n-Butyl cyanoacrylate (n-BCA, NBCA), a cyanoacrylateester, is a butylester 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.
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 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 applicationsEdit
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]
^ ab "n-Butyl-2-cyanoacrylate". Chemical Sampling Information. Washington, DC, USA: Occupational Safety & Health Administration. 17 January 2007. Retrieved 25 June 2011.
^(PDF). GluStitch Inc. 19 October 2009. Archived from the original (PDF) on 26 March 2012. Retrieved 25 June 2011.
^. Archived from the original on 2008-12-08. Retrieved 2008-12-17.
^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. PMC9006881. PMID 12137689.
^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.
^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.
^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.
^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.
^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.
^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.
October 15, 2023
butyl, cyanoacrylate, nbca, cyanoacrylate, ester, butyl, ester, cyano, propenoic, acid, colorless, liquid, with, sharp, irritating, odor, insoluble, water, chief, main, component, medical, cyanoacrylate, glues, encountered, under, various, trade, names, cutsea. 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 n Butyl cyanoacrylate NamesPreferred IUPAC name Butyl 2 cyanoprop 2 enoateOther names Butyl 2 cyanopropenoateButyl 2 cyanoacrylate2 Cyano 2 propenoic acid n butyl estern Butyl 2 cyanoacrylaten BCANBCAn Butyl alpha cyanoacrylateEnbucrilate INN IdentifiersCAS Number 6606 65 13D model JSmol Interactive imageChEMBL ChEMBL2104251ChemSpider 21607ECHA InfoCard 100 026 866EC Number 229 552 2PubChem CID 23087UNII F8CEP82QNP YCompTox Dashboard EPA DTXSID5064417InChI InChI 1 C8H11NO2 c1 3 4 5 11 8 10 7 2 6 9 h2 5H2 1H3Key JJJFUHOGVZWXNQ UHFFFAOYAKSMILES N CC C C O OCCCCPropertiesChemical formula C 8H 11N O 2Molar mass 153 181 g mol 1Density 0 986 g cm3 at 20 C 1 Boiling point 69 72 C 156 162 F 342 345 K 1 at 1 6 mmHgHazardsFlash point gt 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 Infobox references 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 EditThe 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 EditIsobutyl cyanoacrylate Methyl cyanoacrylate Ethyl cyanoacrylate Octyl cyanoacrylateReferences Edit a b https commonchemistry cas org detail cas rn 6606 65 1 a b n Butyl 2 cyanoacrylate Chemical Sampling Information Washington DC USA Occupational Safety amp Health Administration 17 January 2007 Retrieved 25 June 2011 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 Cyanoacrylate Technical Data Archived from the original on 2008 12 08 Retrieved 2008 12 17 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 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 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 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 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 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 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 Retrieved from https en wikipedia org w index php title Butyl cyanoacrylate amp oldid 1164539317, wikipedia, wiki, book, books, library,
