Furaltadone
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| Identifiers | |
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| ECHA InfoCard | 100.004.895 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C13H16N4O6 | |
| Molar mass | 324.29 g·mol−1 |
| Appearance | yellow solid[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Furaltadone is a chemical compound from the group of nitrofurans, as it contains a 5-nitrofuran ring. Furaltadone is classified as a synthetic antibiotic. It was patented in 1957.[2]
Properties
[edit]Furaltadone has a chiral carbon atom and exists as a racemate. The (S)-form is known as levofuraltadone.[3]
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Furaltadone, (R) form -
Levofuraltadone, (S) form
Use
[edit]
Furaltadone was particularly used for the treatment of poultry. Residues of this active substance are classified as hazardous at any concentration due to their potential carcinogenic and mutagenic effects.[4]
Furaltadone is used in human medicine as an antibiotic for urinary tract infections.[5] It is also utilized as an antiprotozoal.[1] It was first introduced in October 1958 by Kefauver, Paberzs, and McNamara under the active ingredient name "Furmethonol" as a potentially effective agent for the peroral treatment of systemic bacterial infections.[6] It was introduced to the US market in 1959 under the trade name Altafur (Eaton Laboratories).[7]
Regulation
[edit]In the European Union, the use of furaltadone in food-producing animals has been banned since 1993. Consequently, no preparation based on this active substance is marketable.[4]
Under The Safe Drinking Water and Toxic Enforcement Act of 1986, California has required labeling for products containing furaltadone since April 1, 1988.[8]
References
[edit]- ^ a b J. Elks (2014), The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies, Springer, ISBN 978-1-4757-2085-3
- ^ US 2802002, "Series of new nu-(5-nitro-2-furyl) alkylidene-3-amino-5-tertiaryamino-methyl-2-oxazolidones and the preparation thereof", published 1957-08-06, assigned to Norwich Pharmacal Company
- ^ INN Recommended List 07, Weltgesundheitsorganisation (WHO), 9 December 1967.
- ^ a b Gesundheitliche Bewertung von Nitrofuranen in Lebensmitteln. Stellungnahme des BgVV 15 July 2002. Retrieved 4 August 2024.
- ^ G. W. A. Milne (2002), [[1], p. 762, at Google Books Drugs: Synonyms and Properties], Wiley, p. 762, ISBN 978-0-566-08491-1
{{citation}}: Check|url=value (help) - ^ Furaltadone - Antibacterial Activity in Vitro and in Serum of Patients During Treatment, doi:10.1001/archinte.1961.03620060063008, retrieved 2024-08-03
- ^ Furaltadone, National Center for Advancing Translational Sciences (NCATS), retrieved 12 August 2024.
- ^ "5-(Morpholinomethyl)-3-[(5-nitrofurfurylidene)-amino]-2-oxazolidinone". OEHHA. 1988-04-01. Retrieved 2024-08-05.