BENOXINATE

First approved in 1953

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 Search

SMILES

CCCCOC1=C(N)C=CC(=C1)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
Sources: https://gp2u.com.au/static/pdf/O/OXYBUPROCAINE_MINIMS-PI.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: https://gp2u.com.au/static/pdf/O/OXYBUPROCAINE_MINIMS-PI.pdf	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://gp2u.com.au/static/pdf/O/OXYBUPROCAINE_MINIMS-PI.pdf	Primary		Approved 8429	MINIMS Approved Use To produce local anaesthesia in the eye for short opthalmological procedures. Launch Date 2000

Doses

Dose	Population	Adverse events
2 drop multiple, topical (max) Recommended Dose: 2 drop Route: topical Route: multiple Dose: 2 drop Co-administed with:: fluorescein sodium(Recommended) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: pain Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1	Other AEs: Corneal toxicity... Other AEs: Corneal toxicity Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1
2 drop single, topical (max) Recommended Dose: 2 drop Route: topical Route: single Dose: 2 drop Co-administed with:: fluorescein sodium(Recommended) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: pain Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1	Other AEs: Injury corneal... Other AEs: Injury corneal Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
Corneal toxicity		2 drop multiple, topical (max) Recommended Dose: 2 drop Route: topical Route: multiple Dose: 2 drop Co-administed with:: fluorescein sodium(Recommended) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: pain Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1
Injury corneal		2 drop single, topical (max) Recommended Dose: 2 drop Route: topical Route: single Dose: 2 drop Co-administed with:: fluorescein sodium(Recommended) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: pain Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208582Orig1s000lbl.pdf Page: p.1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.7 36

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.7 36	inhibitor 3277 Sources: https://www.cell.com/biophysj/comments/S0006-3495(16)33592-5	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY583584	https://www.001chemical.com/chem/99-43-4
Achemtek	0104-013343	http://www.achemtek.com/5987-82-6
Achemtek	0104-015817	http://www.achemtek.com/99-43-4
Alinda	ALBB-025704	http://alinda.ru/finechem_en_.html?i=ALBB-025704
Ambeed	A860351	https://www.ambeed.com/products/99-43-4.html
Aurum Pharmatech LLC	R1237	http://www.Aurumpharmatech.com/Product/ProductDetails/R1237
AvaChem Scientific	4675B	http://www.avachem.com/productSearch.asp?4675B
BLD Pharm	BD341809	http://www.bldpharm.com/products/99-43-4.html
ChemMol	99185726	http://www.chemmol.com/chemmol/99185726.html
Chemspace	CSSB00020600810	https://chem-space.com/CSSB00020600810
Finetech	FT-0659855	http://www.finetechnology-ind.com/prod/detail/pub/99-43-4.html
Lab Network	LN00263613	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00263613
Matrix Scientific	202177	https://www.matrixscientific.com/202177.html
MolPort	MolPort-006-167-653	https://www.molport.com/shop/molecule-link/MolPort-006-167-653
Molcore	MC583584	https://www.molcore.com/product/99-43-4
OChem	11518	http://www.ocheminc.com/index.php?act=psearch&pid=099A434
Oakwood	375116	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=146590&ExtHyperLink=1
Smolecule	S538412	http://www.smolecule.com/products/s538412
Smolecule	S793317	https://www.smolecule.com/products/s793317
THE BioTek	bt-278066	https://www.thebiotek.com/product/inhibitors/bt-278066
abcr GmbH	AB564485	http://www.abcr.com/shop/en/AB564485
eNovation Chemicals	D675230	https://www.enovationchem.com/ProductDetails.asp?ProductID=D675230
iChemical	EBD44526	http://www.ichemical.com/chemicals/cas-99-43-4
mcule	MCULE-5566120451	https://mcule.com/MCULE-5566120451/

PubMed

Title	Date	PubMed
Oxybuprocaine induces a false-positive response in immunochromatographic SAS Adeno Test.	2002 Apr	11927446
[Relevant allergans by periorbital allergic contact dermatitis. Oxybuprocain, an underestimated allergen].	2003 Aug	12955444
Corneal thickness values before and after oxybuprocaine 0.4% eye drops.	2003 Aug	12883345
Refractive outcomes after arcuate keratotomy using the Terry astigmatome.	2003 Dec	14709303
Oxybuprocaine induces a false positive.	2004 Aug	15288997
A little trick to reduce pain at the moment of blepharoplasty stitch removal.	2006 Apr	16582827
Linkage and association of myocilin (MYOC) polymorphisms with high myopia in a Chinese population.	2007 Apr 4	17438518
Involvement of ER stress in retinal cell death.	2007 Apr 5	17438523
NMR crystallography of oxybuprocaine hydrochloride, Modification II degrees.	2007 Jan 21	17199152
On the use of Orbscan II to assess the peripheral corneal thickness in humans: a comparison with ultrasound pachometry measures.	2007 Mar	17324208
Clinical investigation of the effect of topical anesthesia on intraocular pressure.	2007 Sep	19668485
In vivo biopsy by laser confocal microscopy for evaluation of traumatic recurrent corneal erosion.	2008	19093010
Decellularizing corneal stroma using N2 gas.	2008 May 14	18490960
Safety, efficacy, and patient acceptability of lidocaine hydrochloride ophthalmic gel as a topical ocular anesthetic for use in ophthalmic procedures.	2009	19898665
The effect of topical anesthesia on the rat electroretinogram.	2009 Apr	18665412
Hypoxia-altered signaling pathways of toll-like receptor 4 (TLR4) in human corneal epithelial cells.	2009 Dec 2	19960069
[Peritopic anesthesia in cataract surgery].	2009 Feb	19253175
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	19561949
[Effect of double anaesthetic Colicursi (tetracaine 0.1% and oxybuprocaine 0.4%) on central and paracentral corneal thickness].	2009 Jan	19173135
Manual small incision cataract surgery under topical anesthesia with intracameral lignocaine: study on pain evaluation and surgical outcome.	2009 Jan-Feb	19075400
Topical anesthesia in strabismus surgery: a review of 101 cases.	2009 Jul-Aug	19645400
Guidelines for procedural pain in the newborn.	2009 Jun	19484828
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	19323806
Primary central nervous system lymphoma presenting as bilateral uveitis in an immunocompetent hepatitis C virus(+) patient: a case report.	2009 Oct 13	19946523

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: Other

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 `Fri Dec 15 15:52:03 GMT 2023` Edited by `admin` on `Fri Dec 15 15:52:03 GMT 2023`
Record UNII	AXQ0JYM303
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENOXINATE

Common Name

English

BENZOIC ACID, 4-AMINO-3-BUTOXY-, 2-(DIETHYLAMINO)ETHYL ESTER

Common Name

English

OXYBUPROCAINE

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

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