Identification

Name
Oxybuprocaine
Accession Number
DB00892  (APRD00817)
Type
Small Molecule
Groups
Approved, Investigational
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-benzoesäure-diäthylaminoäthylester
  • Benoxil
  • Benoxinate
  • BNX
  • Butoxyaminobenzoyldiethylaminoethanol
  • Oxibuprocaina
  • Oxybucaine
  • Oxybuprocainum
  • Oxyriprocaine
Product Ingredients
IngredientUNIICASInChI Key
Benoxinate hydrochlorideNot AvailableNot AvailableNot applicable
Oxybuprocaine Hydrochloride0VE4U49K155987-82-6PRGUDWLMFLCODA-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Minims Benoxinate Hydrochloride 0.4%Solution / drops.4 %Ophthalmic; TopicalChauvin Pharmaceuticals Limited1995-12-312003-07-08Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AltafluorOxybuprocaine Hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)SolutionOphthalmicAltaire Pharmaceuticals Inc.2018-03-01Not applicableUs
Fluorescein Sodium & Benoxinate Hydrochloride Ophthalmic Solution, USPBenoxinate hydrochloride (0.4 %) + Fluorescein sodium (0.25 %)SolutionOphthalmicBausch & Lomb Inc1998-10-27Not applicableCanada
FluoroxBenoxinate hydrochloride (0.4 %) + Fluorescein sodium (0.25 %)SolutionOphthalmicWhite Ophthalmic Services & Supply Co Ltd2011-11-282013-08-19Canada
FluressBenoxinate hydrochloride (0.4 %) + Fluorescein sodium (0.25 %)SolutionOphthalmicAkorn Inc1996-12-18Not applicableCanada
Fluress Liq OphBenoxinate hydrochloride (0.4 %) + Fluorescein sodium (0.25 %)LiquidOphthalmicPilkington Barnes Hind1969-12-311997-08-14Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AltafluorOxybuprocaine Hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)SolutionOphthalmicAltaire Pharmaceuticals Inc.2000-06-21Not applicableUs
Fluorescein Sodium and Benoxinate HydrochlorideOxybuprocaine Hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)Solution / dropsOphthalmicBauch & Lomb Incorporated1995-01-01Not applicableUs
FluressOxybuprocaine Hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)Solution / dropsOphthalmicAkorn1995-02-01Not applicableUs
FluroxOxybuprocaine Hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)SolutionOphthalmicO Cu Soft, Inc.2006-08-302012-02-29Us
FluroxOxybuprocaine Hydrochloride (4 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)SolutionOphthalmicO Cu Soft, Inc.2014-01-29Not applicableUs
International/Other Brands
Benoxil (Santen) / Cebesine (Chauvin Bausch & Lomb) / Conjuncain / Dorsacaine / Lacrimin (Santen) / Novesin (Novartis) / Novesine (Novartis) / Prescaina (Llorens)
Categories
UNII
AXQ0JYM303
CAS number
99-43-4
Weight
Average: 308.4158
Monoisotopic: 308.209992772
Chemical Formula
C17H28N2O3
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=C(N)C=CC(=C1)C(=O)OCCN(CC)CC

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.

TargetActionsOrganism
ASodium channel protein type 10 subunit alpha
inhibitor
Human
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
PathwayCategory
Oxybuprocaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
HyaluronidaseHyaluronidase can cause an increase in the absorption of Oxybuprocaine resulting in an increased serum concentration and potentially a worsening of adverse effects.
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0015029
KEGG Drug
D08319
PubChem Compound
4633
PubChem Substance
46505399
ChemSpider
4472
BindingDB
50017709
ChEBI
309594
ChEMBL
CHEMBL1200
Therapeutic Targets Database
DAP001231
PharmGKB
PA164764617
RxList
RxList Drug Page
Wikipedia
Oxybuprocaine
ATC Codes
S01HA02 — OxybuprocaineD04AB03 — Oxybuprocaine
AHFS Codes
  • 52:16.00 — Local Anesthetics
MSDS
Download (45.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Not Yet RecruitingTreatmentHigh Grade Cervical Intraepithelial Neoplasia / P16 Positive Neoplastic Cells Present1
1, 2Active Not RecruitingTreatmentPancreatic Adenocarcinoma Metastatic / Recurrent Pancreatic Carcinoma / Stage III Pancreatic Cancer / Stage IV Pancreatic Cancer1
1, 2CompletedTreatmentRenal Cell Carcinoma Recurrent / Stage IV Renal Cell Cancer1
1, 2WithdrawnTreatmentAdenocarcinoma of the Pancreas / Colon Adenocarcinoma / Pancreatic Adenocarcinoma Metastatic / Pancreatic Ductal Adenocarcinoma / Rectal Adenocarcinoma / Stage III Pancreatic Cancer / Stage IIIA Colon Cancer / Stage IIIA Rectal Cancer / Stage IIIB Colon Cancer / Stage IIIB Rectal Cancer / Stage IIIC Colon Cancer / Stage IIIC Rectal Cancer / Stage IV Pancreatic Cancer / Stage IVA Colon Cancer / Stage IVA Rectal Cancer / Stage IVB Colon Cancer / Stage IVB Rectal Cancer1
2CompletedTreatmentPancreatic Acinar Cell Carcinoma / Pancreatic Ductal Adenocarcinoma / Recurrent Pancreatic Carcinoma / Stage IV Pancreatic Cancer1
2CompletedTreatmentRecurrent Extragonadal Seminoma / Recurrent Malignant Extragonadal Germ Cell Tumor / Recurrent Malignant Extragonadal Non-Seminomatous Germ Cell Tumor / Recurrent Malignant Testicular Germ Cell Tumor / Recurrent Ovarian Germ Cell Tumor / Stage III Testicular Cancer / Stage IV Extragonadal Non-Seminomatous Germ Cell Tumor / Stage IV Extragonadal Seminoma / Stage IV Ovarian Germ Cell Tumor1
2TerminatedTreatmentRecurrent Colorectal Carcinoma / Stage IVA Colorectal Cancer / Stage IVB Colorectal Cancer1
2, 3RecruitingTreatmentEpstein-Barr Virus Infections / Stage II Nasopharyngeal Carcinoma / Stage III Nasopharyngeal Carcinoma / Stage IVA Nasopharyngeal Carcinoma / Stage IVB Nasopharyngeal Carcinoma1
Not AvailableRecruitingTreatmentMyopia / Refractive Errors1

Pharmacoeconomics

Manufacturers
  • Sola barnes hind
Packagers
  • Akorn Inc.
Dosage forms
FormRouteStrength
SolutionOphthalmic
Solution / dropsOphthalmic
LiquidOphthalmic
Solution / 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.
Patents
Not Available

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000l-2910000000-8a2be292eaed70f08bb5

Taxonomy

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
Aminobenzoic acid or derivatives / Benzoate ester / Aminophenyl ether / Phenoxy compound / Benzoyl / Aniline or substituted anilines / Phenol ether / Alkyl aryl ether / Amino acid or derivatives / Tertiary aliphatic amine
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amino compound, substituted aniline, benzoate ester, amino acid ester (CHEBI:309594)

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 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. [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
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. [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]

Drug created on June 13, 2005 07:24 / Updated on October 23, 2018 21:48