Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H28N2O3.ClH |
| Molecular Weight | 344.877 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCCOC1=CC(=CC=C1N)C(=O)OCCN(CC)CC
InChI
InChIKey=PRGUDWLMFLCODA-UHFFFAOYSA-N
InChI=1S/C17H28N2O3.ClH/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;1H
DescriptionCurator's Comment: description was created based on several sources, including
http://www.hmdb.ca/metabolites/HMDB15029
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.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13147619
Curator's Comment: Patent https://worldwide.espacenet.com/publicationDetails/biblio?CC=GB&NR=654484
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
2 drop multiple, topical Recommended Dose: 2 drop Route: topical Route: multiple Dose: 2 drop Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Corneal toxicity... Other AEs: Corneal toxicity Sources: |
2 drop single, topical Recommended Dose: 2 drop Route: topical Route: single Dose: 2 drop Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Injury corneal... Other AEs: Injury corneal Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Corneal toxicity | 2 drop multiple, topical Recommended Dose: 2 drop Route: topical Route: multiple Dose: 2 drop Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Injury corneal | 2 drop single, topical Recommended Dose: 2 drop Route: topical Route: single Dose: 2 drop Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27590991
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.
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NCI_THESAURUS |
C245
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235398
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C005298
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C65251
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m2319
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DTXSID4045393
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759847
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ACTIVE MOIETY
SUBSTANCE RECORD