Cyanoacrylate Adhesives

Cyanoacrylate Adhesives Chemical formula

💊 Chemical information

Cianoacrilato, adhesivos de.
CAS — 1069-55-2 (bucrilate); 6606-65-1 (enbucrilate); 137-05-3 (mecrilate); 6701-17-3 (ocrilate);.

💊 Profile

A number of cyanoacrylate compounds have been used as surgical tissue adhesives. They include:
bucrilate (bucrylate; isobutyl 2-cyanoacrylate, C8H11NO2= 153.2)
enbucrilate (butyl 2-cyanoacrylate, C8H11NO2= 153.2),
mecrilate (mecrylate; methyl 2-cyanoacrylate, C5H5NO2= 111.1)
ocrilate (ocrylate; octil 2-cyanoacrylate, C12H19NO2= 209.3).
Some cyanoacrylates are used for household purposes and as nail fixatives and others have been investigated as tubal occlusive agents for female sterilisation, for sclerotherapy in bleeding gastric varices, and for embolisation of intracranial vascular lesions. Cyanoacrylate adhesives have also been used to plug corneal perforations until donor tissue is available.

Adverse effects.

Reports of inadvertent application of cyanoacrylate adhesives to the eyes,1,2 mouth,3 and ears.4,5 Pulmonary embolisation of ocrilate has been reported6 when it was used to obliterate gastric varices in a patient.
1. Lyons C, et al. Superglue inadvertently used as eyedrops. BMJ 1990; 300: 328
2. DeRespinis PA. Cyanoacrylate nail glue mistaken for eye drops. JAMA 1990; 263: 2301
3. Cousin GCS. Accidental application of cyanoacrylate to the mouth. Br Dent J 1990; 169: 293–4
4. O’Donnell JJ, et al. Cyanoacrylate adhesive mistaken for ear drops. J Accid Emerg Med 1997; 14: 199
5. Persaud R. A novel approach to the removal of superglue from the ear. J Laryngol Otol 2001; 115: 901–2
6. Rickman OB, et al. Pulmonary embolization of 2-octyl cyanoacrylate after endoscopic injection therapy for gastric variceal bleeding. Mayo Clin Proc 2004; 79: 1455–8.

Treatment of adverse effects.

In the event of accidental adhesion of the skin the bonded surfaces may be separated after application of acetone, prolonged soaking in warm (not hot) soapy water, and/or mixtures of alcohol and water. Application of liquid paraffin may help in removal from the skin. If necessary, the surfaces may be peeled or rolled apart with the aid of a spatula; attempts should not be made to pull the surfaces directly apart. Acetone and alcohol should not be used near or in the eyes. Solvents such as nitromethane, toluene, or xylene may be used to aid skin detachment from solid objects. Solvents should be used with care and should not be introduced into the oropharynx. Eyelids stuck together or bonded to the eyeball should be washed thoroughly with saline or water at room temperature for 15 minutes and a gauze patch applied; the eye will open without further action in 1 to 4 days. Manipulative attempts to open the eyes should not be made. Although cyanoacrylate introduced into the eyes may cause double vision and lachrymation there is usually no residual damage. If lips are accidentally stuck together plenty of warm water should be applied and maximum wetting from saliva inside the mouth encouraged. Lips should be peeled or rolled apart and not pulled. Adhesive introduced into the mouth solidifies and adheres, but saliva will lift the adhesive in ⁄ to 2 days. Care should be taken to avoid choking. Heat is evolved on solidification of cyanoacrylate and in rare cases may cause burns.


References to the use of cyanoacrylate adhesives,1-10 including bucrilate,1,2 enbucrilate,3,4 and ocrilate.5-9
1. Kind R, et al. Bucrylate treatment of bleeding gastric varices: 12 years’ experience. Endoscopy 2000; 32: 512–9
2. Shepler TR, Seiff SR. Use of isobutyl cyanoacrylate tissue adhesive to stabilize external eyelid weights in temporary treatment of facial palsies. Ophthal Plast Reconstr Surg 2001; 17: 169–73
3. Schonauer F, et al. Use of Indermil tissue adhesive for closure of superficial skin lacerations in children. Minerva Chir 2001; 56: 427–9
4. Sinha S, et al. A single blind, prospective, randomized trial comparing n-butyl 2-cyanoacrylate tissue adhesive (Indermil) and sutures for skin closure in hand surgery. J Hand Surg (Br) 2001; 26: 264–5
5. Kutcher MJ, et al. Evaluation of a bioadhesive device for the management of aphthous ulcers. J Am Dent Assoc 2001; 132: 368–76
6. Puri P. Tissue glue aided lid repositioning in temporary management of involutional entropion. Eur J Ophthalmol 2001; 11: 211–4
7. Bernard L, et al. A prospective comparison of octyl cyanoacrylate tissue adhesive (dermabond) and suture for the closure of excisional wounds in children and adolescents. Arch Dermatol 2001; 137: 1177–80
8. Mattick A, et al. A randomised, controlled trial comparing a tissue adhesive (2-octylcyanoacrylate) with adhesive strips (Steristrips) for paediatric laceration repair. Emerg Med J 2002; 19: 405–7
9. Magee WP, et al. Use of octyl-2-cyanoacrylate in cleft lip repair. Ann Plast Surg 2003; 50: 1–5
10. Singer AJ, et al. The cyanoacrylate topical skin adhesives. Am J Emerg Med 2008; 26: 490–6.

💊 Preparations

Proprietary Preparations

Arg.: Dermabond; Fr.: Dermabond; UK: Dermabond; Histoacryl; Indermil; LiquiBand; SuperSkin. Multi-ingredient: Ger.: Epiglu; Irl.: Epiglu; UK: Epiglu.
Published May 08, 2019.