Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H26N2O3 |
Molecular Weight | 294.3892 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC
InChI
InChIKey=KCLANYCVBBTKTO-UHFFFAOYSA-N
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
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%. Proparacaine hydrochloride ophthalmic solution is indicated for procedures in which a topical ophthalmic anesthetic is indicated: corneal anesthesia of short duration, e.g. tonometry, gonioscopy, removal of corneal foreign bodies, and for short corneal and conjunctival procedures. 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. 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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2096682 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2579237 |
1.9 µM [IC50] | ||
Target ID: CHEMBL5451 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.drugs.com/pro/proparacaine.html |
Primary | Alcaine Approved UseALCAINE® ophthalmic solution is indicated for procedures in which a topical ophthalmic anesthetic is indicated: corneal anesthesia of short duration, e.g. tonometry, gonioscopy, removal of corneal foreign bodies, and for short corneal and conjunctival procedures. Launch Date1953 |
PubMed
Title | Date | PubMed |
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Subtenon lidocaine vs topical proparacaine in adult strabismus surgery. | 2006 Fall |
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Calcium-binding protein calretinin immunoreactivity in the dog superior colliculus. | 2006 Oct 30 |
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Secretory leukocyte protease inhibitor is an inducible antimicrobial peptide expressed in Staphylococcus aureus endophthalmitis. | 2007 |
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Topical anesthesia in transconjunctival sutureless 25-gauge vitrectomy for macular-based disorders. | 2007 |
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Assisted local anaesthesia for endoscopic dacryocystorhinostomy. | 2007 Apr |
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Posterior vitrectomy under topical anesthesia. | 2007 Apr |
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[Self-medication with local anaesthetics by glaucoma patients using teletonometry]. | 2007 Dec |
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Effect of proparacaine on central corneal thickness values: an evaluation using noncontact specular microscopy and pentacam. | 2007 Jan |
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Topical anaesthesia alone versus topical anaesthesia with intracameral lidocaine for phacoemulsification. | 2007 Jul 18 |
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Prevalence of feline herpesvirus 1, Chlamydophila felis, and Mycoplasma spp DNA in conjunctival cells collected from cats with and without conjunctivitis. | 2007 Jun |
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Laser photocoagulation combined with intravitreal triamcinolone acetonide injection in proliferative diabetic retinopathy with macular edema. | 2007 Mar |
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An assessment of the discomfort associated with the use of rose bengal 1% eyedrops on the normal human eye: a comparison with saline 0.9% and a topical ocular anaesthetic. | 2007 Mar |
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Assessment of bacterial contamination of three multidose ophthalmic solutions. | 2007 Mar-Apr |
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Does prior instillation of a topical anaesthetic alter the pupillary mydriasis produced by tropicamide (0.5%)? | 2007 May |
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Single-stranded oligonucleotide-mediated in vivo gene repair in the rd1 retina. | 2007 May 2 |
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Phacoemulsification in vitrectomized eyes under topical anesthesia. | 2007 May-Jun |
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Phacoemulsification complication rates. | 2007 Nov |
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Toxicities of topical ophthalmic anesthetics. | 2007 Nov |
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Variation in intraocular pressure following application of tropicamide in three different dog breeds. | 2007 Nov-Dec |
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Ophthalmic examination findings in adult pygmy goats (Capra hicus). | 2007 Sep-Oct |
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Double homozygous waltzer and Ames waltzer mice provide no evidence of retinal degeneration. | 2008 |
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Different tropism of adenoviruses and adeno-associated viruses to corneal cells: implications for corneal gene therapy. | 2008 |
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Cataract surgery complication rates. | 2008 Aug |
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Protein kinase C-delta mediates neuronal apoptosis in the retinas of diabetic rats via the Akt signaling pathway. | 2008 Aug |
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Evaluation of duration of corneal anesthesia induced with ophthalmic 0.5% proparacaine hydrochloride by use of a Cochet-Bonnet aesthesiometer in clinically normal horses. | 2008 Dec |
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Adjustable suture strabismus surgery in infants and children. | 2008 Dec |
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Recombinant anti-vascular endothelial growth factor fusion protein efficiently suppresses choridal neovasularization in monkeys. | 2008 Jan 10 |
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The importance of central corneal thickness measurements and decision making in general ophthalmology clinics: a masked observational study. | 2008 Jan 20 |
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Effect of immunomodulation with anti-CD40L antibody on adenoviral-mediated transgene expression in mouse anterior segment. | 2008 Jan 9 |
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Helical computed tomographic dacryocystography and its role in the diagnosis and management of lacrimal drainage system blocks and medial canthal masses. | 2008 Jan-Feb |
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Inducible ablation of melanopsin-expressing retinal ganglion cells reveals their central role in non-image forming visual responses. | 2008 Jun 11 |
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Down-regulation of Notch signaling during corneal epithelial proliferation. | 2008 Jun 5 |
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Pulsatile ocular blood flow in healthy Koreans. | 2008 Mar |
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Ocular biodistribution of bevasiranib following a single intravitreal injection to rabbit eyes. | 2008 May 28 |
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Anterior sub-Tenon's anesthesia for the treatment of retinopathy of prematurity. | 2008 May-Jun |
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Patient comfort and surgeon satisfaction during cataract surgery using topical anesthesia with or without dexmedetomidine sedation. | 2008 May-Jun |
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Investigative modalities in infectious keratitis. | 2008 May-Jun |
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Transconjunctival penetration of mitomycin C. | 2008 May-Jun |
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Anaesthesia for ophthalmologic surgical procedures in a patient with advanced amyotrophic lateral sclerosis: a case report. | 2008 Nov 20 |
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Agreement between two Goldmann type applanation tonometers. | 2008 Nov-Dec |
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Transmission electron microscopy study of corneal epithelial flaps following removal using mechanical scraping, alcohol, and epikeratome techniques. | 2008 Sep |
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Conjunctivolimbal autograft using a fibrin adhesive in pterygium surgery. | 2008 Sep |
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A lacrimal sac abscess incision and drainage technique. | 2008 Sep |
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Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR. | 2008 Sep |
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Neuroprotective effect of intravitreal triamcinolone acetonide against photoreceptor apoptosis in a rabbit model of subretinal hemorrhage. | 2008 Sep |
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Changes in ocular aquaporin-4 (AQP4) expression following retinal injury. | 2008 Sep 25 |
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Targeted destruction of photosensitive retinal ganglion cells with a saporin conjugate alters the effects of light on mouse circadian rhythms. | 2008 Sep 5 |
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Intraoperative adjustable suture strabismus surgery under topical and subconjunctival anesthesia. | 2008 Sep-Oct |
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Liquid nitrogen cryotherapy of superior limbic keratoconjunctivitis. | 2009 Feb |
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Antibacterial activity of preservative-free topical anesthetic drops in current use in ophthalmology departments. | 2009 Jan |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/proparacaine.html
Usual Dosage: Removal of foreign bodies and sutures, and for tonometry: 1 to 2 drops (in single instillations) in each eye before operating.
Short corneal and conjunctival procedures: 1 drop in each eye every 5 to 10 minutes for 5 to 7 doses.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3198982
The effects of proparacaine on the actin cytoskeleton of corneal epithelial cells were studied in vitro. Spreading rat corneal epithelial cells in tissue culture were treated with proparacaine hydrochloride. At the lowest drug concentration used (0.01 mM), no effects were seen on the actin cytoskeleton. At 1.0 mM, some disruption of stress fibers was evident and actin was redistributed in a diffuse fashion. Above 1.0 mM, cell spreading was completely abolished and most cells detached from the substratum.
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 524.1982
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N0000175539
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N0000175976
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C245
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)