus Code：

C90997

ATC Code：

J01XE02|J - Antiinfectives for systemic use

Characteristics

PSA：

132

XLogP3：

0.13470

Density：

1.5401 (rough estimate)

Melting Point：

258 °C (decomp)

Boiling Point：

411.35°C (rough estimate)

Flash Point：

224.6ºC

Refractive Index：

1.6590 (estimate)

Vapor Pressure：

0mmHg at 25°C

Drug Information

MeSH：

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

MeSH Entry Terms：

3-hydroxymethylnitrofurantoin

Nifurtoinol Use and Manufacturing

The hydroxymethyl derivative of nitrofurantoin, formulated for oral administration. The activity is similar to that of nitrofurantoin. Little is known about the pharmacokinetic behavior. It is said to be more rapidly absorbed than nitrofurantoin and excreted into the urine to a greater extent. Available in some countries in continental Europe.

Computed Properties

Molecular Weight:268.18
XLogP3:-0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:268.04438399
Monoisotopic Mass:268.04438399
Topological Polar Surface Area:132
Heavy Atom Count:19
Complexity:433
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes