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Details

Stereochemistry ACHIRAL
Molecular Formula C17H28N2O3
Molecular Weight 308.4158
Optical Activity NONE
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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.hmdb.ca/metabolites/HMDB15029

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.

Originator

Curator's Comment: Patent https://worldwide.espacenet.com/publicationDetails/biblio?CC=GB&NR=654484

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MINIMS

Approved Use

To produce local anaesthesia in the eye for short opthalmological procedures.

Launch Date

2000
Doses

Doses

DosePopulationAdverse events​
2 drop multiple, topical
Recommended
Dose: 2 drop
Route: topical
Route: multiple
Dose: 2 drop
Sources:
unhealthy
Other AEs: Corneal toxicity...
2 drop single, topical
Recommended
Dose: 2 drop
Route: topical
Route: single
Dose: 2 drop
Sources:
unhealthy
Other AEs: Injury corneal...
AEs

AEs

AESignificanceDosePopulation
Corneal toxicity
2 drop multiple, topical
Recommended
Dose: 2 drop
Route: topical
Route: multiple
Dose: 2 drop
Sources:
unhealthy
Injury corneal
2 drop single, topical
Recommended
Dose: 2 drop
Route: topical
Route: single
Dose: 2 drop
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The systemic toxicity of equipotent proxymetacaine, oxybuprocaine, and bupivacaine during continuous intravenous infusion in rats.
2010-01-01
Hypoxia-altered signaling pathways of toll-like receptor 4 (TLR4) in human corneal epithelial cells.
2009-12-02
Retinal ischemia-induced apoptosis is associated with alteration in Bax and Bcl-x(L) expression rather than modifications in Bak and Bcl-2.
2009-10-19
Primary central nervous system lymphoma presenting as bilateral uveitis in an immunocompetent hepatitis C virus(+) patient: a case report.
2009-10-13
Effect of topical corneal anaesthesia on ocular response analyzer parameters: pilot study.
2009-10
Wide-field digital imaging based telemedicine for screening for acute retinopathy of prematurity (ROP). Six-year results of a multicentre field study.
2009-09
Evaluation of conjunctival inflammatory status by confocal scanning laser microscopy and conjunctival brush cytology in patients with atopic keratoconjunctivitis (AKC).
2009-08-15
Correlation of flicker-induced and flow-mediated vasodilatation in patients with endothelial dysfunction and healthy volunteers.
2009-08
In vivo observation of Langerhans cells by laser confocal microscopy in Thygeson's superficial punctate keratitis.
2009-07-29
Expression and potential role of major inflammatory cytokines in experimental keratomycosis.
2009-07-04
Silencing of P2Y2 receptor delays Ap4A-corneal re-epithelialization process.
2009-06-11
Guidelines for procedural pain in the newborn.
2009-06
Intrathecal oxybuprocaine and proxymetacaine produced potent and long-lasting spinal anesthesia in rats.
2009-05-01
The effect of topical anesthesia on the rat electroretinogram.
2009-04
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.
2009-03-26
[Peritopic anesthesia in cataract surgery].
2009-02
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.
2009-01
[Effect of double anaesthetic Colicursi (tetracaine 0.1% and oxybuprocaine 0.4%) on central and paracentral corneal thickness].
2009-01
Antibacterial activity of preservative-free topical anesthetic drops in current use in ophthalmology departments.
2009-01
Safety, efficacy, and patient acceptability of lidocaine hydrochloride ophthalmic gel as a topical ocular anesthetic for use in ophthalmic procedures.
2009
Manual small incision cataract surgery under topical anesthesia with intracameral lignocaine: study on pain evaluation and surgical outcome.
2008-12-17
Effect of topical anesthetics on intraocular pressure and pachymetry.
2008-10-14
Truncation of retinoschisin protein associated with a novel splice site mutation in the RS1 gene.
2008-08-25
The application of in vivo laser confocal microscopy to the diagnosis and evaluation of meibomian gland dysfunction.
2008-07-09
Micropulse diode laser trabeculoplasty (MDLT): A phase II clinical study with 12 months follow-up.
2008-06
Nucleus and cell size changes in human bulbar conjunctival cells after soft contact lens wear, as assessed by impression cytology.
2008-06
Decellularizing corneal stroma using N2 gas.
2008-05-14
The effect of voluntary fasting and dehydration on flicker-induced retinal vascular dilation in a healthy individual: a case report.
2008-05-13
Specific detection of fungal pathogens by 18S rRNA gene PCR in microbial keratitis.
2008-04-29
Intravitreal triamcinolone acetonide inhibits breakdown of the blood-retinal barrier through differential regulation of VEGF-A and its receptors in early diabetic rat retinas.
2008-04
Intravitreal vs. subtenon triamcinolone acetonide for the treatment of diabetic cystoid macular edema.
2008-03-17
The challenge of dry eye diagnosis.
2008-03
Effects of intraoperative oxidated regenerated cellulose on wound healing reaction after glaucoma filtration surgery: a comparative study with Interceed and Surgicel.
2008-02-23
Recombinant anti-vascular endothelial growth factor fusion protein efficiently suppresses choridal neovasularization in monkeys.
2008-01-10
In vivo biopsy by laser confocal microscopy for evaluation of traumatic recurrent corneal erosion.
2008
Topical anesthesia in strabismus surgery: a review of 101 cases.
2007-11-25
Clinical investigation of the effect of topical anesthesia on intraocular pressure.
2007-09
Goldmann applanation tonometry over daily disposable contact lens: accuracy and safety of procedure.
2007-09
Impression cytology of a case of conjunctival metaplasia associated with oral carbamazepine use?
2007-09
Topical anesthesia-induced keratopathy after laser-assisted subepithelial keratectomy.
2007-08
Safety and efficacy of two ocular anesthetic methods for phacoemulsification: topical anesthesia and viscoanesthesia (VisThesia).
2007-04-07
Involvement of ER stress in retinal cell death.
2007-04-05
Linkage and association of myocilin (MYOC) polymorphisms with high myopia in a Chinese population.
2007-04-04
An assessment of regional differences in corneal thickness in normal human eyes, using the Orbscan II or ultrasound pachymetry.
2007-04
The Sandwell technique of Sub-Tenon's infiltration anesthesia for cataract surgery and other ophthalmic procedures.
2007-04
Randomized trial of superficial peribulbar compared with conventional peribulbar anesthesia for cataract extraction.
2007-03
On the use of Orbscan II to assess the peripheral corneal thickness in humans: a comparison with ultrasound pachometry measures.
2007-03
[Outpatient external dacryocystorhinostomy under regional anesthesia and sedation].
2007-01
Increased endothelin-1 levels of BAL fluid in patients with Behçet's disease.
2007
Positive and negative ion mass spectrometry and rapid isolation with Sep-Pak C18 cartridges of ten local anaesthetics.
1991-09
Patents

Sample Use Guides

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: Other
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 Mon Mar 31 18:11:25 GMT 2025
Edited
by admin
on Mon Mar 31 18:11:25 GMT 2025
Record UNII
AXQ0JYM303
Record Status Validated (UNII)
Record Version
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Name Type Language
BENOXINATE
MI   VANDF  
Common Name English
OXYBUPROCAINE
INN   WHO-DD  
INN  
Preferred Name English
BENZOIC ACID, 4-AMINO-3-BUTOXY-, 2-(DIETHYLAMINO)ETHYL ESTER
Common 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
DORSACAIN
Brand Name English
CONJUCAIN
Brand Name English
Oxybuprocaine [WHO-DD]
Common 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 Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
NCI_THESAURUS C245
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
WHO-VATC QD04AB03
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
WHO-VATC QS01HA02
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
WHO-ATC S01HA02
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
Code System Code Type Description
MESH
C005298
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
DRUG CENTRAL
3016
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
IUPHAR
7123
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
DAILYMED
AXQ0JYM303
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID7048530
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
CHEBI
309594
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
MERCK INDEX
m2319
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1200
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
SMS_ID
100000083300
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
PUBCHEM
4633
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
RXCUI
18889
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY RxNorm
EVMPD
SUB09557MIG
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
INN
275
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
DRUG BANK
DB00892
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
CAS
99-43-4
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
FDA UNII
AXQ0JYM303
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
WIKIPEDIA
OXYBUPROCAINE
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
NCI_THESAURUS
C72176
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
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