Etidronic acid, also known as etidronate, is a
bisphosphonate
Bisphosphonates are a class of drugs that prevent the loss of bone density, used to treat osteoporosis and similar diseases. They are the most commonly prescribed to treat osteoporosis.
Evidence shows that they reduce the risk of fracture in ...
drug. It is non-nitrogenous bisphosphonate. It was patented in 1966 and approved for medical use in 1977.
For medicinal purposes, etidronic acid has been obsolete since the early 2010's.
Use
Medical
Etidronic acid is a bisphosphonate once used to strengthen
bone
A bone is a rigid organ that constitutes part of the skeleton in most vertebrate animals. Bones protect the various other organs of the body, produce red and white blood cells, store minerals, provide structure and support for the body, ...
, treat
osteoporosis
Osteoporosis is a systemic skeletal disorder characterized by low bone mass, micro-architectural deterioration of bone tissue leading to more porous bone, and consequent increase in Bone fracture, fracture risk.
It is the most common reason f ...
, and treat
Paget's disease of bone
Paget's disease of bone (commonly known as Paget's disease or, historically, osteitis deformans) is a condition involving Bone remodeling, cellular remodeling and deformity of one or more bones. The affected bones show signs of dysregulated bone ...
.
Bisphosphonates primarily reduce
osteoclast
An osteoclast () is a type of bone cell that breaks down bone tissue. This function is critical in the maintenance, repair, and bone remodeling, remodeling of bones of the vertebrate, vertebral skeleton. The osteoclast disassembles and digests th ...
ic activity, which prevents
bone resorption
Bone resorption is resorption of bone tissue, that is, the process by which osteoclasts break down the tissue in bones and release the minerals, resulting in a transfer of calcium from bone tissue to the blood.
The osteoclasts are multi-nuclea ...
, and thus moves the bone resorption/formation equilibrium toward the formation side and hence makes bone denser in the long run. Etidronate, unlike other bisphosphonates, also prevents bone
calcification
Calcification is the accumulation of calcium salts in a body tissue. It normally occurs in the formation of bone, but calcium can be deposited abnormally in soft tissue,Miller, J. D. Cardiovascular calcification: Orbicular origins. ''Nature M ...
. For this reason, other bisphosphonates, such as
alendronate
Alendronic acid, sold under the brand name Fosamax among others, is a bisphosphonate medication used to treat osteoporosis and Paget's disease of bone. It is taken by mouth. Use is often recommended together with vitamin D, calcium supplementa ...
, are preferred when fighting osteoporosis. To prevent bone resorption without affecting too much bone calcification, etidronate is administered only for a short time once in a while, for example for two weeks every 3 months. When given on a continuous basis, say every day, etidronate will altogether prevent bone calcification. This effect may be useful and etidronate was in fact used this way to fight
heterotopic ossification
Heterotopic ossification (HO) is the process by which bone tissue forms Heterotopia (medicine), outside of the skeleton in muscles and soft tissue.
Symptoms
In traumatic heterotopic ossification (traumatic myositis ossificans), the patient may ...
. But in the long run, if used on a continuous basis, it will cause
osteomalacia
Osteomalacia is a disease characterized by the softening of the bones caused by impaired bone metabolism primarily due to inadequate levels of available phosphate, calcium, and vitamin D, or because of resorption of calcium. The impairment of b ...
.
Chemical
HEDP is a versatile phosphonate compound known for its
corrosion inhibition,
chelating
Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...
, and stabilizing properties, making it valuable across a range of industrial and consumer applications.
In industrial contexts, HEDP acts as a retardant of
cement hydration in concrete, extending the dormant period before hardening begins. It is also used as a scale and corrosion inhibitor in circulating cooling water systems,
oil fields
A petroleum reservoir or oil and gas reservoir is a subsurface accumulation of hydrocarbons contained in porous or fractured rock formations. Such reservoirs form when kerogen (ancient plant matter) is created in surrounding rock by the presen ...
, and low-pressure boilers, serving industries such as electric power, chemical manufacturing,
metallurgy
Metallurgy is a domain of materials science and engineering that studies the physical and chemical behavior of metallic elements, their inter-metallic compounds, and their mixtures, which are known as alloys.
Metallurgy encompasses both the ...
, and fertilizer production.
Beyond these applications, HEDP is utilized in the
dyeing
Dyeing is the application of dyes or pigments on textile materials such as fibers, yarns, and fabrics with the goal of achieving color with desired color fastness. Dyeing is normally done in a special solution containing dyes and particular ...
industry as a
peroxide
In chemistry, peroxides are a group of Chemical compound, compounds with the structure , where the R's represent a radical (a portion of a complete molecule; not necessarily a free radical) and O's are single oxygen atoms. Oxygen atoms are joined ...
stabilizer and dye-fixing agent, and in non-cyanide
electroplating
Electroplating, also known as electrochemical deposition or electrodeposition, is a process for producing a metal coating on a solid substrate through the redox, reduction of cations of that metal by means of a direct current, direct electric cur ...
where it functions as a chelating agent. In the light woven industry, it serves as a detergent for cleaning metal and non-metal surfaces and is often combined with
polycarboxylic acids (superplasticizers) as a reducing agent. Typical dosages range from 1–10 mg/L for scale inhibition, 10–50 mg/L for corrosion inhibition, and 1000–2000 mg/L for detergent use.
As a chelating agent, HEDP binds to calcium, iron, and other metal ions, helping to reduce their potential environmental impact, particularly through
greywater
Greywater (or grey water, sullage, also spelled gray water in the United States) refers to domestic wastewater generated in households or office buildings from streams without fecal contamination, i.e., all streams except for the wastewater fro ...
discharge into
groundwater
Groundwater is the water present beneath Earth's surface in rock and Pore space in soil, soil pore spaces and in the fractures of stratum, rock formations. About 30 percent of all readily available fresh water in the world is groundwater. A unit ...
. Its phosphonate structure also imparts corrosion resistance to unalloyed steel, and it retards
rancidification
Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.
When these processes ...
and oxidation of
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.
In detergents and cleaning agents, HEDP and its salts help mitigate the adverse effects of
hard water
Hard water is water that has a high mineral content (in contrast with "soft water"). Hard water is formed when water percolates through deposits of limestone, chalk or gypsum, which are largely made up of calcium and magnesium carbonates, bic ...
and stabilize peroxides during
bleaching
Bleach is the generic name for any chemical product that is used industrially or domestically to remove color from (i.e. to whiten) fabric or fiber (in a process called bleaching) or to disinfect after cleaning. It often refers specifically t ...
by inhibiting degradation caused by
transition metal
In chemistry, a transition metal (or transition element) is a chemical element in the d-block of the periodic table (groups 3 to 12), though the elements of group 12 (and less often group 3) are sometimes excluded. The lanthanide and actinid ...
s. Within the cosmetics industry, HEDP is used as a radical formation suppressant,
emulsion
An emulsion is a mixture of two or more liquids that are normally Miscibility, immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloi ...
stabilizer, and viscosity control agent. Although approved for use in cosmetic products, it is recommended that products containing HEDP, particularly soaps, be thoroughly rinsed from the skin after use.
HEDP also finds application in swimming pool maintenance, where it functions as a stain inhibitor by preventing metal ions from precipitating and staining pool surfaces.
Pharmacology
Synthesis
Etidronic acid can be prepared by reactions of dialkylphosphites and
carboxylic acid anhydride
An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups chemical bond, bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhyd ...
s. Other precursors include
phosphorus trichloride
Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic ...
and
phosphorous acid
Phosphorous acid (or phosphonic acid) is the Compound (chemistry), compound described by the chemical formula, formula . It is diprotic (readily ionizes two protons), not triprotic as might be suggested by its formula. Phosphorous acid is an in ...
.
References
{{Bisphosphonates
Bisphosphonates
Chelating agents