Butyl cyanoacrylate

Last updated
n-Butyl cyanoacrylate
Butyl-cyanoacrylate-2D-skeletal.svg
Butyl cyanoacrylate 3D spacefill.png
Names
Preferred IUPAC name
Butyl 2-cyanoprop-2-enoate
Other names
Butyl 2-cyanopropenoate
Butyl 2-cyanoacrylate
2-Cyano-2-propenoic acid n-butyl ester
n-Butyl 2-cyanoacrylate
n-BCA
NBCA
n-Butyl alpha-cyanoacrylate
Enbucrilate (INN)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.026.866 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 229-552-2
PubChem CID
UNII
  • InChI=1/C8H11NO2/c1-3-4-5-11-8(10)7(2)6-9/h2-5H2,1H3
    Key: JJJFUHOGVZWXNQ-UHFFFAOYAK
  • N#CC(=C)C(=O)OCCCC
Properties
C8H11NO2
Molar mass 153.181 g·mol−1
Density 0.986 g/cm3 at 20 °C [1]
Boiling point 69–72 °C (156–162 °F; 342–345 K) [1] at 1.6 mmHg
Hazards
Flash point >80 °C (176 °F; 353 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

n-Butyl cyanoacrylate (n-BCA, NBCA), a cyanoacrylate ester, is a butyl ester of 2-cyano-2-propenoic acid. It is a colorless liquid with a sharp, irritating odor. It is insoluble in water. Its chief use is as the main component of medical cyanoacrylate glues. [2] It can be encountered under various trade names, e.g. Cutseal, MediBond, MediCryl, PeriAcryl, GluStitch, Xoin, Gesika, VetGlu, Vetbond, LiquiVet, Indermil, LiquiBand, Histoacryl, IFABond, CutisSeal and others. [3] The generic international nonproprietary name (INN) for NBCA is enbucrilate.

Contents

In medical and veterinary applications, NBCA, 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 esters, while providing weaker bond, are more flexible. Blends of octyl cyanoacrylate and n-butyl cyanoacrylate are available (such as GLUture) which offer both flexibility and a strong bond. n-Butyl cyanoacrylate is also used for embolization of cerebral arteriovenous malformations before their surgical treatment. [2]

NBCA in monomer form is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride. [4] It polymerizes rapidly in presence of ionic substances such as moisture, blood, or tissue fluids.

NBCA has unique properties compared to other cyanoacrylates such as octyl cyanoacrylate or isoamyl cyanoacrylate. The 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.[ citation needed ]

Also important is the degradation properties of polymerized NBCA within the body. This property of NBCA has made it a very useful polymer to create various nanoparticles 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 irritating to lungs and eyes.

Medical applications

The medical applications of butyl cyanoacrylate include its use as an adhesive for lacerations of the skin, [5] and in the treatment of bleeding from vascular structures. Butyl cyanoacrylate has been used to treat arteriovenous malformations [6] by application of the glue into the abnormality through angiography.

In gastroenterology, butyl cyanoacrylate is used to treat bleeding gastric varices, which are dilated veins that occur in the setting of liver cirrhosis or thrombosis of the splenic vein. [7] 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, [8] duodenal varices [9] and colonic varices. [10] Gastric varices have also been obliterated with recurrent injection treatment with butyl cyanoacrylate. [11]

See also

Related Research Articles

<span class="mw-page-title-main">Arteriovenous malformation</span> Vascular anomaly

An arteriovenous malformation (AVM) is an abnormal connection between arteries and veins, bypassing the capillary system. Usually congenital, this vascular anomaly is widely known because of its occurrence in the central nervous system, but can appear anywhere in the body. The symptoms of AVMs can range from none at all to intense pain or bleeding, and they can lead to other serious medical problems.

<span class="mw-page-title-main">Cyanoacrylate</span> Type of fast-acting adhesive

Cyanoacrylates are a family of strong fast-acting adhesives with industrial, medical, and household uses. They are derived from ethyl cyanoacrylate and related esters. The cyanoacrylate group in the monomer rapidly polymerizes in the presence of water to form long, strong chains.

Acrylates are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH2=CHCO−2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.

<span class="mw-page-title-main">Upper gastrointestinal bleeding</span> Medical condition

Upper gastrointestinal bleeding is gastrointestinal bleeding (hemorrhage) in the upper gastrointestinal tract, commonly defined as bleeding arising from the esophagus, stomach, or duodenum. Blood may be observed in vomit or in altered form as black stool. Depending on the amount of the blood loss, symptoms may include shock.

Coffee ground vomitus refers to a particular appearance of vomit. Within organic heme molecules of red blood cells is the element iron, which oxidizes following exposure to gastric acid. This reaction causes the vomitus to look like ground coffee.

<span class="mw-page-title-main">Esophageal varices</span> Medical condition

Esophageal varices are extremely dilated sub-mucosal veins in the lower third of the esophagus. They are most often a consequence of portal hypertension, commonly due to cirrhosis. People with esophageal varices have a strong tendency to develop severe bleeding which left untreated can be fatal. Esophageal varices are typically diagnosed through an esophagogastroduodenoscopy.

<span class="mw-page-title-main">Gastrointestinal bleeding</span> Medical condition

Gastrointestinal bleeding, also called gastrointestinal hemorrhage (GIB), is all forms of bleeding in the gastrointestinal tract, from the mouth to the rectum. When there is significant blood loss over a short time, symptoms may include vomiting red blood, vomiting black blood, bloody stool, or black stool. Small amounts of bleeding over a long time may cause iron-deficiency anemia resulting in feeling tired or heart-related chest pain. Other symptoms may include abdominal pain, shortness of breath, pale skin, or passing out. Sometimes in those with small amounts of bleeding no symptoms may be present.

<span class="mw-page-title-main">Gastric varices</span> Medical condition

Gastric varices are dilated submucosal veins in the lining of the stomach, which can be a life-threatening cause of bleeding in the upper gastrointestinal tract. 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. Gastric varices may also be found in patients with thrombosis of the splenic vein, into which the short gastric veins that drain the fundus of the stomach flow. The latter may be a complication of acute pancreatitis, pancreatic cancer, or other abdominal tumours, as well as hepatitis C. Gastric varices and associated bleeding are a potential complication of schistosomiasis resulting from portal hypertension.

<span class="mw-page-title-main">Embolization</span> Passage and lodging of an embolus within the bloodstream

Embolization refers to the passage and lodging of an embolus within the bloodstream. It may be of natural origin (pathological), in which sense it is also called embolism, for example a pulmonary embolism; or it may be artificially induced (therapeutic), as a hemostatic treatment for bleeding or as a treatment for some types of cancer by deliberately blocking blood vessels to starve the tumor cells.

<span class="mw-page-title-main">Ethyl cyanoacrylate</span> Chemical compound

Ethyl cyanoacrylate (ECA), a cyanoacrylate ester, is an ethyl ester of 2-cyano-acrylic acid. It is a colorless liquid with low viscosity and a faint sweet smell in pure form. It is the main component of cyanoacrylate glues and can be encountered under many trade names. It is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride. ECA polymerizes rapidly in presence of moisture.

<span class="mw-page-title-main">Distal splenorenal shunt procedure</span> Medical procedure

In medicine, a distal splenorenal shunt procedure (DSRS), also splenorenal shunt procedure and Warren shunt, is a surgical procedure in which the distal splenic vein is attached to the left renal vein. It is used to treat portal hypertension and its main complication. It was developed by W. Dean Warren.

<span class="mw-page-title-main">Sengstaken–Blakemore tube</span> Medical device

A Sengstaken–Blakemore tube is a medical device inserted through the nose or mouth and used occasionally in the management of upper gastrointestinal hemorrhage due to esophageal varices. The use of the tube was originally described in 1950, although similar approaches to bleeding varices were described by Westphal in 1930. With the advent of modern endoscopic techniques which can rapidly and definitively control variceal bleeding, Sengstaken–Blakemore tubes are rarely used at present.

<span class="mw-page-title-main">Endoclip</span>

An endoclip is a metallic mechanical device used in endoscopy in order to close two mucosal surfaces without the need for surgery and suturing. Its function is similar to a suture in gross surgical applications, as it is used to join together two disjointed surfaces, but, can be applied through the channel of an endoscope under direct visualization. Endoclips have found use in treating gastrointestinal bleeding, in preventing bleeding after therapeutic procedures such as polypectomy, and in closing gastrointestinal perforations. Many forms of endoclips exist of different shapes and sizes, including two and three prong devices, which can be administered using single use and reloadable systems, and may or may not open and close to facilitate placement.

<span class="mw-page-title-main">Portal hypertensive gastropathy</span> Changes in the mucosa of the stomach in patients with portal hypertension

Portal hypertensive gastropathy refers to changes in the mucosa of the stomach in patients with portal hypertension; by far the most common cause of this is cirrhosis of the liver. These changes in the mucosa include friability of the mucosa and the presence of ectatic blood vessels at the surface. Patients with portal hypertensive gastropathy may experience bleeding from the stomach, which may uncommonly manifest itself in vomiting blood or melena; however, portal hypertension may cause several other more common sources of upper gastrointestinal bleeding, such as esophageal varices and gastric varices. On endoscopic evaluation of the stomach, this condition shows a characteristic mosaic or "snake-skin" appearance to the mucosa of the stomach.

<span class="mw-page-title-main">Wound closure strip</span> Porous surgical tape used for closing small wounds

Wound closure strips are porous surgical tape strips which can be used to close small wounds. They are applied across the laceration in a manner which pulls the skin on either side of the wound together. Wound closure strips may be used instead of sutures (stitches) in some injuries, because they lessen scarring and are easier to care for.

<span class="mw-page-title-main">Octyl cyanoacrylate</span> Chemical compound

Octyl cyanoacrylate (OCA), 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.

Therapeutic endoscopy is the medical term for an endoscopic procedure during which treatment is carried out via the endoscope. This contrasts with diagnostic endoscopy, where the aim of the procedure is purely to visualize a part of the gastrointestinal, respiratory or urinary tract in order to aid diagnosis. In practice, a procedure which starts as a diagnostic endoscopy may become a therapeutic endoscopy depending on the findings, such as in cases of upper gastrointestinal bleeding, or the finding of polyps during colonoscopy.

<span class="mw-page-title-main">Isobutyl cyanoacrylate</span> Chemical compound

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 the presence of small amounts of moisture, rapidly polymerizes to form a strong adhesive.

<span class="mw-page-title-main">2-Octyl cyanoacrylate</span> Chemical compound

2-Octyl cyanoacrylate is a cyanoacrylate ester typically used as a wound closure adhesive. It is closely related to octyl cyanoacrylate. The use of 2-octyl cyanoacrylate was approved in 1998; offered as an alternative to stitches, sutures, and or adhesive strips.

<span class="mw-page-title-main">Nib Soehendra</span> German surgeon (born 1942)

Nib Soehendra is a German surgeon known for numerous contributions to the field of endoscopy and therapeutic endoscopy.

References

  1. 1 2 "Butyl cyanoacrylate". CAS Common Chemistry. American Chemical Society.
  2. 1 2 "n-Butyl-2-cyanoacrylate". Chemical Sampling Information. Washington, DC, USA: Occupational Safety & Health Administration. 17 January 2007. Retrieved 25 June 2011.
  3. ↑ "Material Safety Data Sheet for Butyl Octyl Blend" (PDF). GluStitch Inc. 19 October 2009. Archived from the original (PDF) on 26 March 2012. Retrieved 25 June 2011.
  4. ↑ "Cyanoacrylate Technical Data". Archived from the original on 2008-12-08. Retrieved 2008-12-17.
  5. ↑ Farion K, Osmond MH, Hartling L, et al. (2002). Farion KJ (ed.). "Tissue adhesives for traumatic lacerations in children and adults". Cochrane Database Syst Rev. 2010 (3): CD003326. doi:10.1002/14651858.CD003326. PMC   9006881 . PMID   12137689.
  6. ↑ Lee BB, Do YS, Yakes W, Kim DI, Mattassi R, Hyon WS (March 2004). "Management of arteriovenous malformations: a multidisciplinary approach". J. Vasc. Surg. 39 (3): 590–600. doi: 10.1016/j.jvs.2003.10.048 . PMID   14981454.
  7. ↑ Ferguson JW, Tripathi D, Hayes PC (August 2003). "Review article: the management of acute variceal bleeding". Aliment. Pharmacol. Ther. 18 (3): 253–62. doi:10.1046/j.1365-2036.2003.01664.x. PMID   12895210. S2CID   394376.
  8. ↑ D'Imperio N, Piemontese A, Baroncini D, et al. (February 1996). "Evaluation of undiluted N-butyl-2-cyanoacrylate in the endoscopic treatment of upper gastrointestinal tract varices". Endoscopy. 28 (2): 239–43. doi:10.1055/s-2007-1005435. PMID   8739740.
  9. ↑ Ota K, Shirai Z, Masuzaki T, et al. (August 1998). "Endoscopic injection sclerotherapy with n-butyl-2-cyanoacrylate for ruptured duodenal varices". J. Gastroenterol. 33 (4): 550–5. doi:10.1007/s005350050131. PMID   9719241. S2CID   24409897. Archived from the original on 2013-02-11.
  10. ↑ Chen WC, Hou MC, Lin HC, Chang FY, Lee SD (February 2000). "An endoscopic injection with N-butyl-2-cyanoacrylate used for colonic variceal bleeding: a case report and review of the literature". Am. J. Gastroenterol. 95 (2): 540–2. doi:10.1111/j.1572-0241.2000.01782.x. PMID   10685765. S2CID   20091551.
  11. ↑ Lo GH, Lai KH, Cheng JS, Chen MH, Chiang HT (May 2001). "A prospective, randomized trial of butyl cyanoacrylate injection versus band ligation in the management of bleeding gastric varices". Hepatology. 33 (5): 1060–4. doi: 10.1053/jhep.2001.24116 . PMID   11343232.
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