Nifurtoinol

Chemical compound

J01XE02 (WHO)

Pharmacokinetic dataExcretionRenal (40–50% within the first 12 hours)Identifiers

IUPAC name

3-(hydroxymethyl)-1-{[(1E)-(5-nitro-2-furyl)
methylene]amino}imidazolidine-2,4-dione

CAS Number

1088-92-2^Y

PubChem CID

9571062

ChemSpider

7845528^N

UNII

980688H13O

KEGG

D07243^Y

ChEBI

CHEBI:88255^N

CompTox Dashboard (EPA)

DTXSID30148747

ECHA InfoCard100.012.842

Chemical and physical dataFormulaC₉H₈N₄O₆Molar mass268.185 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C1C(=O)N(C(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-])CO

InChI

InChI=1S/C9H8N4O6/c14-5-11-7(15)4-12(9(11)16)10-3-6-1-2-8(19-6)13(17)18/h1-3,14H,4-5H2/b10-3+^N
Key:UIDWQGRXEVDFCA-XCVCLJGOSA-N^N

^NY (what is this?) (verify)

Nifurtoinol (rINN, trade name Urfadyn) is a nitrofuran-derivative antibiotic used in the treatment of urinary tract infections.^{[citation needed]}

It is also known as "hydroxymethylnitrofurantoin".^[1]

References

^ Stricker BH, Blok AP, Claas FH, Van Parys GE, Desmet VJ (1988). "Hepatic injury associated with the use of nitrofurans: a clinicopathological study of 52 reported cases". Hepatology. 8 (3): 599–606. doi:10.1002/hep.1840080327. PMID 3371877.

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Brodimoprim
- Iclaprim^†
- Ormetoprim
- Pyrimethamine^#
- Tetroxoprim
- Trimethoprim^#

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Trimethoprim/sulfamethoxazole^#
Ormetoprim/sulfadimethoxine
Pyrimethamine/dapsone
Pyrimethamine/sulfadoxine

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Fluoroquinolones

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡/Levonadifloxacin/Alalevonadifloxacin Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡
3rd generation	Levofloxacin^# Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin^# Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin^‡

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Metronidazole^# Ornidazole Secnidazole Tinidazole
Nitrofuran derivatives	Furazolidone^‡ Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin^# Nitrofurazone