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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:39 UTC
HMDB IDHMDB0014945
Secondary Accession Numbers
  • HMDB14945
Metabolite Identification
Common NameProparacaine
DescriptionProparacaine is only found in individuals that have used or taken this drug. It is a topical anesthetic drug of the amino ester group. It is available as its hydrochloride salt in ophthalmic solutions at a concentration of 0.5%. [Wikipedia]The exact mechanism whereby proparacaine and other local anesthetics influence the permeability of the cell membrane is unknown; however, several studies indicate that local anesthetics may limit sodium ion permeability through the lipid layer of the nerve cell membrane. Proparacaine may alter epithelial sodium channels through interaction with channel protein residues. This limitation prevents the fundamental change necessary for the generation of the action potential.
Structure
Data?1582753239
Synonyms
ValueSource
ProxymetacaineKegg
ProssimetacainaHMDB
ProximetacainumHMDB
OphtheticHMDB
ParcaineHMDB
AlcaineHMDB
Ocu-caineHMDB
Proxymetacaine hydrochlorideHMDB
AK-taineHMDB
KainairHMDB
ProxymethacaineHMDB
Chibro-kerakainHMDB
KéracaineHMDB
Minims proxymetacaine hydrochlorideHMDB
OphthaineHMDB
Proparakain-posHMDB
Proxymetacaine monohydrochlorideHMDB
Proparacaine hydrochlorideMeSH
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoateMeSH
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl esterMeSH
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate monohydrochlorideMeSH
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochloride*benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochlorideMeSH
Proparacaine HCLMeSH
Chemical FormulaC16H26N2O3
Average Molecular Weight294.3892
Monoisotopic Molecular Weight294.194342708
IUPAC Name2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
Traditional Nameproparacaine
CAS Registry Number499-67-2
SMILES
CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC
InChI Identifier
InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
InChI KeyKCLANYCVBBTKTO-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 effect

Health effect:

Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182 - 183.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.39 g/LNot Available
LogP2.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.39 g/LALOGPS
logP2.97ALOGPS
logP2.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.79 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity86.04 m³·mol⁻¹ChemAxon
Polarizability34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9320000000-1725fcdf405f1285cf5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f6t-0590000000-0aae7080739b3c83b4a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-3790000000-19484885f2060a30ee39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-6940000000-b6eb0be7d6e42c79f6d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-8b40ab2bb2e6ca190ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2490000000-e0dd5d94666e639cd15fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-3890000000-83f45f2c670646cf13b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4910000000-080bada57e1dc3ab313cSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00807 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00807 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00807
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4766
KEGG Compound IDC07383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProxymetacaine
METLIN IDNot Available
PubChem Compound4935
PDB IDNot Available
ChEBI ID309007
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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. Tella SR, Goldberg SR: Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12. [PubMed:9476974 ]