Furaltadone

Furaltadone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.895 Edit this at Wikidata
EC Number
  • 205-384-5
KEGG
UNII
  • InChI=1S/C13H16N4O6/c18-13-16(14-7-10-1-2-12(22-10)17(19)20)9-11(23-13)8-15-3-5-21-6-4-15/h1-2,7,11H,3-6,8-9H2/b14-7+
    Key: YVQVOQKFMFRVGR-VGOFMYFVSA-N
  • C1COCCN1CC2CN(C(=O)O2)/N=C/C3=CC=C(O3)[N+](=O)[O-]
Properties
C13H16N4O6
Molar mass 324.29 g·mol−1
Appearance yellow solid[1]
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P317, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Furaltadone has a chiral carbon atom and exists as a racemate. The (S)-form is known as levofuraltadone.[3]

  • Furaltadone, (R) form
    Furaltadone, (R) form
  • Levofuraltadone, (S) form
    Levofuraltadone, (S) form

Use

furaltadone hydrochloride

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

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

  1. ^ a b J. Elks (2014), The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies, Springer, ISBN 978-1-4757-2085-3
  2. ^ 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 
  3. ^ INN Recommended List 07, Weltgesundheitsorganisation (WHO), 9 December 1967.
  4. ^ a b Gesundheitliche Bewertung von Nitrofuranen in Lebensmitteln. Stellungnahme des BgVV 15 July 2002. Retrieved 4 August 2024.
  5. ^ 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)
  6. ^ "Furaltadone - Antibacterial Activity in Vitro and in Serum of Patients During Treatment", Archives of Internal Medicine, vol. 107, no. 6, pp. 863–871, June 1961, doi:10.1001/archinte.1961.03620060063008, retrieved 2024-08-03
  7. ^ Furaltadone, National Center for Advancing Translational Sciences (NCATS), retrieved 12 August 2024.
  8. ^ "5-(Morpholinomethyl)-3-[(5-nitrofurfurylidene)-amino]-2-oxazolidinone". OEHHA. 1988-04-01. Retrieved 2024-08-05.