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furylfuramide
Sign in to saveAlso known as AF-2, 2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide, AF 2
Furylfuramide (also known as AF-2) is a synthetic nitrofuran derivative which was widely used as a food preservative in Japan since at least 1965, but withdrawn from the market in 1974 when it was observed to be mutagenic to bacteria in vitro and thus suspected of carcinogenicity. This was confirmed later when animal testing found it to cause benign and malignant tumors in the mammary glands, stomachs, esophagi, and lungs of rodents of both sexes, although insufficient evidence exists in human exposure.
Chemical data
- Formula
- C11H8N2O5
- Molecular weight
- 248.19 g/mol
- IUPAC name
- 2-(furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enamide
- SMILES
- C1=COC(=C1)C(=CC2=CC=C(O2)[N+](=O)[O-])C(=O)N
- InChIKey
- LYAHJFZLDZDIOH-UHFFFAOYSA-N
- XLogP
- 0.1
- Polar surface area
- 115 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
230 papers- AlphaFold2 and its applications in the fields of biology and medicine.Signal transduction and targeted therapy · 2023
- Mutagenicity of nitrofuran derivatives, including furylfuramide, a food preservative.Mutation research · 1975
- Toxicological significance of hepatic responses to furylfuramide(AF-2) in the rat.Toxicology · 1986
- Tertiary structure assessment at CASP15.Proteins · 2023
- Metabolic deactivation of furylfuramide by cytochrome P450 in human and rat liver microsomes.Carcinogenesis · 1990
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 248.043321
Show 5 more facts
- chemical formula
- C₁₁H₈N₂O₅
- canonical SMILES
- C1=COC(=C1)C(=CC2=CC=C(O2)[N+](=O)[O-])C(=O)N
- isomeric SMILES
- C1=COC(=C1)/C(=C/C2=CC=C(O2)[N+](=O)[O-])/C(=O)N
- subject has role
- carcinogen
- Commons category
- Furylfuramide
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Furylfuramide (also known as AF-2) is a synthetic nitrofuran derivative which was widely used as a food preservative in Japan since at least 1965, but withdrawn from the market in 1974 when it was observed to be mutagenic to bacteria in vitro and thus suspected of carcinogenicity. This was confirmed later when animal testing found it to cause benign and malignant tumors in the mammary glands, stomachs, esophagi, and lungs of rodents of both sexes, although insufficient evidence exists in human exposure.
This successful use of bacterial mutagenicity as a screen for carcinogenicity confirmed the use of this methodology as a rapid and efficient test, in comparison to animal testing alone, and led to its further development. The availability of such simpler tests in turn gave rise to greater government oversight and testing of compounds to which the public would be exposed.
Excerpted from Wikipedia’s “furylfuramide” article, available under the CC BY-SA 4.0 licence.