Olaflur (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...

, or amine fluoride 297) is a

fluoride Fluoride (). According to this source, is a possible pronunciation in British English. is an inorganic, monatomic anion of fluorine, with the chemical formula (also written ), whose salts are typically white or colorless. Fluoride salts typ ...

-containing substance that is an ingredient of toothpastes and solutions for the prevention of

dental caries Tooth decay, also known as cavities or caries, is the breakdown of teeth due to acids produced by bacteria. The cavities may be a number of different colors from yellow to black. Symptoms may include pain and difficulty with eating. Complicatio ...

. It has been in use since 1966. Especially in combination with

dectaflur Dectaflur (INN) is a fluoride-containing substance used for the prevention and treatment of dental caries, sensitive teeth, and the refluoridation of damaged tooth enamel, typically in combination with olaflur. Chemistry and mechanism of action ...

, it is also used in the form of gels for the treatment of early stages of caries, sensitive

teeth A tooth ( : teeth) is a hard, calcified structure found in the jaws (or mouths) of many vertebrates and used to break down food. Some animals, particularly carnivores and omnivores, also use teeth to help with capturing or wounding prey, tear ...

, and by

dentist A dentist, also known as a dental surgeon, is a health care professional who specializes in dentistry (the diagnosis, prevention, management, and treatment of diseases and conditions of the mouth, oral cavity and other aspects of the craniofaci ...

s for the refluoridation of damaged

tooth enamel Tooth enamel is one of the four major Tissue (biology), tissues that make up the tooth in humans and many other animals, including some species of fish. It makes up the normally visible part of the tooth, covering the Crown (tooth), crown. The ...

Overdosage

Overdosage leads to irritation of the

oral mucosa The oral mucosa is the mucous membrane lining the inside of the mouth. It comprises stratified squamous epithelium, termed "oral epithelium", and an underlying connective tissue termed ''lamina propria''. The oral cavity has sometimes been descri ...

. In especially sensitive persons, even standard doses of olaflur can cause irritation. 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 the

permanent teeth Permanent teeth or adult teeth are the second set of teeth formed in diphyodont mammals. In humans and old world simians, there are thirty-two permanent teeth, consisting of six maxillary and six mandibular molars, four maxillary and four mandibul ...

, overdosage can lead to

dental fluorosis Dental fluorosis is a common disorder, characterized by hypomineralization of tooth enamel caused by ingestion of excessive fluoride during enamel formation. It appears as a range of visual changes in enamel causing degrees of intrinsic tooth d ...

, a discolouring and weakening of the enamel. In acute cases of overdosage, for example when an olaflur containing preparation is swallowed, calcium in any oral form serves as an

antidote An antidote is a substance that can counteract a form of poisoning. The term ultimately derives from the Greek term φάρμακον ἀντίδοτον ''(pharmakon) antidoton'', "(medicine) given as a remedy". Antidotes for anticoagulants are s ...

. Often milk is used because it is usually at hand.

Interactions

Because

calcium fluoride Calcium fluoride is the inorganic compound of the elements calcium and fluorine with the formula CaF2. It is a white insoluble solid. It occurs as the mineral fluorite (also called fluorspar), which is often deeply coloured owing to impurities. ...

is practically insoluble in water, calcium-containing drugs and food inhibit the action of olaflur.

Chemistry and mechanism of action

Olaflur is a salt consisting of an alkyl ammonium cation and fluoride as the

counterion 160px, Polystyrene sulfonate, a cation-exchange resin, is typically supplied with as the counterion.">cation-exchange_resin.html" ;"title="Polystyrene sulfonate, a cation-exchange resin">Polystyrene sulfonate, a cation-exchange resin, is typical ...

. With a long

lipophilic Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipop ...

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...

chain, the cation has

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

properties. 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 Hydroxyapatite, also called hydroxylapatite (HA), is a naturally occurring mineral form of calcium apatite with the formula Ca5(PO4)3(OH), but it is usually written Ca10(PO4)6(OH)2 to denote that the crystal unit cell comprises two entities. ...

, are converted into the more robust

fluorapatite Fluorapatite, often with the alternate spelling of fluoroapatite, is a phosphate mineral with the formula Ca5(PO4)3F (calcium fluorophosphate). Fluorapatite is a hard crystalline solid. Although samples can have various color (green, brown, bl ...

. The fluoridation reaches only a depth of a few

nanometre 330px, Different lengths as in respect to the molecular scale. The nanometre (international spelling as used by the International Bureau of Weights and Measures; SI symbol: nm) or nanometer (American and British English spelling differences#-re ...

s, which has raised doubts whether the mechanism really relies on the formation of fluorapatite.

Synthesis

The synthesis of olaflur starts from cattle's

tallow Tallow is a rendering (industrial), rendered form of beef or mutton fat, primarily made up of triglycerides. In industry, tallow is not strictly defined as beef or mutton fat. In this context, tallow is animal fat that conforms to certain techn ...

. The contained

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

s, mainly

stearic acid Stearic acid ( , ) is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "''stéar''", which means tallow. ...

(C₁₇H₃₅COOH), are obtained by

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

, and then converted to the corresponding

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...

s, which in turn are reduced catalytically to the

primary amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such a ...

s (largely octadecylamine). Addition of

acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular ...

, followed by another reduction, yields ''N''-alkyl-1,3-propanediamines. The two nitrogen atoms react with

ethylene oxide Ethylene oxide is an organic compound with the chemical formula, formula . It is a cyclic ether and the simplest epoxide: a three-membered Ring (chemistry), ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless a ...

to form tertiary amines. Finally,

hydrofluoric acid Hydrofluoric acid is a Solution (chemistry), solution of hydrogen fluoride (HF) in water. Solutions of HF are colourless, acidic and highly Corrosive substance, corrosive. It is used to make most fluorine-containing compounds; examples include th ...

is 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 hydroxyethyl

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

s resulting from addition of ethylene oxide to the free hydroxyl groups. The presence of these side products is clinically irrelevant.

References

{{Stomatological preparations Dental materials Fluorides Amines Cationic surfactants

Overdosage

Interactions

Chemistry and mechanism of action

Synthesis

See also

References