Proparacaine (T3D2896)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2009-07-21 20:27:41 UTC
Update Date2014-12-24 20:25:53 UTC
Accession NumberT3D2896
Identification
Common NameProparacaine
ClassSmall Molecule
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.
Compound Type
  • Amine
  • Anesthetic, Local
  • Drug
  • Ester
  • Ether
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Ak-Taine
Alcaine
Diocaine
Ocu-Caine
Ophthaine
Ophthetic
Prossimetacaina
Proximetacaina
Proximetacainum
Proxymetacaine
Proxymetacainum
Spectro-Caine
Chemical FormulaC16H26N2O3
Average Molecular Mass294.389 g/mol
Monoisotopic Mass294.194 g/mol
CAS Registry Number499-67-2
IUPAC Name2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
Traditional Nameproparacaine
SMILESCCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC
InChI IdentifierInChI=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 KeyInChIKey=KCLANYCVBBTKTO-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
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Proparacaine PathwayNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point182-183.3°C
Boiling PointNot Available
Solubility1.39e+00 g/L
LogP2.5
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9320000000-1725fcdf405f1285cf5f2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f6t-0590000000-0aae7080739b3c83b4a42017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-3790000000-19484885f2060a30ee392016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-6940000000-b6eb0be7d6e42c79f6d22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-8b40ab2bb2e6ca190ac62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2490000000-e0dd5d94666e639cd15f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-3890000000-83f45f2c670646cf13b42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4910000000-080bada57e1dc3ab313c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0940000000-dd6bde086183731626072021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2950000000-6cf937b31cea35f9327a2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-2900000000-74d2433c695036dfb8f52021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-6934514b2f05a7f1e0432021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-2930000000-d9841e3d4745b761afc52021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-0900000000-acfb0c0e342bd2f577c82021-10-11View Spectrum
Toxicity Profile
Route of ExposureTopical (eye drop).
Mechanism of ToxicityThe 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.
MetabolismPlasma
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as an ophthalmic anesthetic (as eye drops) to reduce pain and discomfort during procedures involving the eye. [Wikipedia]
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsDizziness or drowsiness; increased sweating; irregular heartbeat; muscle twitching or trembling; nausea or vomiting; shortness of breath or troubled breathing; unusual excitement, nervousness, or restlessness; unusual tiredness or weakness. Burning, stinging, redness, or other irritation of eye. (1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00807
HMDB IDHMDB14945
PubChem Compound ID4935
ChEMBL IDCHEMBL1196
ChemSpider ID4766
KEGG IDC07383
UniProt IDNot Available
OMIM ID
ChEBI ID309007
BioCyc IDNot Available
CTD IDNot Available
Stitch IDProparacaine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkProparacaine
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Sodium channel protein type 10 subunit alpha
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 across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
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. [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. [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. [9476974 ]
Target Details
2. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]