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Details

Stereochemistry ACHIRAL
Molecular Formula C17H28N2O3
Molecular Weight 308.4158
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENOXINATE

SMILES

CCCCOC1=CC(=CC=C1N)C(=O)OCCN(CC)CC

InChI

InChIKey=CMHHMUWAYWTMGS-UHFFFAOYSA-N
InChI=1S/C17H28N2O3/c1-4-7-11-21-16-13-14(8-9-15(16)18)17(20)22-12-10-19(5-2)6-3/h8-9,13H,4-7,10-12,18H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C17H28N2O3
Molecular Weight 308.4158
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Oxybuprocaine (benoxinate) hydrochloride (MINIMS®) is a local, surface anaesthetic of the ester type. It has been shown to give effective surface anaesthesia in short opthalmological procedures. Sensation of pain is locally and reversibly reduced, with the possibility of temperature and pressure sensitivity also affected. Anaesthetic activity is ten times that of cocaine and twice that of tetracaine (amethocaine). Oxybuprocaine (benoxinate) binds to sodium channel and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. Depolarization of the neuronal membrane is inhibited thereby blocking the initiation and conduction of nerve impulses.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MINIMS
PubMed

PubMed

TitleDatePubMed
Oxybuprocaine induces a false-positive response in immunochromatographic SAS Adeno Test.
2002 Apr
Randomized trial of superficial peribulbar compared with conventional peribulbar anesthesia for cataract extraction.
2007 Mar
Clinical investigation of the effect of topical anesthesia on intraocular pressure.
2007 Sep
Micropulse diode laser trabeculoplasty (MDLT): A phase II clinical study with 12 months follow-up.
2008 Jun
The challenge of dry eye diagnosis.
2008 Mar
Safety, efficacy, and patient acceptability of lidocaine hydrochloride ophthalmic gel as a topical ocular anesthetic for use in ophthalmic procedures.
2009
Correlation of flicker-induced and flow-mediated vasodilatation in patients with endothelial dysfunction and healthy volunteers.
2009 Aug
Evaluation of conjunctival inflammatory status by confocal scanning laser microscopy and conjunctival brush cytology in patients with atopic keratoconjunctivitis (AKC).
2009 Aug 15
Hypoxia-altered signaling pathways of toll-like receptor 4 (TLR4) in human corneal epithelial cells.
2009 Dec 2
[Peritopic anesthesia in cataract surgery].
2009 Feb
Management of Ocular Trauma in Emergency (MOTE) Trial: A pilot randomized double-blinded trial comparing topical amethocaine with saline in the outpatient management of corneal trauma.
2009 Jan
[Effect of double anaesthetic Colicursi (tetracaine 0.1% and oxybuprocaine 0.4%) on central and paracentral corneal thickness].
2009 Jan
Antibacterial activity of preservative-free topical anesthetic drops in current use in ophthalmology departments.
2009 Jan
In vivo observation of Langerhans cells by laser confocal microscopy in Thygeson's superficial punctate keratitis.
2009 Jul 29
Expression and potential role of major inflammatory cytokines in experimental keratomycosis.
2009 Jul 4
Topical anesthesia in strabismus surgery: a review of 101 cases.
2009 Jul-Aug
Guidelines for procedural pain in the newborn.
2009 Jun
Silencing of P2Y2 receptor delays Ap4A-corneal re-epithelialization process.
2009 Jun 11
Efficacy of sub-Tenon's block using an equal volume of local anaesthetic administered either as a single or as divided doses. A randomised clinical trial.
2009 Mar 26
Intrathecal oxybuprocaine and proxymetacaine produced potent and long-lasting spinal anesthesia in rats.
2009 May 1
Primary central nervous system lymphoma presenting as bilateral uveitis in an immunocompetent hepatitis C virus(+) patient: a case report.
2009 Oct 13
Retinal ischemia-induced apoptosis is associated with alteration in Bax and Bcl-x(L) expression rather than modifications in Bak and Bcl-2.
2009 Oct 19
Wide-field digital imaging based telemedicine for screening for acute retinopathy of prematurity (ROP). Six-year results of a multicentre field study.
2009 Sep
The systemic toxicity of equipotent proxymetacaine, oxybuprocaine, and bupivacaine during continuous intravenous infusion in rats.
2010 Jan 1
Patents

Sample Use Guides

In Vivo Use Guide
One drop of MINIMS® instilled into each eye has been shown sufficient for tonometry after one minute. Addition of a further drop after 90 seconds provides adequate anaesthesia for fitting of a contact lens. To obtain a deeper anaesthetic effect, further drops may be instilled at intervals of no less than 90 seconds. For most procedures one to two drops is sufficient, however for removal of foreign bodies or minor surgery, three to six drops is suggested.
Route of Administration: Topical ophthalmic
In Vitro Use Guide
The cytotoxic effect of oxybuprocaine (OBPC) on human corneal epithelial (HCEP) cells was characterized and its possible cellular and molecular mechanisms was investigated using an in vitro model of non-transfected HCEP cells. The results showed that OBPC at concentrations ranging from 0.025% to 0.4% had a dose- and time-dependent cytotoxicity to HCEP cells. Moreover, OBPC arrested the cells at S phase and induced apoptosis of these cells by inducing plasma membrane permeability, phosphatidylserine externalization, DNA fragmentation, and apoptotic body formation. Furthermore, OBPC could trigger the activation of caspase-2, -3, and -9, downregulate the expression of Bcl-xL, upregulate the expression of Bax along with the cytoplasmic amount of mitochondria-released apoptosis-inducing factor, and disrupt mitochondrial transmembrane potential.
Substance Class Chemical
Created
by admin
on Tue Mar 06 12:13:48 UTC 2018
Edited
by admin
on Tue Mar 06 12:13:48 UTC 2018
Record UNII
AXQ0JYM303
Record Status Validated (UNII)
Record Version
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Name Type Language
BENOXINATE
MI   VANDF  
Common Name English
BENZOIC ACID, 4-AMINO-3-BUTOXY-, 2-(DIETHYLAMINO)ETHYL ESTER
Common Name English
OXYBUPROCAINE
INN   WHO-DD  
INN  
Official Name English
4-AMINO-3-BUTOXYBENZOIC ACID 2-DIETHYLAMINOETHYL ESTER
Systematic Name English
BENOXINATE [VANDF]
Common Name English
OXYBUCAINE
Common Name English
2-(DIETHYLAMINO)ETHYL 4-AMINO-3-BUTOXYBENZOATE
Systematic Name English
OXYBUPROCAINE [WHO-DD]
Common Name English
DORSACAIN
Brand Name English
CONJUCAIN
Brand Name English
MONOFREE OXYBUPROCAINE
Brand Name English
BENOXINATE [MI]
Common Name English
OXYBUPROCAINE [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC D04AB03
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
WHO-VATC QD04AB03
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
WHO-VATC QS01HA02
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
WHO-ATC S01HA02
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
Code System Code Type Description
MESH
C005298
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
IUPHAR
7123
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
EPA CompTox
99-43-4
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
MERCK INDEX
M2319
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL1200
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
PUBCHEM
4633
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY SWITZERF
RXCUI
18889
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY RxNorm
EVMPD
SUB09557MIG
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
INN
275
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
DRUG BANK
DB00892
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
CAS
99-43-4
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
WIKIPEDIA
OXYBUPROCAINE
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
NCI_THESAURUS
C72176
Created by admin on Tue Mar 06 12:13:48 UTC 2018 , Edited by admin on Tue Mar 06 12:13:48 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY