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Identification
NameOxybuprocaine
Accession NumberDB00892  (APRD00817)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
BenoxinateNot AvailableNot Available
BNXNot AvailableNot Available
Salts
Name/CAS Structure Properties
Oxybuprocaine Hydrochloride
5987-82-6
Thumb
  • InChI Key: PRGUDWLMFLCODA-UHFFFAOYSA-N
  • Monoisotopic Mass: 344.186670511
  • Average Mass: 344.877
DBSALT000226
Brand names
NameCompany
BenoxilSanten
CebesineChauvin Bausch & Lomb
ConjuncainNot Available
DorsacaineNot Available
LacriminSanten
NovesinNovartis
NovesineNovartis
PrescainaLlorens
Brand mixtures
Brand NameIngredients
FluressBenoxinate Hydrochloride + Fluorescein Sodium
Categories
CAS number99-43-4
WeightAverage: 308.4158
Monoisotopic: 308.209992772
Chemical FormulaC17H28N2O3
InChI KeyCMHHMUWAYWTMGS-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
IUPAC Name
2-(diethylamino)ethyl 4-amino-3-butoxybenzoate
SMILES
CCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC
Mass Specshow(8.76 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentBenzoic Acid Esters
Alternative parentsAminobenzoic Acid Derivatives; Benzylethers; Phenol Ethers; Benzoyl Derivatives; Alkyl Aryl Ethers; Anilines; Primary Aromatic Amines; Tertiary Amines; Carboxylic Acid Esters; Enolates; Polyamines; Dialkyl Ethers
Substituentsphenol ether; benzoyl; alkyl aryl ether; aniline; primary aromatic amine; carboxylic acid ester; tertiary amine; polyamine; ether; dialkyl ether; enolate; carboxylic acid derivative; primary amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzoic acid esters. These are ester derivatives of benzoic acid.
Pharmacology
IndicationUsed to temporarily numb the front surface of the eye so that the eye pressure can be measured or a foreign body removed.
PharmacodynamicsOxybuprocaine is a local anaesthetic. It may be less irritating than tetracaine, and the onset and duration of action are similar to tetracaine.
Mechanism of actionOxybuprocaine 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Oxybuprocaine Action PathwayDrug actionSMP00400
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9769
Blood Brain Barrier + 0.8876
Caco-2 permeable + 0.6501
P-glycoprotein substrate Substrate 0.7085
P-glycoprotein inhibitor I Non-inhibitor 0.7586
P-glycoprotein inhibitor II Non-inhibitor 0.9645
Renal organic cation transporter Non-inhibitor 0.7172
CYP450 2C9 substrate Non-substrate 0.8202
CYP450 2D6 substrate Non-substrate 0.5953
CYP450 3A4 substrate Substrate 0.5624
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.9093
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.831
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5247
Ames test Non AMES toxic 0.7542
Carcinogenicity Non-carcinogens 0.7336
Biodegradation Not ready biodegradable 0.9764
Rat acute toxicity 2.5543 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8356
hERG inhibition (predictor II) Non-inhibitor 0.5406
Pharmacoeconomics
Manufacturers
  • Sola barnes hind
Packagers
Dosage forms
FormRouteStrength
SolutionOphthalmic
Prices
Unit descriptionCostUnit
Fluress eye drops2.29USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point216.5 °C at 2.00E+00 mm HgNot Available
water solubilityVery soluble (hydrochloride salt)Not Available
logP3.1Not Available
Predicted Properties
PropertyValueSource
water solubility5.44e-01 g/lALOGPS
logP3.3ALOGPS
logP3.05ChemAxon
logS-2.8ALOGPS
pKa (strongest acidic)19.76ChemAxon
pKa (strongest basic)8.96ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count1ChemAxon
polar surface area64.79ChemAxon
rotatable bond count11ChemAxon
refractivity90.64ChemAxon
polarizability35.83ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Katsuyuki Inoo, Mitsuhiro Kawada, Kenjiro Mori, “Oxybuprocaine-Containing Analgesic/Antipruritic External Preparation.” U.S. Patent US20110124727, issued May 26, 2011.

US20110124727
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01768
PubChem Compound4633
PubChem Substance46505399
ChemSpider4472
BindingDB50017709
ChEBI309594
ChEMBL
Therapeutic Targets DatabaseDAP001231
PharmGKBPA164764617
Drug Product Database2148366
RxListhttp://www.rxlist.com/cgi/generic2/fluress.htm
WikipediaOxybuprocaine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(45.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Sodium channel protein type 10 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 10 subunit alpha Q9Y5Y9 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cholinesterase P06276 Details

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]

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12