Proparacaine hydrochloride Chemical Properties

Melting point:

182.0-183.3°

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol, Water

form 

Solid

pka

3.2(at 25℃)

color 

White to Off-White

λmax

300nm(MeOH)(lit.)

Merck 

14,7807

InChI

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

InChIKey

BFUUJUGQJUTPAF-UHFFFAOYSA-N

SMILES

C(OCCN(CC)CC)(=O)C1=CC=C(OCCC)C(N)=C1.[H]Cl

CAS DataBase Reference

5875-06-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36-43

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DG3065000

HS Code 

2922504500

MSDS

• Language:English Provider:SigmaAldrich

Proparacaine hydrochloride Usage And Synthesis

Description

Proparacaine Hydrochloride is the hydrochloride salt form of proparacaine, a benzoic acid derivative with local anesthetic property. Proparacaine hydrochloride stabilizes the neuronal membrane by binding to and inhibiting voltage-gated sodium channels, thereby inhibiting sodium ion influx required for the initiation and conduction of impulses within the neuronal cell, and resulting in a loss of sensation.

Uses

Topical anesthetic (ophthalmic); Neuronal conductance inhibitor.

brand name

Alcaine (Alcon); Ophthetic (Allergan); Paracaine (Optopics).

Clinical Use

Proparacaine Hydrochloride Ophthalmic Solution is indicated for topical anesthesia in ophthalmic practice.

Side effects

Occasional temporary stinging, burning and conjunctival redness may occur with the use of proparacaine. A rare, severe, immediate-type, apparently hyperallergic corneal reaction characterized by acute, intense and diffuse epithelial keratitis, a gray, ground glass appearance, sloughing of large areas of necrotic epithelium, corneal filaments and sometimes iritis with descemetitis has been reported. Allergic contact dermatitis from proparacaine with drying and fissuring of the fingertips has been reported.

Mode of action

The mechanism of action of proparacaine hydrochloride is to reduce the instantaneous permeability of neurons to sodium, stabilize the nerve cell membrane, and prevent the generation and conduction of nerve electrical impulses, thereby producing anesthesia.Likely inhibits epithelial voltage gated sodium channels like other local anesthetics.

References

1. Identification, synthesis and structural confirmation of process-related impurities in proparacaine hydrochloride. DOI:10.1016/j.jpba.2020.113497
2. https://pi.bausch.com/globalassets/pdf/PackageInserts/Pharma/Rx-Generics/Proparacaine-HCl-Ophthalmic-Solution.pdf
3. Imming P., Sinning C., Meyer A. Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct; 5(10):821-34. DOI:10.1038/nrd2132
4. T., Levent T., Inci M.A. Toxic keratopathy associated with abuse of topical anesthetics and amniotic membrane transplantation for treatment. Int J Ophthalmol. 2015; 8(5): 938–944. DOI:10.3980/j.issn.2222-3959.2015.05.15
5. Proparacaine Hydrochloride Topical Drop and Intracameral 0.5% Lignocaine for Phacotrabeculectomy in Patients with Primary Open Angle Glaucoma DOI:10.4103/0974-9233.134669
6. https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=447a2a64-0507-4fe8-bb44-cc36c3916151&type=display

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