Identification

Name
Proparacaine
Accession Number
DB00807  (APRD00522)
Type
Small Molecule
Groups
Approved, 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%.

Structure
Thumb
Synonyms
  • Proximetacaina
  • Proxymetacaine
  • Proxymetacainum
Product Ingredients
IngredientUNIICASInChI Key
Proparacaine hydrochlorideU96OL57GOY5875-06-9BFUUJUGQJUTPAF-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlcaineSolution / drops0.5 %OphthalmicNovartis1971-12-31Not applicableCanada
OphtheticSolution5 mg/1mLOphthalmicAllergan1996-01-012009-09-03Us
OphtheticSolution5 mg/1mLOphthalmicPhysicians Total Care, Inc.1996-06-172012-06-30Us
OphtheticSolution / drops.5 %OphthalmicAllergan1964-12-312011-08-04Canada
ProparacaineLiquid0.5 %Ophthalmic; TopicalEberth Pharmaceuticals Inc1994-12-31Not applicableCanada
R.O.-parcaine Dps 5mg/mlSolution / drops5 mgOphthalmicRichmond Pharmaceuticals1993-12-311997-08-11Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlcaineSolution / drops5 mg/1mLOphthalmicA-S Medication Solutions1973-10-192016-05-31Us
AlcaineSolution / drops5 mg/1mLOphthalmicAlcon, Inc.1973-10-19Not applicableUs
Odan-proparacaineSolution.5 %Ophthalmic; TopicalOdan Laboratories Ltd1985-12-31Not applicableCanada
PMS-proparacaine Hydrochloride Oph Soltn 0.5%Solution / drops.5 %OphthalmicPharmascience Inc1992-12-311996-09-10Canada
Proparacaine HydrochlorideSolution / drops5 mg/1mLOphthalmicNucare Pharmaceuticals,inc.1995-09-29Not applicableUs
Proparacaine HydrochlorideSolution / drops5 mg/1mLOphthalmicH.J. Harkins Company1995-09-29Not applicableUs
Proparacaine HydrochlorideSolution / drops5 mg/1mLOphthalmicPreferreed Pharmaceuticals Inc.2014-04-28Not applicableUs
Proparacaine HydrochlorideSolution / drops5 mg/1mLOphthalmicSandoz2000-06-05Not applicableUs
Proparacaine HydrochlorideSolution / drops5 mg/1mLOphthalmicA-S Medication Solutions2000-06-05Not applicableUs
Proparacaine HydrochlorideSolution / drops5 mg/1mLOphthalmicA S Medication Solutions2000-03-16Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Odan-fluoracaineProparacaine hydrochloride (0.5 %) + Fluorescein sodium (0.25 %)SolutionOphthalmicOdan Laboratories Ltd1986-12-31Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FlucaineProparacaine hydrochloride (5 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)Solution / dropsOphthalmicO Cu Soft, Inc.1989-03-30Not applicableUs
Fluorescein Sodium and Proparacaine HydrochlorideProparacaine hydrochloride (5 mg/1mL) + Fluorescein sodium (2.5 mg/1mL)Solution / dropsOphthalmicAltaire Pharmaceuticals Inc.2000-06-14Not applicableUs
Mydriatic-4Proparacaine hydrochloride (5 mg/1mL) + Ketorolac tromethamine (5 mg/1mL) + Phenylephrine hydrochloride (25 mg/1mL) + Tropicamide (10 mg/1mL)Solution / dropsOphthalmicImprimis Njof, Llc2018-05-01Not applicableUs
International/Other Brands
Ak-Taine / Diocaine / Ocu-Caine / Ophthaine / Ophthetic / Spectro-Caine
Categories
UNII
B4OB0JHI1X
CAS number
499-67-2
Weight
Average: 294.3892
Monoisotopic: 294.194342708
Chemical Formula
C16H26N2O3
InChI Key
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

Pharmacology

Indication

Used as a local (ophthalmic) anesthetic.

Associated Therapies
Pharmacodynamics

Proparacaine 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 action

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.

TargetActionsOrganism
ASodium channel protein type 10 subunit alpha
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Plasma

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Proparacaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
HyaluronidaseHyaluronidase can cause an increase in the absorption of Proparacaine resulting in an increased serum concentration and potentially a worsening of adverse effects.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014945
KEGG Drug
D08448
KEGG Compound
C07383
PubChem Compound
4935
PubChem Substance
46507960
ChemSpider
4766
BindingDB
50017718
ChEBI
8485
ChEMBL
CHEMBL1196
Therapeutic Targets Database
DAP000513
PharmGKB
PA164776849
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Proparacaine
ATC Codes
S01HA04 — Proxymetacaine
AHFS Codes
  • 52:16.00 — Local Anesthetics
FDA label
Download (118 KB)
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentPain NOS1
Not AvailableCompletedNot AvailableBradycardia / Nausea / Pain NOS / Strabismus1
Not AvailableCompletedDiagnosticPost-Operative Nausea and Vomiting (PONV) / Postoperative pain / Postoperative; Parotitis / Vitreoretinal Surgery1
Not AvailableCompletedSupportive CareAnaesthesia therapy / Cataract Unilateral Pending Extraction1
Not AvailableCompletedTreatmentCataracts2
Not AvailableRecruitingOtherAge-Related Macular Degeneration (ARMD) / Diabetic Macular Edema (DME) / Injection Site / Injection site infection / Postoperative pain1
Not AvailableRecruitingTreatmentGlaucoma, Angle-Closure1
Not AvailableRecruitingTreatmentMyopia / Refractive Errors1
Not AvailableRecruitingTreatmentPerioperative Pain Experiences1
Not AvailableTerminatedSupportive CarePain NOS / Retinopathy of Prematurity1
Not AvailableUnknown StatusTreatmentMacular Degeneration1

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
  • Accutome Inc.
  • Akorn Inc.
  • Alcon Laboratories
  • Allergan Inc.
  • Altaire Pharmaceuticals
  • A-S Medication Solutions LLC
  • Bausch & Lomb Inc.
  • Conta Care Ophthalmics and Diagnostics
  • Deca Pharmaceuticals LLC
  • Diversified Healthcare Services Inc.
  • Eye Care and Cure Corp.
  • Eye Supply Usa Inc.
  • Falcon Pharmaceuticals Ltd.
  • Medical Ophthalmics
  • MWI Veterinary Supply Co.
  • Ocusoft
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Professional Co.
  • Rx Veterinary Products
  • Stat Rx Usa
  • Wa Butler Co.
  • Wilson Ophthalmic Corp.
Dosage forms
FormRouteStrength
Solution / dropsOphthalmic0.5 %
Solution / dropsOphthalmic
SolutionOphthalmic
SolutionOphthalmic; Topical.5 %
Solution / dropsOphthalmic.5 %
LiquidOphthalmic; Topical0.5 %
SolutionOphthalmic5 mg/1mL
Solution / dropsOphthalmic5 mg/1mL
Solution / dropsOphthalmic5 mg
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)182-183.3 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f6t-0590000000-0aae7080739b3c83b4a4

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acid esters
Alternative Parents
Aminobenzoic acids and derivatives / Aminophenyl ethers / Phenoxy compounds / Benzoyl derivatives / Aniline and substituted anilines / Alkyl aryl ethers / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives
show 4 more
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
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzoate ester (CHEBI:8485)

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 acro...
Gene Name
SCN10A
Uniprot ID
Q9Y5Y9
Uniprot Name
Sodium channel protein type 10 subunit alpha
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]

Drug created on June 13, 2005 07:24 / Updated on October 23, 2018 21:48