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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
4-Amino-3-butoxy-2-(diethylamino)ethyl ester benzoic acid
4-Amino-3-butoxy-benzoic acid 2-diethylamino-ethyl ester
4-Amino-3-N-butoxy-benzoesaeure-diaethylaminoaethylester
Benoxil
Benoxinate
BNX
Butoxyaminobenzoyldiethylaminoethanol
Oxibuprocaina
Oxybucaine
Oxybuprocainum
Oxyriprocaine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Minims Benoxinate Hydrochloride 0.4%drops.4 %ophthalmic; topicalChauvin Pharmaceuticals Limited1995-12-312003-07-08Canada
Unapproved/Other Products Not Available
International Brands
NameCompany
BenoxilSanten
CebesineChauvin Bausch & Lomb
ConjuncainNot Available
DorsacaineNot Available
LacriminSanten
NovesinNovartis
NovesineNovartis
PrescainaLlorens
Brand mixtures
NameLabellerIngredients
AltafluorAltaire Pharmaceuticals Inc.
Fluorescein Sodium & Benoxinate Hydrochloride Ophtalmic Solution, USPBausch & Lomb Inc
Fluorescein Sodium and Benoxinate HydrochlorideBausch & Lomb Incorporated
FluoroxWhite Ophthalmic Services & Supply Co Ltd
FluressAkorn, Inc.
Fluress Liq OphPilkington Barnes Hind
FluroxO Cu Soft, Inc.
Salts
Name/CASStructureProperties
Benoxinate hydrochloride
ThumbNot applicableDBSALT001482
Oxybuprocaine Hydrochloride
5987-82-6
Thumb
  • InChI Key: PRGUDWLMFLCODA-UHFFFAOYSA-N
  • Monoisotopic Mass: 344.186670511
  • Average Mass: 344.877
DBSALT000226
Categories
UNIIAXQ0JYM303
CAS number99-43-4
WeightAverage: 308.4158
Monoisotopic: 308.209992772
Chemical FormulaC17H28N2O3
InChI KeyInChIKey=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
IUPAC Name
2-(diethylamino)ethyl 4-amino-3-butoxybenzoate
SMILES
CCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Aminobenzoic acid or derivatives
  • Benzylether
  • Substituted aniline
  • Phenol ether
  • Benzoyl
  • Aniline
  • Alkyl aryl ether
  • Primary aromatic amine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9769
Blood Brain Barrier+0.8876
Caco-2 permeable+0.6501
P-glycoprotein substrateSubstrate0.7085
P-glycoprotein inhibitor INon-inhibitor0.7586
P-glycoprotein inhibitor IINon-inhibitor0.9645
Renal organic cation transporterNon-inhibitor0.7172
CYP450 2C9 substrateNon-substrate0.8202
CYP450 2D6 substrateNon-substrate0.5953
CYP450 3A4 substrateSubstrate0.5624
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9093
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5247
Ames testNon AMES toxic0.7542
CarcinogenicityNon-carcinogens0.7336
BiodegradationNot ready biodegradable0.9764
Rat acute toxicity2.5543 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8356
hERG inhibition (predictor II)Non-inhibitor0.5406
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sola barnes hind
Packagers
Dosage forms
FormRouteStrength
Solution/ dropsophthalmic
Liquidophthalmic
Solutionophthalmic
Dropsophthalmic; topical.4 %
Prices
Unit descriptionCostUnit
Fluress eye drops2.29USD ml
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 Solubility0.544 mg/mLALOGPS
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 Area64.79 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity90.64 m3·mol-1ChemAxon
Polarizability35.83 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.76 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot 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 ReferencesNot Available
External Links
ATC CodesD04AB03S01HA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (45.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity
Specific Function:
Tetrodotoxin-resistant channel that 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. Plays a role in neuropathic pain mechanisms.
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular Weight:
220623.605 Da
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:17139284 ]
  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:17016423 ]
  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. doi: 10.1016/j.neulet.2009.03.018. Epub 2009 Mar 11. [PubMed:19429093 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
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:4069587 ]
  2. Dubbels R, Schloot W: Studies on the metabolism of benoxinate by human pseudocholinesterase. Metab Pediatr Syst Ophthalmol. 1983;7(1):37-43. [PubMed:6621359 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on November 30, 2015 12:10