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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
Structure of PROPARACAINE

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

HIDE SMILES / InChI
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Alcaine

Approved Use

ALCAINE® 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 Date

1953
PubMed

PubMed

TitleDatePubMed
Subtenon lidocaine vs topical proparacaine in adult strabismus surgery.
2006 Fall
Calcium-binding protein calretinin immunoreactivity in the dog superior colliculus.
2006 Oct 30
Secretory leukocyte protease inhibitor is an inducible antimicrobial peptide expressed in Staphylococcus aureus endophthalmitis.
2007
Topical anesthesia in transconjunctival sutureless 25-gauge vitrectomy for macular-based disorders.
2007
Assisted local anaesthesia for endoscopic dacryocystorhinostomy.
2007 Apr
Posterior vitrectomy under topical anesthesia.
2007 Apr
[Self-medication with local anaesthetics by glaucoma patients using teletonometry].
2007 Dec
Effect of proparacaine on central corneal thickness values: an evaluation using noncontact specular microscopy and pentacam.
2007 Jan
Topical anaesthesia alone versus topical anaesthesia with intracameral lidocaine for phacoemulsification.
2007 Jul 18
Prevalence of feline herpesvirus 1, Chlamydophila felis, and Mycoplasma spp DNA in conjunctival cells collected from cats with and without conjunctivitis.
2007 Jun
Laser photocoagulation combined with intravitreal triamcinolone acetonide injection in proliferative diabetic retinopathy with macular edema.
2007 Mar
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
Assessment of bacterial contamination of three multidose ophthalmic solutions.
2007 Mar-Apr
Does prior instillation of a topical anaesthetic alter the pupillary mydriasis produced by tropicamide (0.5%)?
2007 May
Single-stranded oligonucleotide-mediated in vivo gene repair in the rd1 retina.
2007 May 2
Phacoemulsification in vitrectomized eyes under topical anesthesia.
2007 May-Jun
Phacoemulsification complication rates.
2007 Nov
Toxicities of topical ophthalmic anesthetics.
2007 Nov
Variation in intraocular pressure following application of tropicamide in three different dog breeds.
2007 Nov-Dec
Ophthalmic examination findings in adult pygmy goats (Capra hicus).
2007 Sep-Oct
Double homozygous waltzer and Ames waltzer mice provide no evidence of retinal degeneration.
2008
Different tropism of adenoviruses and adeno-associated viruses to corneal cells: implications for corneal gene therapy.
2008
Cataract surgery complication rates.
2008 Aug
Protein kinase C-delta mediates neuronal apoptosis in the retinas of diabetic rats via the Akt signaling pathway.
2008 Aug
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
Adjustable suture strabismus surgery in infants and children.
2008 Dec
Recombinant anti-vascular endothelial growth factor fusion protein efficiently suppresses choridal neovasularization in monkeys.
2008 Jan 10
The importance of central corneal thickness measurements and decision making in general ophthalmology clinics: a masked observational study.
2008 Jan 20
Effect of immunomodulation with anti-CD40L antibody on adenoviral-mediated transgene expression in mouse anterior segment.
2008 Jan 9
Helical computed tomographic dacryocystography and its role in the diagnosis and management of lacrimal drainage system blocks and medial canthal masses.
2008 Jan-Feb
Inducible ablation of melanopsin-expressing retinal ganglion cells reveals their central role in non-image forming visual responses.
2008 Jun 11
Down-regulation of Notch signaling during corneal epithelial proliferation.
2008 Jun 5
Pulsatile ocular blood flow in healthy Koreans.
2008 Mar
Ocular biodistribution of bevasiranib following a single intravitreal injection to rabbit eyes.
2008 May 28
Anterior sub-Tenon's anesthesia for the treatment of retinopathy of prematurity.
2008 May-Jun
Patient comfort and surgeon satisfaction during cataract surgery using topical anesthesia with or without dexmedetomidine sedation.
2008 May-Jun
Investigative modalities in infectious keratitis.
2008 May-Jun
Transconjunctival penetration of mitomycin C.
2008 May-Jun
Anaesthesia for ophthalmologic surgical procedures in a patient with advanced amyotrophic lateral sclerosis: a case report.
2008 Nov 20
Agreement between two Goldmann type applanation tonometers.
2008 Nov-Dec
Transmission electron microscopy study of corneal epithelial flaps following removal using mechanical scraping, alcohol, and epikeratome techniques.
2008 Sep
Conjunctivolimbal autograft using a fibrin adhesive in pterygium surgery.
2008 Sep
A lacrimal sac abscess incision and drainage technique.
2008 Sep
Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR.
2008 Sep
Neuroprotective effect of intravitreal triamcinolone acetonide against photoreceptor apoptosis in a rabbit model of subretinal hemorrhage.
2008 Sep
Changes in ocular aquaporin-4 (AQP4) expression following retinal injury.
2008 Sep 25
Targeted destruction of photosensitive retinal ganglion cells with a saporin conjugate alters the effects of light on mouse circadian rhythms.
2008 Sep 5
Intraoperative adjustable suture strabismus surgery under topical and subconjunctival anesthesia.
2008 Sep-Oct
Liquid nitrogen cryotherapy of superior limbic keratoconjunctivitis.
2009 Feb
Antibacterial activity of preservative-free topical anesthetic drops in current use in ophthalmology departments.
2009 Jan
Patents

Sample Use Guides

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
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.
Name Type Language
PROPARACAINE
MI   VANDF  
Common Name English
PROPARACAINE [VANDF]
Common Name English
proxymetacaine [INN]
Common Name English
Proxymetacaine [WHO-DD]
Common Name English
2-(DIETHYLAMINO)ETHYL 3-AMINO-4-PROPOXYBENZOATE
Systematic Name English
PROXYMETACAINE
INN   WHO-DD  
INN  
Official Name English
BENZOIC ACID, 3-AMINO-4-PROPOXY-, 2-(DIETHYLAMINO)ETHYL ESTER
Common Name English
PROPARACAINE [MI]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 524.1982
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NDF-RT N0000175539
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NDF-RT N0000175976
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WHO-VATC QS01HA04
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WHO-ATC S01HA04
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NCI_THESAURUS C245
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Code System Code Type Description
CAS
499-67-2
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PRIMARY
NCI_THESAURUS
C61910
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PRIMARY
INN
540
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PRIMARY
RXCUI
34905
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PRIMARY RxNorm
SMS_ID
100000080841
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PRIMARY
EVMPD
SUB10152MIG
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PUBCHEM
4935
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WIKIPEDIA
PROXYMETACAINE
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PRIMARY
MERCK INDEX
m9191
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PRIMARY Merck Index
DAILYMED
B4OB0JHI1X
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PRIMARY
DRUG BANK
DB00807
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PRIMARY
ECHA (EC/EINECS)
207-884-9
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PRIMARY
IUPHAR
7283
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PRIMARY
MESH
C005717
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PRIMARY
ChEMBL
CHEMBL1196
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PRIMARY
FDA UNII
B4OB0JHI1X
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PRIMARY
EPA CompTox
DTXSID30198146
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PRIMARY
DRUG CENTRAL
2294
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PRIMARY