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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

Molecular Formula C16H26N2O3
Molecular Weight 294.3892
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Primary TargetPharmacologyConditionPotency
1.9 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Alcaine

PubMed

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.
Substance Class Chemical
Record UNII
B4OB0JHI1X
Record Status Validated (UNII)
Record Version