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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 of ENBUCRILATE

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

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

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
TRUFILL

Approved Use

Presurgical embolization of cerebral arteriovenous malformations.
Primary
Approved
8583
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.
Doses

Doses

DosePopulationAdverse events​
single, topical
Route: topical
Route: single
Sources:
https://pubmed.ncbi.nlm.nih.gov/12384264/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/12384264/
Sources:
https://pubmed.ncbi.nlm.nih.gov/12384264/
66 % single, topical
Highest studied dose
Dose: 66 %
Route: topical
Route: single
Dose: 66 %
Sources:
https://pubmed.ncbi.nlm.nih.gov/24976100/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/24976100/
Sources:
https://pubmed.ncbi.nlm.nih.gov/24976100/
PubMed

PubMed

TitleDatePubMed
Spinal arteriovenous shunts presenting before 2 years of age: analysis of 13 cases.
2006-09
A prospective, randomized controlled trial comparing n-butyl cyanoacrylate tissue adhesive (LiquiBand) with sutures for skin closure after laparoscopic general surgical procedures.
2006-06
Prenatal diagnosis of intracranial pial arteriovenous fistula and endovascular treatment during the neonatal period.
2006-06
Improved distal distribution of n-butyl cyanoacrylate glue by simultaneous injection of dextrose 5% through the guiding catheter: technical note.
2006-05
Management of low-flow vascular malformations of upper aero digestive system-role of N-butyl cyanoacrylate in peroperative devascularization.
2006-04
Successful pregnancy with a full-term vaginal delivery one year after n-butyl cyanoacrylate embolization of a uterine arteriovenous malformation.
2006-02-28
Bleeding complications after endovascular therapy of cerebral arteriovenous malformations.
2006-02
Biliary duct ablation with N-butyl cyanoacrylate.
2006-01
Comparative dural closure techniques: a safety study in rats.
2006-01
Cyanoacrylate for wound closure in prosthetic vascular graft surgery to prevent infections through contamination.
2006
Plasticity of vagal afferents at the site of an incision in the wall of the stomach.
2005-12-30
Portal vein embolization with N-butyl cyanoacrylate before partial hepatectomy in patients with hepatocellular carcinoma and underlying cirrhosis or advanced fibrosis.
2005-12
Endovascular treatment of spinal arteriovenous fistula in a young child with hereditary hemorrhagic telangiectasia. Case report.
2005-11
Determinants of staged endovascular and surgical treatment outcome of brain arteriovenous malformations.
2005-11
Peripheral vascular malformations: imaging, treatment approaches, and therapeutic issues.
2005-10
Controlled myocardial infarction induced by intracoronary injection of n-butyl cyanoacrylatein dogs: a feasibility study.
2005-10
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.
2005-08
Acute and chronic swine rete arteriovenous malformation models: hemodynamics and vascular remodeling.
2005-08
Endovascular management of intracerebral and subarachnoid hemorrhage.
2005-07
Management of difficult airway in intratracheal tumor surgery.
2005-06-07
Embolization of type 2 endoleaks after endovascular repair of abdominal aortic aneurysms with use of cyanoacrylate with or without coils.
2005-06
Neonatal cavernous carotid artery aneurysm: case report.
2005-04
N-butyl 2-cyanoacrylate embolization of spinal dural arteriovenous fistulae: CT evaluation, technical features, and outcome prognosis in 26 cases.
2005-04
Does treatment with N-butyl cyanoacrylate embolization protect against hemorrhage in cerebral arteriovenous malformations?
2005-03
Percutaneous sacroplasty for hemorrhagic metastases from hepatocellular carcinoma.
2005-03
Preoperative percutaneous portal vein embolization: evaluation of adverse events in 188 patients.
2005-02
Physical and biological properties of a novel siloxane adhesive for soft tissue applications.
2005
Transcatheter embolization of a coronary fistula originating from the left anterior descending artery by using n-butyl 2-cyanoacrylate.
2004-12-14
Contemporary diagnosis and management of venous and arterio-venous shunting malformation by whole body blood pool scintigraphy.
2004-12
Direct percutaneous embolization of a carotid body tumor with n-butyl cyanoacrylate: an alternative method to endovascular embolization.
2004-10
Peripheral high-flow arteriovenous vascular malformations: a single-center experience.
2004-10
Use of the n-butyl cyanoacrylate adhesive and the polyglactine thread suture for corneal rhaphy in rabbit (Oryctolagus cunicullus).
2004-09
Comparison of cyanoacrylate and silk sutures on healing of oral wounds--an animal model study.
2004-08-27
Clinical experience with butyl-2-cyanoacrylate adhesive in the management of canine and feline corneal disease.
2004-08-18
Emergent transcatheter arterial embolization of ruptured inferior phrenic artery aneurysm with N-butyl cyanoacrylate.
2004-08
Endovascular treatment of a congenital dural caroticocavernous fistula.
2004-08
Transhepatic embolization of a recanalized congenital hepatic arterioportal fistula with NBCA and coils.
2004-07-21
N-butyl cyanoacrylate embolization for control of acute arterial hemorrhage.
2004-07
Congested residual nidus after preoperative intranidal embolization in midsize cerebral arteriovenous malformations of 3-6 cm in diameter.
2004-07
Influence of polymerization technique and experimental variables on the particle properties and release kinetics of methotrexate from poly(butylcyanoacrylate) nanoparticles.
2004-06
Complications of preoperative embolization of cerebral arteriovenous malformations.
2004-05
A pilot study of 2-octyl cyanoacrylate injection for treatment of gastric fundal varices in humans.
2004-04
Management of arteriovenous malformations: a multidisciplinary approach.
2004-03
Value of transcatheter arterial embolization with coils and n-butyl cyanoacrylate for long-term hepatic arterial infusion chemotherapy.
2004-03
The use of N-butyl cyanoacrylate (indermil) in lateral tarsorrhaphy.
2004-02
Hepatic myospherulosis complicating portal vein embolisation.
2004-02
Ablation of symptomatic cysts using absolute ethanol in 11 patients with autosomal-dominant polycystic kidney disease.
2004-01-17
N-butyl cyanoacrylate glue embolization of splenic artery aneurysms.
2004-01
N-butyl 2-cyanoacrylate injection via pancreatic collaterals to occlude splenic artery distal to large splenic aneurysm after proximal coil embolization.
2004-01
Facial wound closure with butyl 2-cyanoacrylate.
2003

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 Wed Apr 02 08:45:24 GMT 2025
Edited
by admin
on Wed Apr 02 08:45:24 GMT 2025
Record UNII
F8CEP82QNP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N-BUTYL CYANOACRYLATE
MI  
Preferred Name English
ENBUCRILATE
INN   MART.   WHO-DD  
INN  
Official Name English
GLUSTITCH
Brand 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
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
MESH
D004659
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
CHEBI
53497
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
ECHA (EC/EINECS)
229-552-2
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
INN
3796
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
ChEMBL
CHEMBL2104251
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
EVMPD
SUB06518MIG
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
SMS_ID
100000080204
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
NCI_THESAURUS
C169945
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
DRUG BANK
DB12358
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
DRUG CENTRAL
3056
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
PUBCHEM
23087
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
WIKIPEDIA
BUTYL CYANOACRYLATE
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
CAS
6606-65-1
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID5064417
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY
MERCK INDEX
m2836
Created by admin on Wed Apr 02 08:45:24 GMT 2025 , Edited by admin on Wed Apr 02 08:45:24 GMT 2025
PRIMARY Merck Index
Related Record Type Details
Structure of ENBUCRILATE
ACTIVE MOIETY
NIH
NCATS
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