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 accomm ...

, or amine fluoride 297) is a

fluoride Fluoride (). According to this source, is a possible pronunciation in British English. is an Inorganic chemistry, inorganic, Monatomic ion, monatomic Ion#Anions and cations, anion of fluorine, with the chemical formula (also written ), whose ...

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

dental caries Tooth decay, also known as caries,The word 'caries' is a mass noun, and is not a plural of 'carie'.'' is the breakdown of teeth due to acids produced by bacteria. The resulting cavities may be a number of different colors, from yellow to black ...

. It has been in use since 1966. Especially in combination with dectaflur, 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 doctor, dental physician, dental surgeon, is a health care professional who specializes in dentistry, the branch of medicine focused on the teeth, gums, and mouth. The dentist's supporting team aids in provi ...

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 animals, including some species of fish. It makes up the normally visible part of the tooth, covering the Crown (tooth), crown. The other ...

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 des ...

. 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 mandib ...

, overdosage can lead to

dental fluorosis Dental fluorosis is a common disorder, characterized by Enamel hypocalcification, hypocalcification of tooth enamel caused by ingestion of excessive fluoride during enamel formation. Dental fluorosis appears as a range of visual changes in ename ...

, 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". An older term in English which is ...

. 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 solid that is practically insoluble in water. It occurs as the mineral fluorite (also called fluorspar), which is often deeply col ...

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, cation-exchange_resin.html" ;"title="Polystyrene sulfonate, a cation-exchange resin">Polystyrene sulfonate, a cation-exchange resin, is typically supplied with as the counterion. In chemistry, a counterion (sometimes written as "counter ...

. With a long

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

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 Hydrophobe, hydrophobic; their odor is usually fain ...

chain, the cation has

surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

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 ( IMA name: hydroxylapatite) (Hap, HAp, or HA) is a naturally occurring mineral form of calcium apatite with the formula , often written to denote that the crystal unit cell comprises two entities. It is the hydroxyl endmembe ...

, 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, blu ...

. The fluoridation reaches only a depth of a few

nanometre 330px, Different lengths as in respect to the Molecule">molecular scale. The nanometre (international spelling as used by the International Bureau of Weights and Measures; SI symbol: nm), or nanometer (American spelling), is a unit of length ...

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 rendered form of beef or mutton suet, primarily made up of triglycerides. In industry, tallow is not strictly defined as beef or mutton suet. In this context, tallow is animal fat that conforms to certain technical criteria, inc ...

. The contained

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

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 soft waxy solid with the formula . The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid ...

(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 chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...

s, which in turn are

reduced Reduction, reduced, or reduce may refer to: Science and technology Chemistry * Reduction (chemistry), part of a reduction-oxidation (redox) reaction in which atoms have their oxidation state changed. ** Organic redox reaction, a redox reacti ...

catalytically to the

primary amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

s (largely octadecylamine). Addition of

acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group () linked to a nitrile (). It is an im ...

, 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 ...

to form tertiary amines. Finally,

hydrofluoric acid Hydrofluoric acid is a solution of hydrogen fluoride (HF) in water. Solutions of HF are colorless, acidic and highly corrosive. A common concentration is 49% (48–52%) but there are also stronger solutions (e.g. 70%) and pure HF has a boiling p ...

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, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

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 Ammonium compounds Cationic surfactants

Overdosage

Interactions

Chemistry and mechanism of action

Synthesis

See also

References