Nifurtoinol

Nifurtoinol
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	J01XE02 (WHO)
Pharmacokinetic data
Excretion	Renal (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
ECHA InfoCard	100.012.842
Chemical and physical data
Formula	C₉H₈N₄O₆
Molar mass	268.183 g/mol
3D 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.

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. PMID 3371877. doi:10.1002/hep.1840080327.

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

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea
Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole Sulfanitran

Combinations

Other DHPS inhibitors

Fluoro-
quinolones

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

Newer non-fluorinated

Related (DG)

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole
Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin^# Rifapentine^# Rifaximin Rifalazil^§

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