Oxybuprocaine (CED0005629)

Record Information
Version1.0
Creation Date2016-05-25 18:23:29 UTC
Update Date2026-08-19 22:06:03 UTC
Accession NumberCHEM022197
Identification
Common NameOxybuprocaine
ClassSmall Molecule
Description
Oxybuprocaine is an organic compound with the formula C17H28N2O3 and an average molecular weight of 308.42 g/mol. Oxybuprocaine belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as an inhibitor of the protein target Sodium channel protein type 10 subunit alpha (SCN10A). The compound is found in or released from eight recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is used in local anesthetics and antipruritics. Its presence is also noted in food preservation within the food, food processing, and cookware category. In the realm of electrical and electronic equipment, it is associated with electrically stimulated smoking devices and conductors or conductive bodies characterised by the conductive materials. Additionally, it is found in household cleaning and consumer products, specifically in perfumes within detergents and soaps, tobacco smoke filters, and non electric simulated smoking devices. Recorded exposure routes for oxybuprocaine include topical and ophthalmic applications.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
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
Monofree oxybuprocaineKegg
4-Amino-3-butoxy-2-(diethylamino)ethyl ester benzoateGenerator
4-Amino-3-butoxy-benzoate 2-diethylamino-ethyl esterGenerator
Benoxinic acidGenerator
OxibuprocainumHMDB
Benoxinate hydrochlorideHMDB
NovesinHMDB
NovescineHMDB
ButoxyprocaineHMDB
Diethylaminoethyl-4-amino-3-butoxybenzoateHMDB
Benoxinate dihydrochlorideHMDB
Benoxinate monohydrochlorideHMDB
Chemical FormulaC17H28N2O3
Average Molecular Mass308.416 g/mol
Monoisotopic Mass308.210 g/mol
CAS Registry Number99-43-4
IUPAC Name2-(diethylamino)ethyl 4-amino-3-butoxybenzoate
Traditional Nameoxybuprocaine
SMILESCCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC
InChI IdentifierInChI=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
InChI KeyCMHHMUWAYWTMGS-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 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
  • Tertiary amine
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.54 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 Area64.79 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity90.64 m³·mol⁻¹ChemAxon
Polarizability35.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-9320000000-9e6c5bbd587418179c4bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000l-2910000000-8a2be292eaed70f08bb5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4937000000-ef85e92c8ad3ea649c72Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-5930000000-ae6fdd60cca0d58db4ccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9200000000-cfc5e54a39a2628168d8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4489000000-b9c173314aba369f1869Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-4982000000-f6aebe7b807e7905ae5aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4910000000-e4458753a2d193e59118Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-0329000000-83b10169e6afd9c993a3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1952000000-30c42fd5621143767a6bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-4900000000-191d2b6779db0e509f50Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0149000000-438b1ea49968d1d61586Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1941000000-9dca42d9b26a8caec7b6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfu-1910000000-b954ddd41f6af2685bcdNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1102.0Log mg/kg[620:2000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
304AntipruriticsHealthcare, pharmaceuticals & veterinary productsNot Available
401Local anestheticsHealthcare, pharmaceuticals & veterinary productsNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
605Pest RepellantsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)45.8532
Click to view 3D structureCyclic nucleotide-gated channel alpha-1Q00194Bos taurusPredicted (SEA)0.155698
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)32.3853
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)52.159
UDP-3-O-acyl-N-acetylglucosamine deacetylase structureClick to view 3D structureUDP-3-O-acyl-N-acetylglucosamine deacetylaseO67648Aquifex aeolicus (strain VF5)Predicted (SEA)11.5995
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)16.4262
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)200.15
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)272.161
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)79.2505
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)52.2368
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)49.2007
Click to view 3D structurePancreatic alpha-amylaseP00689Rattus norvegicusPredicted (SEA)1.16774
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)348.297
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)244.135
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)254.411
Click to view 3D structureMuscarinic acetylcholine receptor M1Q8WMX0Bos taurusPredicted (SEA)5.13805
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)113.115
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)264.765
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase structureClick to view 3D structure3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseQ15125HumansPredicted (SEA)9.88685
Click to view 3D structureEquilibrative nucleoside transporter 2O54699Rattus norvegicusPredicted (SEA)11.4438
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)313.655
Click to view 3D structureTransient receptor potential cation channel subfamily V member 3Q8K424Mus musculusPredicted (SEA)35.8106
Click to view 3D structureC-8 sterol isomerase ERG2P32352Baker's yeastPredicted (SEA)6.30579
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1385.79
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)939.095
Concentrations
Not Available
External Links
DrugBank IDDB00892
HMDB IDHMDB0015029
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxybuprocaine
Chemspider ID4472
ChEBI ID309594
PubChem Compound ID4633
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25360701
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=3598888
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6621359
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8214534
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=9013953
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9989796