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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:50 UTC
HMDB IDHMDB0015029
Secondary Accession Numbers
  • HMDB15029
Metabolite Identification
Common NameOxybuprocaine
DescriptionOxybuprocaine 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 impulses.
Structure
Data?1582753249
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 Weight308.4158
Monoisotopic Molecular Weight308.209992772
IUPAC Name2-(diethylamino)ethyl 4-amino-3-butoxybenzoate
Traditional Nameoxybuprocaine
CAS Registry Number99-43-4
SMILES
CCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC
InChI Identifier
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
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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point216.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.54 g/LNot Available
LogP3.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.67631661259
DarkChem[M-H]-171.26631661259
DeepCCS[M+H]+177.70830932474
DeepCCS[M-H]-175.3530932474
DeepCCS[M-2H]-208.23530932474
DeepCCS[M+Na]+183.80130932474
AllCCS[M+H]+176.532859911
AllCCS[M+H-H2O]+173.632859911
AllCCS[M+NH4]+179.232859911
AllCCS[M+Na]+180.032859911
AllCCS[M-H]-176.432859911
AllCCS[M+Na-2H]-177.232859911
AllCCS[M+HCOO]-178.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxybuprocaineCCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC3555.5Standard polar33892256
OxybuprocaineCCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC2480.3Standard non polar33892256
OxybuprocaineCCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC2457.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxybuprocaine,1TMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N[Si](C)(C)C2578.0Semi standard non polar33892256
Oxybuprocaine,1TMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N[Si](C)(C)C2529.2Standard non polar33892256
Oxybuprocaine,1TMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N[Si](C)(C)C3120.9Standard polar33892256
Oxybuprocaine,2TMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N([Si](C)(C)C)[Si](C)(C)C2521.7Semi standard non polar33892256
Oxybuprocaine,2TMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N([Si](C)(C)C)[Si](C)(C)C2564.5Standard non polar33892256
Oxybuprocaine,2TMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N([Si](C)(C)C)[Si](C)(C)C2856.6Standard polar33892256
Oxybuprocaine,1TBDMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N[Si](C)(C)C(C)(C)C2749.3Semi standard non polar33892256
Oxybuprocaine,1TBDMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N[Si](C)(C)C(C)(C)C2743.1Standard non polar33892256
Oxybuprocaine,1TBDMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N[Si](C)(C)C(C)(C)C3186.8Standard polar33892256
Oxybuprocaine,2TBDMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2914.6Semi standard non polar33892256
Oxybuprocaine,2TBDMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2909.8Standard non polar33892256
Oxybuprocaine,2TBDMS,isomer #1CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3032.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxybuprocaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9320000000-9e6c5bbd587418179c4b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxybuprocaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybuprocaine , positive-QTOFsplash10-000l-2910000000-8a2be292eaed70f08bb52017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 10V, Positive-QTOFsplash10-0a4i-4937000000-ef85e92c8ad3ea649c722016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 20V, Positive-QTOFsplash10-0zfr-5930000000-ae6fdd60cca0d58db4cc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 40V, Positive-QTOFsplash10-0a4i-9200000000-cfc5e54a39a2628168d82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 10V, Negative-QTOFsplash10-0a4i-4489000000-b9c173314aba369f18692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 20V, Negative-QTOFsplash10-0pb9-4982000000-f6aebe7b807e7905ae5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 40V, Negative-QTOFsplash10-0a4i-4910000000-e4458753a2d193e591182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 10V, Positive-QTOFsplash10-0pb9-0329000000-83b10169e6afd9c993a32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 20V, Positive-QTOFsplash10-0udi-1952000000-30c42fd5621143767a6b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 40V, Positive-QTOFsplash10-0udr-4900000000-191d2b6779db0e509f502021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 10V, Negative-QTOFsplash10-0a4i-0149000000-438b1ea49968d1d615862021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 20V, Negative-QTOFsplash10-0udi-1941000000-9dca42d9b26a8caec7b62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybuprocaine 40V, Negative-QTOFsplash10-0zfu-1910000000-b954ddd41f6af2685bcd2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00892 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00892 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00892
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4472
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxybuprocaine
METLIN IDNot Available
PubChem Compound4633
PDB IDNot Available
ChEBI ID309594
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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 ]