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Details

Stereochemistry ACHIRAL
Molecular Formula C16H26N2O3.ClH
Molecular Weight 330.85
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPARACAINE HYDROCHLORIDE

SMILES

Cl.CCCOC1=CC=C(C=C1N)C(=O)OCCN(CC)CC

InChI

InChIKey=BFUUJUGQJUTPAF-UHFFFAOYSA-N
InChI=1S/C16H26N2O3.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula C16H26N2O3
Molecular Weight 294.3892
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Liquid nitrogen cryotherapy of superior limbic keratoconjunctivitis.
2009-02
Antibacterial activity of preservative-free topical anesthetic drops in current use in ophthalmology departments.
2009-01
Evaluation of duration of corneal anesthesia induced with ophthalmic 0.5% proparacaine hydrochloride by use of a Cochet-Bonnet aesthesiometer in clinically normal horses.
2008-12
Adjustable suture strabismus surgery in infants and children.
2008-12
Anaesthesia for ophthalmologic surgical procedures in a patient with advanced amyotrophic lateral sclerosis: a case report.
2008-11-20
Agreement between two Goldmann type applanation tonometers.
2008-11-01
Intraoperative adjustable suture strabismus surgery under topical and subconjunctival anesthesia.
2008-10-04
Changes in ocular aquaporin-4 (AQP4) expression following retinal injury.
2008-09-25
Targeted destruction of photosensitive retinal ganglion cells with a saporin conjugate alters the effects of light on mouse circadian rhythms.
2008-09-05
Transmission electron microscopy study of corneal epithelial flaps following removal using mechanical scraping, alcohol, and epikeratome techniques.
2008-09
Conjunctivolimbal autograft using a fibrin adhesive in pterygium surgery.
2008-09
A lacrimal sac abscess incision and drainage technique.
2008-09
Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR.
2008-09
Neuroprotective effect of intravitreal triamcinolone acetonide against photoreceptor apoptosis in a rabbit model of subretinal hemorrhage.
2008-09
Cataract surgery complication rates.
2008-08
Protein kinase C-delta mediates neuronal apoptosis in the retinas of diabetic rats via the Akt signaling pathway.
2008-08
Inducible ablation of melanopsin-expressing retinal ganglion cells reveals their central role in non-image forming visual responses.
2008-06-11
Anterior sub-Tenon's anesthesia for the treatment of retinopathy of prematurity.
2008-06-06
Down-regulation of Notch signaling during corneal epithelial proliferation.
2008-06-05
Ocular biodistribution of bevasiranib following a single intravitreal injection to rabbit eyes.
2008-05-28
Patient comfort and surgeon satisfaction during cataract surgery using topical anesthesia with or without dexmedetomidine sedation.
2008-05-10
Investigative modalities in infectious keratitis.
2008-04-18
Transconjunctival penetration of mitomycin C.
2008-04-18
Pulsatile ocular blood flow in healthy Koreans.
2008-03
The importance of central corneal thickness measurements and decision making in general ophthalmology clinics: a masked observational study.
2008-01-20
Recombinant anti-vascular endothelial growth factor fusion protein efficiently suppresses choridal neovasularization in monkeys.
2008-01-10
Effect of immunomodulation with anti-CD40L antibody on adenoviral-mediated transgene expression in mouse anterior segment.
2008-01-09
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
Helical computed tomographic dacryocystography and its role in the diagnosis and management of lacrimal drainage system blocks and medial canthal masses.
2007-12-26
[Self-medication with local anaesthetics by glaucoma patients using teletonometry].
2007-12
Variation in intraocular pressure following application of tropicamide in three different dog breeds.
2007-11-29
Phacoemulsification complication rates.
2007-11
Toxicities of topical ophthalmic anesthetics.
2007-11
Ophthalmic examination findings in adult pygmy goats (Capra hicus).
2007-09-01
Topical anaesthesia alone versus topical anaesthesia with intracameral lidocaine for phacoemulsification.
2007-07-18
Prevalence of feline herpesvirus 1, Chlamydophila felis, and Mycoplasma spp DNA in conjunctival cells collected from cats with and without conjunctivitis.
2007-06
Phacoemulsification in vitrectomized eyes under topical anesthesia.
2007-05-31
Single-stranded oligonucleotide-mediated in vivo gene repair in the rd1 retina.
2007-05-02
Does prior instillation of a topical anaesthetic alter the pupillary mydriasis produced by tropicamide (0.5%)?
2007-05
Assisted local anaesthesia for endoscopic dacryocystorhinostomy.
2007-04
Posterior vitrectomy under topical anesthesia.
2007-04
Laser photocoagulation combined with intravitreal triamcinolone acetonide injection in proliferative diabetic retinopathy with macular edema.
2007-03
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.
2007-03
Assessment of bacterial contamination of three multidose ophthalmic solutions.
2007-02-28
Effect of proparacaine on central corneal thickness values: an evaluation using noncontact specular microscopy and pentacam.
2007-01
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
Calcium-binding protein calretinin immunoreactivity in the dog superior colliculus.
2006-10-30
Subtenon lidocaine vs topical proparacaine in adult strabismus surgery.
2006
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:36 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:36 GMT 2025
Record UNII
U96OL57GOY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROXYMETACAINE HYDROCHLORIDE
MART.   WHO-DD  
Preferred Name English
PROPARACAINE HYDROCHLORIDE
GREEN BOOK   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
PROPARACAINE HYDROCHLORIDE [VANDF]
Common Name English
Proxymetacaine hydrochloride [WHO-DD]
Common Name English
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate monohydrochloride
Systematic Name English
PROPARACAINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
NSC-759896
Code English
PROPARACAINE HYDROCHLORIDE [MI]
Common Name English
PROPARACAINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PROXYMETACAINE HYDROCHLORIDE [MART.]
Common Name English
OPHTHETIC
Brand Name English
BENZOIC ACID, 3-AMINO-4-PROPOXY-, 2-(DIETHYLAMINO)ETHYL ESTER, MONOHYDROCHLORIDE
Common Name English
ALCAINE
Brand Name English
PROPARACAINE HCL
Common Name English
PROPARACAINE HYDROCHLORIDE [USP-RS]
Common Name English
PROPARACAINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
PARACAINE
Brand Name English
KAINAIR
Brand Name English
OPHTHAINE
Brand Name English
AK-TAINE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID0049022
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
MERCK INDEX
m9191
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY Merck Index
RXCUI
227778
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY RxNorm
PUBCHEM
22169
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
NSC
759896
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
CAS
5875-06-9
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
ChEMBL
CHEMBL1196
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
FDA UNII
U96OL57GOY
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
ECHA (EC/EINECS)
227-541-7
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
NCI_THESAURUS
C47693
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
SMS_ID
100000092580
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
RS_ITEM_NUM
1571001
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
DRUG BANK
DBSALT000459
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
DAILYMED
U96OL57GOY
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
EVMPD
SUB04118MIG
Created by admin on Mon Mar 31 17:34:36 GMT 2025 , Edited by admin on Mon Mar 31 17:34:36 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY