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Identification
NameProparacaine
Accession NumberDB00807  (APRD00522)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

Proparacaine 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]

Structure
Thumb
Synonyms
Proparacaine
Proximetacaina
Proxymetacaine
Proxymetacainum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alcainesolution/ drops5 mg/mLophthalmicAlcon Laboratories, Inc.1973-10-19Not applicableUs
Proparacaine Hydrochloridesolution/ drops5 mg/mLophthalmicHenry Schein Inc.2015-05-13Not applicableUs
Proparacaine Hydrochloridesolution/ drops5 mg/mLophthalmicBausch & Lomb Incorporated1995-09-29Not applicableUs
Proparacaine Hydrochloridesolution5 mg/mLophthalmicRebel Distributors Corp1995-09-29Not applicableUs
Proparacaine Hydrochloridesolution/ drops5 mg/mLophthalmicAkorn, Inc.2000-03-16Not applicableUs
Proparacaine Hydrochloridesolution/ drops5 mg/mLophthalmicPreferred Pharmaceuticals, Inc.2014-04-28Not applicableUs
Proparacaine Hydrochloridesolution5 mg/mLophthalmicSTAT Rx USA LLC2000-06-05Not applicableUs
Proparacaine Hydrochloridesolution/ drops5 mg/mLophthalmicSandoz Inc.2000-06-05Not applicableUs
Proparacaine Hydrochloridesolution/ drops5 mg/mLophthalmicMwi2015-03-27Not applicableUs
Proparacaine Hydrochloridesolution/ drops5 mg/mLophthalmicA S Medication Solutions Llc2000-03-16Not applicableUs
Proparacaine Hydrochloridesolution/ drops5 mg/mLophthalmicH.J. Harkins Company, Inc.1995-09-29Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Ak-TaineNot Available
DiocaineNot Available
Ocu-CaineNot Available
OphthaineNot Available
OphtheticNot Available
Spectro-CaineNot Available
Brand mixtures
NameLabellerIngredients
FlucaineO Cu Soft, Inc.
Fluorescein Sodium and Proparacaine HydrochlorideAltaire Pharmaceuticals Inc.
Salts
Name/CASStructureProperties
Proparacaine Hydrochloride
Thumb
  • InChI Key: BFUUJUGQJUTPAF-UHFFFAOYSA-N
  • Monoisotopic Mass: 330.171020447
  • Average Mass: 330.85
DBSALT000459
Categories
UNIIB4OB0JHI1X
CAS number499-67-2
WeightAverage: 294.3892
Monoisotopic: 294.194342708
Chemical FormulaC16H26N2O3
InChI KeyInChIKey=KCLANYCVBBTKTO-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
SMILES
CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC
Taxonomy
DescriptionThis compound 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
  • Benzoate ester
  • Aminobenzoic acid or derivatives
  • Benzylether
  • Substituted aniline
  • Phenol ether
  • Benzoyl
  • Aniline
  • Alkyl aryl ether
  • Primary aromatic amine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as a local (ophthalmic) anesthetic.
PharmacodynamicsProparacaine stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses thereby effecting local anesthetic action. More specifically, proparacaine appears to bind or antagonize the function of voltage gated sodium channels.
Mechanism of actionThe 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Plasma

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Proparacaine Action PathwayDrug actionSMP00403
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9769
Blood Brain Barrier+0.8876
Caco-2 permeable+0.6501
P-glycoprotein substrateSubstrate0.7085
P-glycoprotein inhibitor INon-inhibitor0.7586
P-glycoprotein inhibitor IINon-inhibitor0.9645
Renal organic cation transporterNon-inhibitor0.7172
CYP450 2C9 substrateNon-substrate0.8202
CYP450 2D6 substrateNon-substrate0.5953
CYP450 3A4 substrateSubstrate0.5624
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9093
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5247
Ames testNon AMES toxic0.7542
CarcinogenicityNon-carcinogens0.7336
BiodegradationNot ready biodegradable0.9764
Rat acute toxicity2.5543 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8356
hERG inhibition (predictor II)Non-inhibitor0.5406
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Alcon laboratories inc
  • Pharmafair inc
  • Apothecon inc div bristol myers squibb
  • Allergan pharmaceutical
  • Optopics laboratories corp
  • Bausch and lomb pharmaceuticals inc
  • Sola barnes hind
  • Taylor pharmacal co
Packagers
Dosage forms
FormRouteStrength
Solution/ dropsophthalmic
Solutionophthalmic5 mg/mL
Solution/ dropsophthalmic5 mg/mL
Prices
Unit descriptionCostUnit
Proparacaine hcl powder84.0USD g
Proparacaine HCl 0.5% Solution 15ml Bottle14.99USD bottle
Alcaine 0.5% eye drops2.19USD ml
Proparacaine 0.5% eye drops1.27USD ml
Ophthetic 0.5% eye drops1.02USD ml
Alcaine 0.5 % Solution0.68USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point182-183.3 °CNot Available
water solubilitySolubleNot Available
logP2.5Not Available
pKa3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.39 mg/mLALOGPS
logP2.97ALOGPS
logP2.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.79 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity86.04 m3·mol-1ChemAxon
Polarizability34 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesS01HA04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (118 KB)
MSDSDownload (73.7 KB)
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
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. [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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23