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Proparacaine

Proparacaine structure

Proparacaine 

structure
  • CAS No:

    499-67-2

  • Formula:

    C16H26N2O3

  • Chemical Name:

    Proparacaine

  • Synonyms:

    Benzoic acid,3-amino-4-propoxy-,2-(diethylamino)ethyl ester;Ophthaine;Proparacaine;Proxymetacaine;3-Amino-4-propoxybenzoic acid 2-(diethylamino)ethyl ester;2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate

  • Categories:

    Active Pharmaceutical Ingredients  >  Anesthetic Agents

Description

Crystalline Solid


Solid


Proparacaine is a benzoate ester.|Proparacaine is a topical anesthetic drug of the amino ester group. It is found in ophthalmic solutions at a concentration of 0.5% as the hydrochloride salt.|Proparacaine is a Local Anesthetic. The physiologic effect of proparacaine is by means of Local Anesthesia.|Proparacaine is a benzoic acid derivative anesthetic agent, with local anesthetic activity. Upon administration, proparacaine stabilizes the neuronal membrane by binding to and inhibiting voltage-gated sodium channels. This inhibits the sodium ion influx required for the initiation and conduction of impulses within the neuronal cell, increases the threshold for electrical stimulation and results in a loss of sensation.

Proparacaine Basic Attributes

294.395

294.39

207-884-9

B4OB0JHI1X

DTXSID30198146

C61910

S - Sensory organs

Characteristics

64.8

2.5

Solid

1.065

182-183.30C

434.4ºC at 760 mmHg

216.5ºC

1.527

H2O: soluble

Refrigerator

9.5E-08mmHg at 25°C

3.2None

3.2

Drug Information

Used as a local (ophthalmic) anesthetic.|FDA Label

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.

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)

Plasma

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.

2-(diethylamino)ethyl 3-amino-4-propoxybenzoate

Proparacaine Use and Manufacturing

Uses

Topical anesthetic (ophthalmic)

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:294.39
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:294.19434270
Monoisotopic Mass:294.19434270
Topological Polar Surface Area:64.8
Heavy Atom Count:21
Complexity:295
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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