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Identification
Name Oxybuprocaine
Accession Number DB00892 (APRD00817)
Type small molecule
Groups approved
Description

Oxybuprocaine is the name of a local anesthetic, which is used especially in ophthalmology and otolaryngology. Oxybuprocaine binds to sodium channels and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Benoxinate
Benoxinate HCL
Benoxinate hydrochloride
Dorsacaine hydrochloride
Oxbarukain
Oxibuprocainum
Oxibuprokain
Oxybucaine
Oxybuprocaine HCL
Oxybuprocaine hydrochloride
Oxyriprocaine
First Prev Next Last
Salts Not Available
Brand names
Name Company
Benoxil
Cebesine
Conjucain
Conjuncain
Dorsacain
Dorsacaine
Fluress
Lacrimin
Minims Benoxinate
Novesin
Novesina
Novesine
Novesinol
Opulets Benoxinate
Prescaina
First Prev Next Last
Brand mixtures
Brand Name Ingredients
Fluress Benoxinate Hydrochloride + Fluorescein Sodium
Categories
  • Anesthetics, Local
CAS number 99-43-4
Weight Average: 308.4158
Monoisotopic: 308.209992772
Chemical Formula C17H28N2O3
InChI Key InChIKey=CMHHMUWAYWTMGS-UHFFFAOYSA-N
InChI
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
Plain Text
IUPAC Name
2-(diethylamino)ethyl 4-amino-3-butoxybenzoate
SMILES
CCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC
Plain Text
Mass Spec show (8.76 KB)
Taxonomy
Kingdom Organic
Classes
  • Aminobenzoates
Substructures
  • Aminobenzoates
  • Carboxylic Acids and Derivatives
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Benzoates
  • Phenols and Derivatives
  • Aliphatic and Aryl Amines
  • Ethers
  • Benzene and Derivatives
  • Aromatic compounds
  • Anisoles
  • Benzoyl Derivatives
  • Phenyl Esters
  • Anilines
Pharmacology
Indication Used to temporarily numb the front surface of the eye so that the eye pressure can be measured or a foreign body removed.
Pharmacodynamics Oxybuprocaine is a local anaesthetic. It may be less irritating than tetracaine, and the onset and duration of action are similar to tetracaine.
Mechanism of action Oxybuprocaine 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00400 Oxybuprocaine Pathway SMP00400
Pharmacoeconomics
Manufacturers
  • Sola barnes hind
Packagers
Dosage forms
Form Route Strength
Solution Ophthalmic
Prices
Unit description Cost Unit
Fluress eye drops 2.29 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 216.5 °C at 2.00E+00 mm Hg Not Available
water solubility Very soluble (hydrochloride salt) Not Available
logP 3.1 Not Available
Predicted Properties
Property Value Source
water solubility 5.44e-01 g/l ALOGPS
logP 3.3 ALOGPS
logP 3.05 ChemAxon
logS -2.8 ALOGPS
pKa (strongest acidic) 19.76 ChemAxon
pKa (strongest basic) 8.96 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 64.79 ChemAxon
rotatable bond count 11 ChemAxon
refractivity 90.64 ChemAxon
polarizability 35.83 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01768 Link_out
PubChem Compound 4633 Link_out
PubChem Substance 46505399 Link_out
ChemSpider 4472 Link_out
BindingDB 50017709 Link_out
ChEBI 309594 Link_out
ChEMBL 309594 Link_out
Therapeutic Targets Database DAP001231 Link_out
PharmGKB PA164764617 Link_out
Drug Product Database 2148366 Link_out
RxList http://www.rxlist.com/cgi/generic2/fluress.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Oxybuprocaine Link_out
ATC Codes
  • D04AB03
  • S01HA02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (45.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Sodium channel protein type 10 subunit alpha

Pharmacological action: yes
Actions: inhibitor

This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms

Organism class: human
UniProt ID: Q9Y5Y9 Link_out
Gene: SCN10A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Hung CH, Wang JJ, Chen YC, Chu CC, Chen YW: Intrathecal oxybuprocaine and proxymetacaine produced potent and long-lasting spinal anesthesia in rats. Neurosci Lett. 2009 May 1;454(3):249-53. Epub 2009 Mar 11. Pubmed
Enzymes

1. Cholinesterase

Actions: substrate

An acylcholine + H(2)O = choline + a carboxylate

UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Draeger J, Schloot W, Wirt H: Interindividual differences of corneal sensitivity. Genetic aspects. Ophthalmic Paediatr Genet. 1985 Aug;6(1-2):291-5. Pubmed
  2. Dubbels R, Schloot W: Studies on the metabolism of benoxinate by human pseudocholinesterase. Metab Pediatr Syst Ophthalmol. 1983;7(1):37-43. Pubmed]
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19