ENBUCRILATE

Possibly Marketed Outside US

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

CCCCOC(=O)C(=C)C#N

InChI

InChIKey=JJJFUHOGVZWXNQ-UHFFFAOYSA-N

InChI=1S/C8H11NO2/c1-3-4-5-11-8(10)7(2)6-9/h2-5H2,1H3

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.accessdata.fda.gov/cdrh_docs/pdf/P990040c.pdf | https://www.accessdata.fda.gov/cdrh_docs/pdf3/k031263.pdf

Enbucrilate (also known as n-butyl-cyanoacrylate, n-BCA) is an adhesive substance, which is used under different trade names (Histoacryl, 3M Liquid Bandage, etc) as an OTC medication for strong and secure wound closure. In 2000 FDA approved enbucrilate (TRUFILL n-BCA Liquid Embolic System) for presurgical embolization of cerebral arteriovenous malformations.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Arteriovenous malformations 2 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/P990040c.pdf	Primary		Approved 8429	TRUFILL Approved Use Presurgical embolization of cerebral arteriovenous malformations.
Wounds 15 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf3/k031263.pdf	Primary		Approved 8429	3M LIQUID BANDAGE Approved Use 3M Liquid Bandage is indicated for use as an over-the-counter (OTC) device for consumer use to cover minor cuts, scrapes, and skin irritations.

PubMed

Title	Date	PubMed
Facial wound closure with butyl 2-cyanoacrylate.	2003	15198307
Comparison of cyanoacrylate and silk sutures on healing of oral wounds--an animal model study.	2003 Oct-Dec	15328994
Ablation of symptomatic cysts using absolute ethanol in 11 patients with autosomal-dominant polycystic kidney disease.	2003 Oct-Dec	14726641
A pilot study of 2-octyl cyanoacrylate injection for treatment of gastric fundal varices in humans.	2004 Apr	15044898
Emergent transcatheter arterial embolization of ruptured inferior phrenic artery aneurysm with N-butyl cyanoacrylate.	2004 Aug	15297596
Endovascular treatment of a congenital dural caroticocavernous fistula.	2004 Aug	15024526
Contemporary diagnosis and management of venous and arterio-venous shunting malformation by whole body blood pool scintigraphy.	2004 Dec	15767981
The use of N-butyl cyanoacrylate (indermil) in lateral tarsorrhaphy.	2004 Feb	14769609
Hepatic myospherulosis complicating portal vein embolisation.	2004 Feb	14747440
N-butyl cyanoacrylate glue embolization of splenic artery aneurysms.	2004 Jan	14709694
N-butyl 2-cyanoacrylate injection via pancreatic collaterals to occlude splenic artery distal to large splenic aneurysm after proximal coil embolization.	2004 Jan	14684542
N-butyl cyanoacrylate embolization for control of acute arterial hemorrhage.	2004 Jul	15231881
Congested residual nidus after preoperative intranidal embolization in midsize cerebral arteriovenous malformations of 3-6 cm in diameter.	2004 Jul	15197607
Influence of polymerization technique and experimental variables on the particle properties and release kinetics of methotrexate from poly(butylcyanoacrylate) nanoparticles.	2004 Jun	15274754
Management of arteriovenous malformations: a multidisciplinary approach.	2004 Mar	14981454
Value of transcatheter arterial embolization with coils and n-butyl cyanoacrylate for long-term hepatic arterial infusion chemotherapy.	2004 Mar	14739309
Transhepatic embolization of a recanalized congenital hepatic arterioportal fistula with NBCA and coils.	2004 Mar-Apr	15259817
Complications of preoperative embolization of cerebral arteriovenous malformations.	2004 May	15137598
Transcatheter embolization of a coronary fistula originating from the left anterior descending artery by using n-butyl 2-cyanoacrylate.	2004 Nov-Dec	15593431
Direct percutaneous embolization of a carotid body tumor with n-butyl cyanoacrylate: an alternative method to endovascular embolization.	2004 Oct	15587423
Peripheral high-flow arteriovenous vascular malformations: a single-center experience.	2004 Oct	15466793
Use of the n-butyl cyanoacrylate adhesive and the polyglactine thread suture for corneal rhaphy in rabbit (Oryctolagus cunicullus).	2004 Sep	15365244
Clinical experience with butyl-2-cyanoacrylate adhesive in the management of canine and feline corneal disease.	2004 Sep-Oct	15310291
Physical and biological properties of a novel siloxane adhesive for soft tissue applications.	2005	15887653
Neonatal cavernous carotid artery aneurysm: case report.	2005 Apr	15881762
N-butyl 2-cyanoacrylate embolization of spinal dural arteriovenous fistulae: CT evaluation, technical features, and outcome prognosis in 26 cases.	2005 Apr	15814948
Acute and chronic swine rete arteriovenous malformation models: effect of ethiodol and glacial acetic acid on penetration, dispersion, and injection force of N-butyl 2-cyanoacrylate.	2005 Aug	16091519
Acute and chronic swine rete arteriovenous malformation models: hemodynamics and vascular remodeling.	2005 Aug	16091518
Portal vein embolization with N-butyl cyanoacrylate before partial hepatectomy in patients with hepatocellular carcinoma and underlying cirrhosis or advanced fibrosis.	2005 Dec	16371534
Plasticity of vagal afferents at the site of an incision in the wall of the stomach.	2005 Dec 30	16209938
Preoperative percutaneous portal vein embolization: evaluation of adverse events in 188 patients.	2005 Feb	15591428
Endovascular management of intracerebral and subarachnoid hemorrhage.	2005 Jul	16004851
Embolization of type 2 endoleaks after endovascular repair of abdominal aortic aneurysms with use of cyanoacrylate with or without coils.	2005 Jun	15947050
Management of difficult airway in intratracheal tumor surgery.	2005 Jun 7	15941480
Does treatment with N-butyl cyanoacrylate embolization protect against hemorrhage in cerebral arteriovenous malformations?	2005 Mar	15830062
Percutaneous sacroplasty for hemorrhagic metastases from hepatocellular carcinoma.	2005 Mar	15760854
Endovascular treatment of spinal arteriovenous fistula in a young child with hereditary hemorrhagic telangiectasia. Case report.	2005 Nov	16302622
Determinants of staged endovascular and surgical treatment outcome of brain arteriovenous malformations.	2005 Nov	16224095
Peripheral vascular malformations: imaging, treatment approaches, and therapeutic issues.	2005 Oct	16227489
Controlled myocardial infarction induced by intracoronary injection of n-butyl cyanoacrylatein dogs: a feasibility study.	2005 Oct	16082687
Cyanoacrylate for wound closure in prosthetic vascular graft surgery to prevent infections through contamination.	2006	16378194
Management of low-flow vascular malformations of upper aero digestive system-role of N-butyl cyanoacrylate in peroperative devascularization.	2006 Apr	15939512
Bleeding complications after endovascular therapy of cerebral arteriovenous malformations.	2006 Feb	16484399
Biliary duct ablation with N-butyl cyanoacrylate.	2006 Jan	16415134
Comparative dural closure techniques: a safety study in rats.	2006 Jan	16378853
Successful pregnancy with a full-term vaginal delivery one year after n-butyl cyanoacrylate embolization of a uterine arteriovenous malformation.	2006 Jul-Aug	16502173
A prospective, randomized controlled trial comparing n-butyl cyanoacrylate tissue adhesive (LiquiBand) with sutures for skin closure after laparoscopic general surgical procedures.	2006 Jun	16804456
Prenatal diagnosis of intracranial pial arteriovenous fistula and endovascular treatment during the neonatal period.	2006 Jun	16752350
Improved distal distribution of n-butyl cyanoacrylate glue by simultaneous injection of dextrose 5% through the guiding catheter: technical note.	2006 May	16607543
Spinal arteriovenous shunts presenting before 2 years of age: analysis of 13 cases.	2006 Sep	16586138

Sample Use Guides

In Vivo Use Guide

Topical: Apply the medication to the wound very sparingly, either as minute drops or as a very thin film along the edges of the wound. Infusion: A mixture of enbucrilate with Ethiodized Oil and tantalum powder (enbucrilate/Ethiodized oil ratio is 3:1, 2:1, 1:1, 1:2) is administered via a catheter.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:07:06 GMT 2023` Edited by `admin` on `Sat Dec 16 17:07:06 GMT 2023`
Record UNII	F8CEP82QNP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ENBUCRILATE

Official Name

English

GLUSTITCH

Brand Name

English

N-BUTYL CYANOACRYLATE

Common Name

English

ENBUCRILATE [MART.]

Common Name

English

MEDICRYL

Brand Name

English

VETBOND

Brand Name

English

N-BUTYL CYANOACRYLATE [MI]

Common Name

English

Enbucrilate [WHO-DD]

Common Name

English

PERIACRYL

Brand Name

English

MEDIBOND

Brand Name

English

N-BUTYL-2-CYANOACRYLATE

Common Name

English

BUTYL 2-CYANOACRYLATE

Systematic Name

English

enbucrilate [INN]

Common Name

English

Code System Code Type Description

FDA UNII

F8CEP82QNP