BUCRYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H11NO2
Molecular Weight	153.1784
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)COC(=O)C(=C)C#N

InChI

InChIKey=QRWOVIRDHQJFDB-UHFFFAOYSA-N

InChI=1S/C8H11NO2/c1-6(2)5-11-8(10)7(3)4-9/h6H,3,5H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C8H11NO2
Molecular Weight	153.1784
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30788517 | https://www.ncbi.nlm.nih.gov/pubmed/10917182 | https://www.ncbi.nlm.nih.gov/pubmed/3511383 | https://www.ncbi.nlm.nih.gov/pubmed/3512261

Bucrylate (isobutyl cyanoacrylate) is a liquid tissue adhesive for transcatheter embolization. It is used in radiological and endoscopic interventions to occlude vessels and to stop bleedings. In comparison with sponges, coils and plugs, bucrylate is inexpensive and achieves immediate, irreversible and complete occlusion of the vessel irrespective of coagulation deficiencies.

Originator

Approval Year

PubMed

Title	Date	PubMed
Secondary cytotoxicity mediated by alveolar macrophages: a contribution to the total efficacy of nanoparticles in lung cancer therapy?	2010-09	20452423
Spontaneous rupture of a giant hepatic hemangioma - sequential management with transcatheter arterial embolization and resection.	2010-03-27	20339183
Perfusion computed tomography in a dural arteriovenous fistula presenting with focal signs: vascular congestion as a cause of reversible neurologic dysfunction.	2010-01	20023531
Evaluation of therapeutic effects and serious complications following endoscopic obliterative therapy with Histoacryl.	2010	21694852
Editorial comment on: Reducing laparoscopic radical prostatectomy false-positive margin rates using cyanoacrylate tissue glue.	2009-10	19091456
Editorial comment on: Reducing laparoscopic radical prostatectomy false-positive margin rates using cyanoacrylate tissue glue.	2009-10	19091455
Reducing laparoscopic radical prostatectomy false-positive margin rates using cyanoacrylate tissue glue.	2009-10	19091454
[Case of repeated hemoptysis successfully treated with bronchial artery embolization with N-butyl cyanoacrylate].	2009-05	19514507
Percutaneous injection of hemostatic agents for severe blunt hepatic trauma: an experimental study.	2008-12	18618116
Percutaneous transportal sclerotherapy with N-butyl-2-cyanoacrylate for gastric varices: technique and clinical efficacy.	2008-11-29	19039269
Peripheral arteriovenous malformations with a dominant outflow vein: results of ethanol embolization.	2008-06-06	18525229
In vitro evaluation of calcium binding capacity of chitosan and thiolated chitosan poly(isobutyl cyanoacrylate) core-shell nanoparticles.	2007-06-29	17367968
Transcatheter arterial embolization of nonvariceal upper gastrointestinal bleeding with N-butyl cyanoacrylate.	2007-02-06	17277563
Tuning of shell and core characteristics of chitosan-decorated acrylic nanoparticles.	2007-02	17157487
Embolisation of proximal anastomotic pseudoaneurysm developing after surgical repair of abdominal aortic aneurysm with a bifurcated graft with n-butyl cyanoacrylate.	2006-12	17213297
Percutaneous protective coil occlusion of the proximal inferior mesenteric artery before N-butyl cyanoacrylate embolization of type II endoleaks after endovascular repair of abdominal aortic aneurysms.	2006-11	17142714
Busulfan loading into poly(alkyl cyanoacrylate) nanoparticles: physico-chemistry and molecular modeling.	2006-11	16924634
Embolization of an aortic arch pseudoaneurysm with coils and N-butyl-cyanoacrylate.	2006-10	17057010
Preparation and characterization of carbonyl iron/poly(butylcyanoacrylate) core/shell nanoparticles.	2006-07-15	16580009
Endovascular treatment of arterial injury as an uncommon complication after orthopedic surgery.	2006-05	16687744
Estimation of the remaining periodontal ligament from attachment-level measurements.	2006-03	16489949
Tissue reactions induced by different embolising agents in cerebral arteriovenous malformations: a histopathological follow-up.	2006-02	16484004
The effectiveness of isobutyl cyanoacrylate tissue adhesive for the treatment of corneal perforations.	2005-11	16310475
Determinants of staged endovascular and surgical treatment outcome of brain arteriovenous malformations.	2005-11	16224095
Controlled myocardial infarction induced by intracoronary injection of n-butyl cyanoacrylatein dogs: a feasibility study.	2005-10	16082687
The use of isobutylcyanoacrylate as a tissue adhesive in abdominal surgery.	2005-08	16184723
Embolization of type 2 endoleaks after endovascular repair of abdominal aortic aneurysms with use of cyanoacrylate with or without coils.	2005-06	15947050
A relevant in vitro rat model for the evaluation of blood-brain barrier translocation of nanoparticles.	2005-06	15905957
Physical and biological properties of a novel siloxane adhesive for soft tissue applications.	2005	15887653
Intra-arterial hepatic chemotherapy: management of liver tumors by percutaneous port-a-cath positioning.	2003-12	16767926
Novel polysaccharide-decorated poly(isobutyl cyanoacrylate) nanoparticles.	2003-11	14661923
Treatment of a primary type IA endoleak with a liquid embolic system under conditions of aortic occlusion.	2003-02	12563222
Scaffold-enhanced albumin and n-butyl-cyanoacrylate adhesives for tissue repair: ex vivo evaluation in a porcine model.	2003	12724912
Laser disintegration of cyanoacrylate clot with successful endoscopic removal of sclerotherapy needle from gastric varix.	2002-08	12173092
Cyanoacrylate tissue adhesive for treatment of refractory corneal ulceration.	2002-03	11940249
Endoscopic repair of bronchial dehiscence after lung transplantation.	2001-12	11789804
Use of Indermil tissue adhesive for closure of superficial skin lacerations in children.	2001-08	11460081
Use of isobutyl cyanoacrylate tissue adhesive to stabilize external eyelid weights in temporary treatment of facial palsies.	2001-05	11388381

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:50:40 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:40 GMT 2025`
Record UNII	2HJV1F859Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUCRYLATE

Official Name

English

BUCRILATE

Preferred Name

English

2-PROPENOIC ACID, 2-CYANO-, 2-METHYLPROPYL ESTER

Common Name

English

Bucrilate [WHO-DD]

Common Name

English

ISOBUTYL CYANOACRYLATE [MI]

Common Name

English

BUCRILATE [MART.]

Common Name

English

BUCRYLATE [USAN]

Common Name

English

ISOBUTYL CYANOACRYLATE

Systematic Name

English

Isobutyl 2-cyanoacrylate

Systematic Name

English

IBC

Code

English

bucrilate [INN]

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL2103950