Olaflur is a fluoride

Fluoride

Fluoride is the anion F−, the reduced form of fluorine when as an ion and when bonded to another element. Both organofluorine compounds and inorganic fluorine containing compounds are called fluorides. Fluoride, like other halides, is a monovalent ion . Its compounds often have properties that are...

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

Dental caries

Dental caries, also known as tooth decay or a cavity, is an irreversible infection usually bacterial in origin that causes demineralization of the hard tissues and destruction of the organic matter of the tooth, usually by production of acid by hydrolysis of the food debris accumulated on the...

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

Dectaflur

Dectaflur 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, and by dentist

Dentist

A dentist, also known as a 'dental surgeon', is a doctor that specializes in the diagnosis, prevention, and treatment of diseases and conditions of the oral cavity. The dentist's supporting team aides in providing oral health services...

s for the refluoridation of damaged tooth enamel

Tooth enamel

Tooth enamel, along with dentin, cementum, and dental pulp is one of the four major tissues that make up the tooth in vertebrates. It is the hardest and most highly mineralized substance in the human body. Tooth enamel is also found in the dermal denticles of sharks...

.

Overdosage

Overdosage leads to irritation of the oral mucosa

Oral mucosa

The oral mucosa is the mucous membrane epithelium of the mouth. It can be divided into three categories.*Masticatory mucosa, para-keratinized stratified squamous epithelium, found on the dorsum of the tongue, hard palate and attached gingiva....

. 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

Permanent teeth are the second set of teeth formed in humans. There are thirty-two permanent teeth, consisting of six maxillary and six mandibular molars, four maxillary and four mandibular premolars, two maxillary and two mandibular canines, four maxillary and four mandibular incisors.The first...

, overdosage can lead to dental fluorosis

Dental fluorosis

Dental fluorosis is a developmental disturbance of dental enamel caused by excessive exposure to high concentrations of fluoride during tooth development. The risk of fluoride overexposure occurs between the ages of 3 months and 8 years. In its mild forms , fluorosis often appears as unnoticeable,...

, 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

Antidote

An antidote is a substance which can counteract a form of poisoning. The term ultimately derives from the Greek αντιδιδοναι antididonai, "given against"....

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

Interactions

Because calcium fluoride

Calcium fluoride

Calcium fluoride is the inorganic compound with the formula CaF2. This ionic compound of calcium and fluorine occurs naturally as the mineral fluorite . It is the source of most of the world's fluorine. This insoluble solid adopts a cubic structure wherein calcium is coordinated to eight fluoride...

 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

Amine

Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...

 cation and fluoride as the counterion

Counterion

A counterion is the ion that accompanies an ionic species in order to maintain electric neutrality. In table salt the sodium cation is the counterion for the chlorine anion and vice versa.In a charged transition metal complex, a simple A counterion is the ion that accompanies an ionic species in...

. With a long lipophilic

Lipophilic

Lipophilicity, , refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. These non-polar solvents are themselves lipophilic — the axiom that like dissolves like generally holds true...

 hydrocarbon

Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....

 chain, the cation has surfactant

Surfactant

Surfactants are compounds that lower the surface tension of a liquid, the interfacial tension between two liquids, or that between a liquid and a solid...

 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

Hydroxylapatite

Hydroxylapatite, also called hydroxyapatite , is a naturally occurring mineral form of calcium apatite with the formula Ca53, but is usually written Ca1062 to denote that the crystal unit cell comprises two entities. Hydroxylapatite is the hydroxyl endmember of the complex apatite group...

, are converted into the more robust fluorapatite

Fluorapatite

Fluorapatite, often with the alternate spelling of fluoroapatite, is a mineral with the formula Ca53F . Fluorapatite is a hard crystalline solid. Although samples can have various color , the pure mineral is colorless as expected for a material lacking transition metals...

. The fluoridation reaches only a depth of a few nanometre

Nanometre

A nanometre is a unit of length in the metric system, equal to one billionth of a metre. The name combines the SI prefix nano- with the parent unit name metre .The nanometre is often used to express dimensions on the atomic scale: the diameter...

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

Tallow is a rendered form of beef or mutton fat, processed from suet. It is solid at room temperature. Unlike suet, tallow can be stored for extended periods without the need for refrigeration to prevent decomposition, provided it is kept in an airtight container to prevent oxidation.In industry,...

. The contained fatty acid

Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid with a long unbranched aliphatic tail , which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually derived from...

s, mainly stearic acid

Stearic acid

Stearic acid is the saturated fatty acid with an 18 carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid, and its chemical formula is CH316CO2H. Its name comes from the Greek word στέαρ "stéatos", which means tallow. The salts and esters of stearic acid are called stearates...

 (C₁₈H₃₇COOH), are obtained by hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

, and then converted to the corresponding amide

Amide

In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...

s, which in turn are reduced catalytically to the primary amines. Addition of acrylonitrile

Acrylonitrile

Acrylonitrile is the chemical compound with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile...

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

Ethylene oxide

Ethylene oxide, also called oxirane, is the organic compound with the formula . It is a cyclic ether. This means that it is composed of two alkyl groups attached to an oxygen atom in a cyclic shape . This colorless flammable gas with a faintly sweet odor is the simplest epoxide, a three-membered...

 (oxirane) to tertiary amines. Finally, hydrofluoric acid

Hydrofluoric acid

Hydrofluoric acid is a solution of hydrogen fluoride in water. It is a valued source of fluorine and is the precursor to numerous pharmaceuticals such as fluoxetine and diverse materials such as PTFE ....

 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

Ether

Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...

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