Basic information
- CAS
499-67-2- Standard SMILES
CCCOc1ccc(C(=O)OCCN(CC)CC)cc1N- InChIKey
KCLANYCVBBTKTO-UHFFFAOYSA-N- Molecular formula
- C16H26N2O3
- Average molar mass
- 294.39 g/mol
- Monoisotopic mass
- 294.1943427
Overview
Proparacaine is a benzoate ester.
Names & identifiers
- Preferred name
- Proparacaine
- IUPAC
- 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
- English name
- proxymetacaine
- Molecular formula
- C16H26N2O3
- Molecular weight
- 294.39
Names & synonyms
proparacaineProxymetacaine499-67-22-(Diethylamino)ethyl 3-amino-4-propoxybenzoateProximetacainumProximetacainaProssimetacainaProxymetacainum3-Amino-4-propoxybenzoic acid 2-(diethylamino)ethyl esterBENZOIC ACID, 3-AMINO-4-PROPOXY-, 2-(DIETHYLAMINO)ETHYL ESTERB4OB0JHI1XDTXSID30198146
Show more names
C07383FlucaineFluoracaineChibro-keracaineProxymetacaineHclProxymethacaineHClproxymetacaine USP/EP/BPProxymethacainehydrochloride
proxymethacaineRefChem:58606DTXCID60120637S01HA04207-884-9OphthaineProssimetacaina [DCIT]Proxymetacainum [INN-Latin]
Database identifiers
- CAS
499-67-2- PubChem CID
- 4935
- DTXSID
DTXSID30198146- ChEMBL
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 64.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 10
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 295
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.5
Solubility
Soluble
1.39e+00 g/L
Human DrugsPharmaceuticals
Melting Point
182-183.3 °C
182 - 183.3 °C
Physical DescriptionSolid
Dissociation Constants3.2
Physicochemical properties
- Melting point
- 182 · 182-183.30C
- Boiling point
- 434.4 · 434.4±35.0 °C(Predicted)
- Density
- 1.065 · 1.065
- storage temp.
- Refrigerator
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Exposure RoutesTopical (eye drop).
Toxicity Summary
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.
Signs and Symptoms
Dizziness or drowsiness; increased sweating; irregular heartbeat; muscle twitching or trembling; nausea or vomiting; shortness of breath or troubled breathing; unusual excitement, nervousness, or restlessness; unusual tiredness or weakness. Burning, stinging, redness, or other irritation of eye. (L1482)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
ATC Code
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
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.
Mechanism of Action
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.
Metabolism/Metabolites
Plasma
Plasma
FDA Pharmacological Classification
B4OB0JHI1X
PROPARACAINE
Physiologic Effects [PE] - Local Anesthesia
Established Pharmacologic Class [EPC] - Local Anesthetic
Proparacaine is a Local Anesthetic. The physiologic effect of proparacaine is by means of Local Anesthesia.
MeSH Pharmacological Classification
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.
Cellular Locations
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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