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
Endoscopic repair of bronchial dehiscence after lung transplantation.	2001 Dec	11789804
Laser disintegration of cyanoacrylate clot with successful endoscopic removal of sclerotherapy needle from gastric varix.	2002 Aug	12173092
Intra-arterial hepatic chemotherapy: management of liver tumors by percutaneous port-a-cath positioning.	2003 Dec	16767926
Treatment of a primary type IA endoleak with a liquid embolic system under conditions of aortic occlusion.	2003 Feb	12563222
Novel polysaccharide-decorated poly(isobutyl cyanoacrylate) nanoparticles.	2003 Nov	14661923
Physical and biological properties of a novel siloxane adhesive for soft tissue applications.	2005	15887653
The use of isobutylcyanoacrylate as a tissue adhesive in abdominal surgery.	2005 Aug	16184723
Embolization of type 2 endoleaks after endovascular repair of abdominal aortic aneurysms with use of cyanoacrylate with or without coils.	2005 Jun	15947050
A relevant in vitro rat model for the evaluation of blood-brain barrier translocation of nanoparticles.	2005 Jun	15905957
Controlled myocardial infarction induced by intracoronary injection of n-butyl cyanoacrylatein dogs: a feasibility study.	2005 Oct	16082687
Embolisation of proximal anastomotic pseudoaneurysm developing after surgical repair of abdominal aortic aneurysm with a bifurcated graft with n-butyl cyanoacrylate.	2006 Dec	17213297
Tissue reactions induced by different embolising agents in cerebral arteriovenous malformations: a histopathological follow-up.	2006 Feb	16484004
Busulfan loading into poly(alkyl cyanoacrylate) nanoparticles: physico-chemistry and molecular modeling.	2006 Nov	16924634
Embolization of an aortic arch pseudoaneurysm with coils and N-butyl-cyanoacrylate.	2006 Oct	17057010
Tuning of shell and core characteristics of chitosan-decorated acrylic nanoparticles.	2007 Feb	17157487
Transcatheter arterial embolization of nonvariceal upper gastrointestinal bleeding with N-butyl cyanoacrylate.	2007 Jan-Feb	17277563
In vitro evaluation of calcium binding capacity of chitosan and thiolated chitosan poly(isobutyl cyanoacrylate) core-shell nanoparticles.	2007 Jun 29	17367968
Percutaneous injection of hemostatic agents for severe blunt hepatic trauma: an experimental study.	2008 Dec	18618116
Peripheral arteriovenous malformations with a dominant outflow vein: results of ethanol embolization.	2008 May-Jun	18525229
[Case of repeated hemoptysis successfully treated with bronchial artery embolization with N-butyl cyanoacrylate].	2009 May	19514507
Editorial comment on: Reducing laparoscopic radical prostatectomy false-positive margin rates using cyanoacrylate tissue glue.	2009 Oct	19091456
Editorial comment on: Reducing laparoscopic radical prostatectomy false-positive margin rates using cyanoacrylate tissue glue.	2009 Oct	19091455
Evaluation of therapeutic effects and serious complications following endoscopic obliterative therapy with Histoacryl.	2010	21694852
Spontaneous rupture of a giant hepatic hemangioma - sequential management with transcatheter arterial embolization and resection.	2010 Apr-Jun	20339183
Secondary cytotoxicity mediated by alveolar macrophages: a contribution to the total efficacy of nanoparticles in lung cancer therapy?	2010 Sep	20452423

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:13:17 GMT 2023`
Record UNII	2HJV1F859Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUCRYLATE

Official 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

Official Name

English

bucrilate [INN]

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL2103950