Oxybuprocaine

Identification

Summary

Oxybuprocaine is a local anesthetic used in ophthalmology.

Brand Names
Altafluor, Fluress
Generic Name
Oxybuprocaine
DrugBank Accession Number
DB00892
Background

Oxybuprocaine (also known as Benoxinate) is 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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 308.4158
Monoisotopic: 308.209992772
Chemical Formula
C17H28N2O3
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-benzoesäure-diäthylaminoäthylester
  • Benoxinate
  • BNX
  • Butoxyaminobenzoyldiethylaminoethanol
  • Oxibuprocaina
  • Oxybucaine
  • Oxybuprocaine
  • Oxybuprocainum
  • Oxyriprocaine

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.

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Associated Therapies
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ASodium channel protein type 10 subunit alpha
inhibitor
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Oxybuprocaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Oxybuprocaine is combined with 1,2-Benzodiazepine.
AbemaciclibThe risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Oxybuprocaine.
AbirateroneThe risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Oxybuprocaine.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Oxybuprocaine.
AcetazolamideThe risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Oxybuprocaine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxybuprocaine hydrochloride0VE4U49K155987-82-6PRGUDWLMFLCODA-UHFFFAOYSA-N
International/Other Brands
Benoxil (Santen) / Cebesine (Chauvin Bausch & Lomb) / Conjuncain / Dorsacaine / Lacrimin (Santen) / Novesin (Novartis) / Novesine (Novartis) / Prescaina (Llorens)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Minims Benoxinate Hydrochloride 0.4%Solution / drops.4 %Ophthalmic; TopicalChauvin Pharmaceuticals Limited1995-12-312003-07-08Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AltafluorOxybuprocaine hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)SolutionOphthalmicAltaire Pharmaceuticals Inc.2018-03-01Not applicableUS flag
AltafluorOxybuprocaine hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)SolutionOphthalmicAltaire Pharmaceuticals Inc.2017-01-012018-04-19US flag
AMIGDAL-B®Oxybuprocaine hydrochloride (0.2 mg) + Cetylpyridinium chloride (1 mg)TabletBuccal; OralCOLOMPACK S.A2009-06-12Not applicableColombia flag
DIMETAPP GARGANTA® TABLETAS MASTICABLESOxybuprocaine hydrochloride (0.2 mg) + Cetylpyridinium chloride (1 mg)Tablet, chewableBuccalCOLOMPACK S.A.2018-04-232019-08-16Colombia flag
Fluorescein Sodium & Benoxinate Hydrochloride Ophthalmic Solution, USPOxybuprocaine hydrochloride (0.4 %) + Fluorescein sodium (0.25 %)SolutionOphthalmicBausch & Lomb Inc1998-10-27Not applicableCanada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Fluorescein Sodium and Benoxinate HydrochlorideOxybuprocaine hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)Solution / dropsOphthalmicBausch & Lomb Incorporated1995-01-012017-06-01US flag
FluressOxybuprocaine hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)Solution / dropsOphthalmicAkorn, Inc.1995-02-01Not applicableUS flag
FluroxOxybuprocaine hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)SolutionOphthalmicOCuSOFT, INC.2014-01-29Not applicableUS flag
FluroxOxybuprocaine hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)SolutionOphthalmicO Cu Soft, Inc.2006-08-302012-02-29US flag

Categories

ATC Codes
S01HA02 — OxybuprocaineD04AB03 — Oxybuprocaine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acid esters
Alternative Parents
Aminobenzoic acids and derivatives / Aminophenyl ethers / Phenoxy compounds / Benzoyl derivatives / Aniline and substituted anilines / Alkyl aryl ethers / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives
show 4 more
Substituents
Alkyl aryl ether / Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aminophenyl ether / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carboxylic acid derivative
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amino compound, substituted aniline, benzoate ester, amino acid ester (CHEBI:309594)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
AXQ0JYM303
CAS number
99-43-4
InChI Key
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=CC(=CC=C1N)C(=O)OCCN(CC)CC

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 References
Not Available
Human Metabolome Database
HMDB0015029
KEGG Drug
D08319
PubChem Compound
4633
PubChem Substance
46505399
ChemSpider
4472
BindingDB
50225499
RxNav
18889
ChEBI
309594
ChEMBL
CHEMBL1200
ZINC
ZINC000002019492
Therapeutic Targets Database
DAP001231
PharmGKB
PA164764617
RxList
RxList Drug Page
Wikipedia
Oxybuprocaine
MSDS
Download (45.5 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Sola barnes hind
Packagers
  • Akorn Inc.
Dosage Forms
FormRouteStrength
TabletBuccal; Oral
TabletOral
SolutionTopical1 %
Solution / dropsOphthalmic0.4 %
Tablet, chewableBuccal
Solution / dropsOphthalmic
LiquidOphthalmic
SolutionOphthalmic
Solution / dropsOphthalmic; Topical.4 %
Solution / dropsOphthalmic4 mg/ml
Solution / dropsOphthalmic
SolutionConjunctival; Ophthalmic4 mg
SolutionOphthalmic4 mg
Prices
Unit descriptionCostUnit
Fluress eye drops2.29USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US10293047No2019-05-212037-11-15US flag
US10632197No2020-04-282037-11-15US flag
US10842872No2020-11-242037-11-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)216.5 °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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Download (8.76 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-9320000000-9e6c5bbd587418179c4b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000l-2910000000-8a2be292eaed70f08bb5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-1859000000-3b240274fd7f0f80ebf2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1947000000-a4abb4f3534aa12861d0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zgi-1931000000-ff430bf4c1a30c5e85a1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1900000000-f8f848507105a9c8ab60
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-2900000000-a7f6296e8de30d967fe4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udr-0910000000-1b63f30b00303e7622d0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-184.9057535
predicted
DarkChem Lite v0.1.0
[M-H]-175.35005
predicted
DeepCCS 1.0 (2019)
[M+H]+185.0268535
predicted
DarkChem Lite v0.1.0
[M+H]+177.70805
predicted
DeepCCS 1.0 (2019)
[M+Na]+184.8708535
predicted
DarkChem Lite v0.1.0
[M+Na]+183.80121
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
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 acro...
Gene Name
SCN10A
Uniprot ID
Q9Y5Y9
Uniprot Name
Sodium channel protein type 10 subunit alpha
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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
Uniprot Name
Cholinesterase
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. [Article]
  2. Dubbels R, Schloot W: Studies on the metabolism of benoxinate by human pseudocholinesterase. Metab Pediatr Syst Ophthalmol. 1983;7(1):37-43. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48