Oxybuprocaine

Common Name

Oxybuprocaine Description

Oxybuprocaine is only found in individuals that have used or taken this drug. It is a local anesthetic, which is used especially in ophthalmology and otolaryngology. 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 implises. Structure

Synonyms

Value Source 4-amino-3-Butoxy-2-(diethylamino)ethyl ester benzoic acidChEBI 4-amino-3-Butoxy-benzoic acid 2-diethylamino-ethyl esterChEBI 4-amino-3-N-Butoxy-benzoesaeure-diaethylaminoaethylesterChEBI BenoxilChEBI BenoxinateChEBI ButoxyaminobenzoyldiethylaminoethanolChEBI OxbarukainChEBI OxibuprocainaChEBI OxibuprokainChEBI OxybucaineChEBI OxybuprocainumChEBI OxyriprocaineChEBI 4-amino-3-Butoxy-2-(diethylamino)ethyl ester benzoateGenerator 4-amino-3-Butoxy-benzoate 2-diethylamino-ethyl esterGenerator Benoxinic acidGenerator OxibuprocainumHMDB Benoxinate hydrochlorideMeSH NovesinMeSH NovescineMeSH ButoxyprocaineMeSH Diethylaminoethyl-4-amino-3-butoxybenzoateMeSH Benoxinate dihydrochlorideMeSH Benoxinate monohydrochlorideMeSH

Chemical Formlia

C₁₇H₂₈N₂O₃ Average Molecliar Weight

308.4158 Monoisotopic Molecliar Weight

308.209992772 IUPAC Name

2-(diethylamino)ethyl 4-amino-3-butoxybenzoate Traditional Name

oxybuprocaine CAS Registry Number

99-43-4 SMILES

InChI Identifier

InChI Key

CMHHMUWAYWTMGS-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as benzoic acid esters. These are ester derivatives of benzoic acid. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted 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

Primary aromatic amines

Trialkylamines

Carboxylic acid esters

Amino acids and derivatives

Monocarboxylic acids and derivatives

Organopnictogen compounds

Organic oxides

Hydrocarbon derivatives

Substituents

Aminobenzoic acid or derivatives

Benzoate ester

Aminophenyl ether

Phenoxy compound

Benzoyl

Phenol ether

Aniline or substituted anilines

Alkyl aryl ether

Primary aromatic amine

Tertiary aliphatic amine

Tertiary amine

Carboxylic acid ester

Amino acid or derivatives

Carboxylic acid derivative

Ether

Monocarboxylic acid or derivatives

Organopnictogen compound

Primary amine

Organic oxygen compound

Amine

Organic nitrogen compound

Hydrocarbon derivative

Organic oxide

Organonitrogen compound

Organooxygen compound

Aromatic homomonocyclic compound

Molecliar Framework

Aromatic homomonocyclic compounds External Descriptors

tertiary amino compound (CHEBI:309594 )

substituted aniline (CHEBI:309594 )

benzoate ester (CHEBI:309594 )

amino acid ester (CHEBI:309594 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Anesthetics, Local

Application

Pharmaceutical

Cellliar locations

Cytoplasm

Extracellliar

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point216.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility5.44e-01 g/LNot Available LogP3.1Not Available

Predicted Properties

Property Value Source Water Solubility0.54 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 ŲChemAxon Rotatable Bond Count11ChemAxon Refractivity90.64 m³·mol^-1ChemAxon Polarizability35.83 ųChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-000l-2910000000-8a2be292eaed70f08bb5View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Cytoplasm

Extracellliar

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Name SMPDB Link KEGG Link Oxybuprocaine PathwaySMP00400Not Available

Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00892

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00892

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB00892 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

4472 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Oxybuprocaine NuGOwiki Link

HMDB15029 Metagene Link

HMDB15029 METLIN ID

Not Available PubChem Compound

4633 PDB ID

Not Available ChEBI ID

309594

Product: TAS-104

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

Enzymes

General function:

Involved in carboxylesterase activity

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

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 ]

General function:

Involved in ion channel activity

Specific function:

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

Gene Name:

SCN10A

Uniprot ID:

Q9Y5Y9

Molecular weight:

220623.6

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 ]

PMID: 21821707

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