Page last updated: 2024-12-11

nifurtoinol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

nifurtoinol : 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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID9571062
CHEMBL ID1697763
CHEBI ID88255
SCHEMBL ID1649671
MeSH IDM0043633

Synonyms (40)

Synonym
nifurtoinolum [inn-latin]
nifurtoinol [inn]
3-(hydroxymethyl)-1-((5-nitrofurfurylidene)amino)hydantoin
3-(hydroxymethyl)-1-(5-nitrofurfurylideneamino)hydantoin
levantin
3-(hydroxymethyl)-1-(((5-nitro-2-furanyl)methylene)amino)-2,4-imidazolidinedione
hydroxymethylnitrofurantoin
2,4-imidazolidinedione, 3-(hydroxymethyl)-1-(((5-nitro-2-furanyl)methylene)amino)-
urfadin
hydantoin, 3-(hydroxymethyl)-1-((5-nitrofurfurylidene)amino)-
3-(hydroxymethyl)-1-(((5-nitro-2-furanyl)methylene)amino)2,4-imidazolidinedione
urfadyn
nifurtoinol
urfadine
brn 0897492
einecs 214-126-0
D07243
nifurtoinol (inn)
1088-92-2
urfadyn (tn)
CHEMBL1697763
nifurtoinolum
980688h13o ,
5-24-05-00230 (beilstein handbook reference)
unii-980688h13o
nifurtoinol [mart.]
nifurtoinol [who-dd]
nifurtoinol [mi]
AKOS016372191
SCHEMBL1649671
DTXSID30148747
CHEBI:88255
3-(hydroxymethyl)-1-{[(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione
3-(hydroxymethyl)-1-[[(e)-(5-nitro-2-furyl)methylidene]amino]-2,4-imidazolidinedione
3-hydroxymethyl-1-(5-nitrofurfurylideneamino)hydantoin
DB13730
3-(hydroxymethyl)-1-[(e)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
CS-0094988
HY-128502
3-(hydroxymethyl)-1-(((5-nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"This single-blind crossover study compared the human bioavailability of macrocrystalline nitrofurantoin (Furadantine MC) and two prolonged-action hydroxymethylnitrofurantoin formulations (Urfadyn PL, bid, and Uridurine, tid), based on plasma nitrofurantoin concentrations and urinary nitrofurantoin excretion."( Comparative human bioavailability study of macrocrystalline nitrofurantoin and two prolonged-action hydroxymethylnitrofurantoin preparations.
Boerema, JB; Guelen, PJ; Vree, TB, 1988
)
0.27

Dosage Studied

ExcerptRelevanceReference
" For comparison, Furadantine MC was administered both at the qid dosage recommended by the manufacturer and at tid dosage."( Comparative human bioavailability study of macrocrystalline nitrofurantoin and two prolonged-action hydroxymethylnitrofurantoin preparations.
Boerema, JB; Guelen, PJ; Vree, TB, 1988
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antiinfective agentA substance used in the prophylaxis or therapy of infectious diseases.
antibacterial drugA drug used to treat or prevent bacterial infections.
hepatotoxic agentA role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
nitrofuran antibioticA member of the class of furans in which the furan ring is substituted by a nitro group and which also has significant antibiotic properties.
imidazolidine-2,4-dioneAn imidazolidinone with oxo groups at position 2 and 4.
organonitrogen heterocyclic antibiotic
hydrazoneCompounds having the structure R2C=NNR2, formally derived from aldehydes or ketones by replacing =O by =NNH2 (or substituted analogues).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (85.71)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's1 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.32

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index26.32 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (26.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (10.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (10.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]