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Details

Stereochemistry ACHIRAL
Molecular Formula C16H26N2O3
Molecular Weight 294.3892
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPARACAINE

SMILES

CCCOC1=CC=C(C=C1N)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

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%. 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.

Originator

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
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
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
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
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
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
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

In Vivo Use Guide
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
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
NDF-RT N0000175539
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
NDF-RT N0000175976
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
WHO-VATC QS01HA04
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
WHO-ATC S01HA04
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
Code System Code Type Description
CAS
499-67-2
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
NCI_THESAURUS
C61910
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
INN
540
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
RXCUI
34905
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY RxNorm
EVMPD
SUB10152MIG
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
PUBCHEM
4935
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY SWITZERF
WIKIPEDIA
PROXYMETACAINE
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
MERCK INDEX
M9191
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY Merck Index
DRUG BANK
DB00807
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
ECHA (EC/EINECS)
207-884-9
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
IUPHAR
7283
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
MESH
C005717
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
ChEMBL
CHEMBL1196
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY
EPA CompTox
499-67-2
Created by admin on Tue Mar 06 12:33:48 UTC 2018 , Edited by admin on Tue Mar 06 12:33:48 UTC 2018
PRIMARY