Olaflur
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| Other names | {3-[Octadecyl(2-hydroxyethyl)aminio]propyl}bis(2-hydroxyethyl)amine dihydrofluoride |
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| Routes of administration | Topical(toothpaste,mouthwash,gel) |
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| ECHA InfoCard | 100.027.174 |
| Chemical and physical data | |
| Formula | C27H60F2N2O3 |
| Molar mass | 498.785g·mol−1 |
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Olaflur(INN,oramine fluoride 297) is afluoride-containing substance that is an ingredient of toothpastes and solutions for the prevention ofdental caries.[1]It has been in use since 1966. Especially in combination withdectaflur,it is also used in the form of gels for the treatment of early stages of caries, sensitiveteeth,and bydentistsfor the refluoridation of damagedtooth enamel.[2]
Overdosage
[edit]Overdosage leads to irritation of theoral mucosa.In especially sensitive persons, even standard doses of olaflur can cause irritation.[2]Like other fluoride salts, olaflur is toxic when given in high doses over an extended period of time. Especially in children, before the development of thepermanent teeth,overdosage can lead todental fluorosis,a discolouring and weakening of the enamel.[3]In acute cases of overdosage, for example when an olaflur containing preparation is swallowed, calcium in any oral form serves as anantidote.Often milk is used because it is usually at hand.[2]
Interactions
[edit]Becausecalcium fluorideis practically insoluble in water, calcium-containing drugs and food inhibit the action of olaflur.[2]
Chemistry and mechanism of action
[edit]Olaflur is a salt consisting of analkyl ammoniumcation and fluoride as thecounterion.With a longlipophilichydrocarbonchain, the cation hassurfactantproperties. It forms a film layer on the surface of teeth, which facilitates incorporation of fluoride into the enamel. The top layers of the enamel's primary mineral,hydroxylapatite,are converted into the more robustfluorapatite.The fluoridation reaches only a depth of a fewnanometres,which has raised doubts whether the mechanism really relies on the formation of fluorapatite.[4]
Synthesis
[edit]The synthesis of olaflur starts from cattle'stallow.[5]The containedfatty acids,mainlystearic acid(C17H35COOH), are obtained byhydrolysis,and then converted to the correspondingamides,which in turn arereducedcatalytically to theprimary amines(largely octadecylamine). Addition ofacrylonitrile,followed by another reduction, yieldsN-alkyl-1,3-propanediamines. The two nitrogen atoms react withethylene oxideto form tertiary amines. Finally,hydrofluoric acidis added to give the end product. Because olaflur is produced from a mixture of fatty acids, some molecules have side chains that are longer or shorter than 18 carbon atoms. Other byproducts of the reaction include hydroxyethylethersresulting from addition of ethylene oxide to the free hydroxyl groups. The presence of these side products is clinically irrelevant.[5]
See also
[edit]References
[edit]- ^Ganss C, Klimek J, Brune V, Schürmann A (2004). "Effects of two fluoridation measures on erosion progression in human enamel and dentine in situ".Caries Research.38(6): 561–6.doi:10.1159/000080587.PMID15528912.S2CID12683542.
- ^abcdHaberfeld H, ed. (2009).Austria-Codex(in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag.ISBN978-3-85200-196-8.
- ^Abanto Alvarez J, Rezende KM, Marocho SM, Alves FB, Celiberti P, Ciamponi AL (February 2009). "Dental fluorosis: exposure, prevention and management".Medicina Oral, Patologia Oral y Cirugia Bucal.14(2): E103-7.PMID19179949.
- ^Müller F, Zeitz C, Mantz H, Ehses KH, Soldera F, Schmauch J, et al. (December 2010). "Elemental depth profiling of fluoridated hydroxyapatite: saving your dentition by the skin of your teeth?".Langmuir.26(24): 18750–9.doi:10.1021/la102325e.PMID21090577.
- ^abUS patent 6464962,Heckendorn R, Gosteli J, "N-Alkyldiethanolamine hydrofluorides and oral hygiene compositions containing them", published 2001-07-05, assigned to GABA International AG