Butyl cyanoacrylate
Encyclopedia
n-Butyl cyanoacrylate a cyanoacrylate
ester
, is a butyl ester
of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. It is insoluble in water. Its chief use is as the main component of medical cyanoacrylate glues. It can be encountered under various trade name
s, e.g. PeriAcryl, GluStitch, Xoin, Gesika, VetGlu, Vetbond, LiquiVet, Indermil, LiquiBand®, Histoacryl, and others.
n-butyl-2-cyanoacrylate or butyl cyanoacrylate is also known as Enbucrilate.
In medical and veterinary applications, n-butyl cyanoacrylate, isobutyl cyanoacrylate
, and octyl cyanoacrylate
are commonly used. They are bacteriostatic and their use is usually painless. Butyl esters provide stronger bond, but are rigid. Octyl ester, while providing weaker bond, are more flexible. n-Butyl cyanoacrylate is also used for embolization of cerebral arteriovenous malformations before their surgical treatment.
It is soluble in acetone
, methyl ethyl ketone, nitromethane
, and methylene chloride.
Butyl cyanoacrylate (in monomer form) polymerizes rapidly in presence of ionic substances like moisture, blood or tissue fluids.
Butyl cyanoacrylate has unique properties compared to other cyanoacrylates like octyl cyanoacryalte or iso amyl cyanoacrylate. Polymerized form has excellent tensile strength and is very effective in closing surgical or wound incisions.
The closure of the wound or cut is quick (about 30 to 45 seconds) and the product has inherently some valuable bacteriostatic properties. The cosmetic outcome of the closure is comparable or generally better than an equivalent suture substitute with least amount of scarring visible after three to six months. (Ref needed)
Also important is the in the body degradation properties of polymerized butyl cyanoacrylate. This property of butyl cyanaocrylate has made it a very useful polymer to create various nano particles for delivery of drugs into the body with sustained release profiles.
Heating to higher temperatures causes pyrolysis and depolymerization of the cured glue, producing gaseous products strongly irritant to lungs and eyes.
s by application of the glue into the abnormality through angiography.
In gastroenterology, butyl cyanoacrylate is used to treat bleeding gastric varices
, which are dilated vein
s that occur in the setting of liver cirrhosis
or thrombosis
of the splenic vein
. The gastric varices are accessed by endoscopy
, which uses a flexible fibre-optic camera to enter the stomach. They are injected with a catheter needle inserted into the varix through the endoscope. Other sites of varices, including esophageal varices
, duodenal varices
and colonic varices
. Gastric varices have also been obliterated with recurrent injection treatment with butyl cyanoacrylate.
Cyanoacrylate
Cyanoacrylate is the generic name for cyanoacrylate based fast-acting adhesives such as methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate , and n-butyl cyanoacrylate...
ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
, is a butyl ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. It is insoluble in water. Its chief use is as the main component of medical cyanoacrylate glues. It can be encountered under various trade name
Trade name
A trade name, also known as a trading name or a business name, is the name which a business trades under for commercial purposes, although its registered, legal name, used for contracts and other formal situations, may be another....
s, e.g. PeriAcryl, GluStitch, Xoin, Gesika, VetGlu, Vetbond, LiquiVet, Indermil, LiquiBand®, Histoacryl, and others.
n-butyl-2-cyanoacrylate or butyl cyanoacrylate is also known as Enbucrilate.
In medical and veterinary applications, n-butyl cyanoacrylate, isobutyl cyanoacrylate
Isobutyl cyanoacrylate
Isobutyl cyanoacrylate is an isomer of butyl cyanoacrylate. It is used in medical procedures either to close incisions and lacerations without the use of sutures, or as an adjunct to strengthen the suturing. This use is possible because it is a bactericidal liquid monomer which, in thepresence of...
, and octyl cyanoacrylate
Octyl cyanoacrylate
Octyl cyanoacrylate , a cyanoacrylate ester, is an octyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. Its chief use is as the main component of medical cyanoacrylate glues...
are commonly used. They are bacteriostatic and their use is usually painless. Butyl esters provide stronger bond, but are rigid. Octyl ester, while providing weaker bond, are more flexible. n-Butyl cyanoacrylate is also used for embolization of cerebral arteriovenous malformations before their surgical treatment.
It is soluble in acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
, methyl ethyl ketone, nitromethane
Nitromethane
Nitromethane is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent...
, and methylene chloride.
Butyl cyanoacrylate (in monomer form) polymerizes rapidly in presence of ionic substances like moisture, blood or tissue fluids.
Butyl cyanoacrylate has unique properties compared to other cyanoacrylates like octyl cyanoacryalte or iso amyl cyanoacrylate. Polymerized form has excellent tensile strength and is very effective in closing surgical or wound incisions.
The closure of the wound or cut is quick (about 30 to 45 seconds) and the product has inherently some valuable bacteriostatic properties. The cosmetic outcome of the closure is comparable or generally better than an equivalent suture substitute with least amount of scarring visible after three to six months. (Ref needed)
Also important is the in the body degradation properties of polymerized butyl cyanoacrylate. This property of butyl cyanaocrylate has made it a very useful polymer to create various nano particles for delivery of drugs into the body with sustained release profiles.
Heating to higher temperatures causes pyrolysis and depolymerization of the cured glue, producing gaseous products strongly irritant to lungs and eyes.
Medical applications
The medical applications of butyl cyanoacrylate include its use as an adhesive for lacerations of the skin, and in the treatment of bleeding from vascular structures. Butyl cyanoacrylate has been used to treat arteriovenous malformationArteriovenous malformation
Arteriovenous malformation or AVM is an abnormal connection between veins and arteries, usually congenital. This pathology is widely known because of its occurrence in the central nervous system, but can appear in any location. An arteriovenous malformation is a vascular anomaly. It is a...
s by application of the glue into the abnormality through angiography.
In gastroenterology, butyl cyanoacrylate is used to treat bleeding gastric varices
Gastric varices
Gastric varices are dilated submucosal veins in the stomach, which can be a life-threatening cause of upper gastrointestinal hemorrhage. They are most commonly found in patients with portal hypertension, or elevated pressure in the portal vein system, which may be a complication of cirrhosis...
, which are dilated vein
Vein
In the circulatory system, veins are blood vessels that carry blood towards the heart. Most veins carry deoxygenated blood from the tissues back to the heart; exceptions are the pulmonary and umbilical veins, both of which carry oxygenated blood to the heart...
s that occur in the setting of liver cirrhosis
Cirrhosis
Cirrhosis is a consequence of chronic liver disease characterized by replacement of liver tissue by fibrosis, scar tissue and regenerative nodules , leading to loss of liver function...
or thrombosis
Thrombosis
Thrombosis is the formation of a blood clot inside a blood vessel, obstructing the flow of blood through the circulatory system. When a blood vessel is injured, the body uses platelets and fibrin to form a blood clot to prevent blood loss...
of the splenic vein
Splenic vein
In anatomy, the splenic vein is the blood vessel that drains blood from the spleen.It joins with the superior mesenteric vein, to form the hepatic portal vein and follows a course superior to the pancreas, alongside of the similarly named artery, the splenic artery.It collects branches from the...
. The gastric varices are accessed by endoscopy
Esophagogastroduodenoscopy
For other expansions of the initialism "OGD", see the disambiguation page.In medicine , esophagogastroduodenoscopy is a diagnostic endoscopic procedure that visualizes the upper part of the gastrointestinal tract up to the duodenum...
, which uses a flexible fibre-optic camera to enter the stomach. They are injected with a catheter needle inserted into the varix through the endoscope. Other sites of varices, including esophageal varices
Esophageal varices
In medicine , esophageal varices are extremely dilated sub-mucosal veins in the lower esophagus...
, duodenal varices
Duodenum
The duodenum is the first section of the small intestine in most higher vertebrates, including mammals, reptiles, and birds. In fish, the divisions of the small intestine are not as clear and the terms anterior intestine or proximal intestine may be used instead of duodenum...
and colonic varices
Colon (anatomy)
The colon is the last part of the digestive system in most vertebrates; it extracts water and salt from solid wastes before they are eliminated from the body, and is the site in which flora-aided fermentation of unabsorbed material occurs. Unlike the small intestine, the colon does not play a...
. Gastric varices have also been obliterated with recurrent injection treatment with butyl cyanoacrylate.
See also
- Isobutyl cyanoacrylateIsobutyl cyanoacrylateIsobutyl cyanoacrylate is an isomer of butyl cyanoacrylate. It is used in medical procedures either to close incisions and lacerations without the use of sutures, or as an adjunct to strengthen the suturing. This use is possible because it is a bactericidal liquid monomer which, in thepresence of...
- Methyl cyanoacrylateMethyl cyanoacrylateMethyl cyanoacrylate is an organic compound that contains several functional groups, a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues. It can be encountered under many trade names...
- Ethyl cyanoacrylateEthyl cyanoacrylateEthyl cyanoacrylate , a cyanoacrylate ester, is an ethyl ester of 2-cyano-2-propenoic acid. It is a colorless liquid with low viscosity. It is the main component of cyanoacrylate glues and can be encountered under many trade names. Super glue and Krazy glue are believed to be virtually 100% ECA...
- Octyl cyanoacrylateOctyl cyanoacrylateOctyl cyanoacrylate , a cyanoacrylate ester, is an octyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. Its chief use is as the main component of medical cyanoacrylate glues...