Identification
- Summary
Proparacaine is a topical anesthetic used for ophthalmic practice.
- Brand Names
- Alcaine
- Generic Name
- Proparacaine
- DrugBank Accession Number
- DB00807
- Background
Proparacaine is a topical anesthetic drug of the amino ester group. It is found in ophthalmic solutions at a concentration of 0.5% as the hydrochloride salt.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Proparacaine (DB00807)
- Weight
- Average: 294.3892
Monoisotopic: 294.194342708 - Chemical Formula
- C16H26N2O3
- Synonyms
- Proximetacaina
- Proxymetacaine
- Proxymetacainum
Pharmacology
- Indication
Used as a local (ophthalmic) anesthetic.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism ASodium channel protein type 10 subunit alpha inhibitorHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Proparacaine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Proparacaine. Abiraterone The risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Proparacaine. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Proparacaine. Acetazolamide The risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Proparacaine. Acetic acid The risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Proparacaine. Acetyl sulfisoxazole The risk or severity of methemoglobinemia can be increased when Acetyl sulfisoxazole is combined with Proparacaine. Adagrasib The risk or severity of methemoglobinemia can be increased when Adagrasib is combined with Proparacaine. Afatinib The risk or severity of methemoglobinemia can be increased when Afatinib is combined with Proparacaine. Aldesleukin The risk or severity of methemoglobinemia can be increased when Aldesleukin is combined with Proparacaine. Alectinib The risk or severity of methemoglobinemia can be increased when Alectinib is combined with Proparacaine. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Proparacaine hydrochloride U96OL57GOY 5875-06-9 BFUUJUGQJUTPAF-UHFFFAOYSA-N - International/Other Brands
- Ak-Taine / Diocaine / Ocu-Caine / Ophthaine / Spectro-Caine
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alcaine Solution / drops 0.5 % w/v Ophthalmic Alcon, Inc. 1971-12-31 Not applicable Canada 
Ophthetic Solution / drops .5 % Ophthalmic Allergan 1964-12-31 2011-08-04 Canada Ophthetic Solution 5 mg/1mL Ophthalmic Physicians Total Care, Inc. 1996-06-17 2012-06-30 US 
Ophthetic Solution 5 mg/1mL Ophthalmic Allergan 1996-01-01 2009-09-03 US Proparacaine Solution 0.5 % Ophthalmic Pharma Stulln Inc. 1994-12-31 Not applicable Canada R.O.-parcaine Dps 5mg/ml Solution / drops 5 mg / mL Ophthalmic Richmond Pharmaceuticals Inc. 1993-12-31 1997-08-11 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alcaine Solution / drops 5 mg/1mL Ophthalmic A-S Medication Solutions 1973-10-19 2016-05-31 US Alcaine Solution / drops 5 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1973-10-19 Not applicable US Odan-proparacaine Solution .5 % Ophthalmic Odan Laboratories Ltd 1985-12-31 Not applicable Canada PMS-proparacaine Hydrochloride Oph Soltn 0.5% Solution / drops .5 % Ophthalmic Pharmascience Inc 1992-12-31 1996-09-10 Canada Proparacaine Hydrochloride Solution / drops 5 mg/1mL Ophthalmic Nucare Pharmaceuticals,inc. 1995-09-29 Not applicable US Proparacaine Hydrochloride Solution / drops 5 mg/1mL Ophthalmic A S Medication Solutions 2000-03-16 2013-07-03 US Proparacaine Hydrochloride Solution / drops 5 mg/1mL Ophthalmic Henry Schein Inc. 2015-05-13 Not applicable US Proparacaine Hydrochloride Solution / drops 5 mg/1mL Ophthalmic Preferred Pharmaceuticals, Inc. 2014-04-28 2019-11-12 US Proparacaine Hydrochloride Solution 5 mg/1mL Ophthalmic Rebel Distributors 1995-09-29 Not applicable US Proparacaine Hydrochloride Solution / drops 5 mg/1mL Ophthalmic Sandoz Inc. 2000-06-05 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ALCAINE STERILE OPHTHALMIC SOLUTION 0.5% Solution 0.5 % Ophthalmic ALCON PTE LTD 1990-06-13 Not applicable Singapore - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Odan-fluoracaine Proparacaine hydrochloride (0.5 %) + Fluorescein sodium (0.25 %) Solution Ophthalmic Odan Laboratories Ltd 1986-12-31 Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Flucaine Proparacaine hydrochloride (5 mg/1mL) + Fluorescein sodium (2.5 mg/1mL) Solution / drops Ophthalmic OCuSOFT, INC. 1989-03-30 2019-07-16 US Fluorescein Sodium and Proparacaine Hydrochloride Proparacaine hydrochloride (5 mg/1mL) + Fluorescein sodium (2.5 mg/1mL) Solution / drops Ophthalmic Altaire Pharmaceuticals Inc. 2000-06-14 Not applicable US Mydriatic-4 Proparacaine hydrochloride (5 mg/1mL) + Ketorolac tromethamine (5 mg/1mL) + Phenylephrine hydrochloride (25 mg/1mL) + Tropicamide (10 mg/1mL) Solution / drops Ophthalmic Imprimis Njof, Llc 2018-05-01 Not applicable US
Categories
- ATC Codes
- S01HA04 — Proxymetacaine
- Drug Categories
- Acids, Carbocyclic
- Aminobenzoates
- Anesthetics
- Anesthetics, Local
- Benzene Derivatives
- Benzoates
- Central Nervous System Agents
- Central Nervous System Depressants
- Ethers
- Hydroxy Acids
- Hydroxybenzoate Ethers
- Hydroxybenzoates
- Isomerism
- Local Anesthesia
- Ophthalmologicals
- para-Aminobenzoates
- Peripheral Nervous System Agents
- Phenols
- Phenyl Ethers
- Sensory Organs
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- 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
- Alkyl aryl ether / Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aminophenyl ether / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carboxylic acid derivative show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- benzoate ester (CHEBI:8485)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- B4OB0JHI1X
- CAS number
- 499-67-2
- 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
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
- 50225500
- 34905
- ChEBI
- 8485
- ChEMBL
- CHEMBL1196
- ZINC
- ZINC000001530762
- Therapeutic Targets Database
- DAP000513
- PharmGKB
- PA164776849
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Proxymetacaine
- FDA label
- Download (118 KB)
- MSDS
- Download (73.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Health Services Research Pupils unequal 1 4 Recruiting Supportive Care Astigmatism / Hypermetropia / Myopia (Disorder) / Refractive Errors 1 4 Recruiting Treatment Dacryocystitis / Dacryostenosis / Epiphora 1 4 Terminated Treatment Dacryocystitis / Dacryostenosis / Epiphora 1 3 Completed Supportive Care Local Anaesthesia therapy 1 3 Completed Treatment Pain 1 1 Completed Treatment Corneal Abrasions 1 Not Available Completed Not Available Bradycardia / Nausea / Pain / Strabismus 1 Not Available Completed Diagnostic Post Operative Nausea and Vomiting (PONV) / Postoperative pain / Vitreoretinal Surgery 1 Not Available Completed Other Age - Related Macular Degeneration (AMD) / Diabetic Macular Edema (DME) / Infection at the site of injection / Injection Site / Postoperative pain 1
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
Form Route Strength Solution / drops Ophthalmic 0.5 % w/v Solution Ophthalmic 5 mg Solution / drops Ophthalmic Solution / drops Ophthalmic Solution Ophthalmic Solution Ophthalmic .5 % Solution / drops Ophthalmic .5 % Solution Ophthalmic 5.0 mg/ml Solution Ophthalmic 0.5 % Solution Ophthalmic 5 mg/1mL Solution / drops Ophthalmic 5 mg/1mL Solution / drops Ophthalmic 5 mg / mL - Prices
Unit description Cost Unit Proparacaine hcl powder 84.0USD g Proparacaine HCl 0.5% Solution 15ml Bottle 14.99USD bottle Alcaine 0.5% eye drops 2.19USD ml Proparacaine 0.5% eye drops 1.27USD ml Ophthetic 0.5% eye drops 1.02USD ml Alcaine 0.5 % Solution 0.68USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 182-183.3 °C Not Available water solubility Soluble Not Available logP 2.5 Not Available pKa 3.2 Not Available - Predicted Properties
Property Value Source Water Solubility 1.39 mg/mL ALOGPS logP 2.97 ALOGPS logP 2.6 Chemaxon logS -2.3 ALOGPS pKa (Strongest Basic) 8.96 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 64.79 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 86.04 m3·mol-1 Chemaxon Polarizability 34 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9769 Blood Brain Barrier + 0.8876 Caco-2 permeable + 0.6501 P-glycoprotein substrate Substrate 0.7085 P-glycoprotein inhibitor I Non-inhibitor 0.7586 P-glycoprotein inhibitor II Non-inhibitor 0.9645 Renal organic cation transporter Non-inhibitor 0.7172 CYP450 2C9 substrate Non-substrate 0.8202 CYP450 2D6 substrate Non-substrate 0.5953 CYP450 3A4 substrate Substrate 0.5624 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9093 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5247 Ames test Non AMES toxic 0.7542 Carcinogenicity Non-carcinogens 0.7336 Biodegradation Not ready biodegradable 0.9764 Rat acute toxicity 2.5543 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8356 hERG inhibition (predictor II) Non-inhibitor 0.5406
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0f6t-0590000000-0aae7080739b3c83b4a4
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 03, 2023 08:16