SynCED: Proparacaine

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:41 UTC

Update Date

2026-05-14 16:49:29 UTC

Accession Number

CHEM002276

Identification

Common Name

Proparacaine

Class

Small Molecule

Description

Proparacaine is only found in individuals that have used or taken this drug. It 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%. [Wikipedia]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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Anesthetic, Local
Drug
Ester
Ether
Lachrymator
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Proxymetacaine	Kegg
Prossimetacaina	HMDB
Proximetacainum	HMDB
Ophthetic	HMDB
Parcaine	HMDB
Alcaine	HMDB
Ocu-caine	HMDB
Proxymetacaine hydrochloride	HMDB
AK-taine	HMDB
Kainair	HMDB
Proxymethacaine	HMDB
Chibro-kerakain	HMDB
Kéracaine	HMDB
Minims proxymetacaine hydrochloride	HMDB
Ophthaine	HMDB
Proparakain-pos	HMDB
Proxymetacaine monohydrochloride	HMDB
Proparacaine hydrochloride	HMDB
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate	HMDB
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester	HMDB
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate monohydrochloride	HMDB
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochloride*benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochloride	HMDB
Proparacaine HCL	HMDB

Chemical Formula

C₁₆H₂₆N₂O₃

Average Molecular Mass

294.389 g/mol

Monoisotopic Mass

294.194 g/mol

CAS Registry Number

499-67-2

IUPAC Name

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

Traditional Name

proparacaine

SMILES

CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC

InChI Identifier

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

InChI Key

KCLANYCVBBTKTO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Aminophenyl ether
Phenoxy compound
Benzoyl
Aniline or substituted anilines
Phenol ether
Alkyl aryl ether
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:8485 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Proparacaine Pathway	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	182-183.3°C
Boiling Point	Not Available
Solubility	1.39e+00 g/L

Predicted Properties

Property	Value	Source
Water Solubility	1.39 g/L	ALOGPS
logP	2.97	ALOGPS
logP	2.6	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.79 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	86.04 m³·mol⁻¹	ChemAxon
Polarizability	34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Topical (eye drop).

Mechanism of Toxicity

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

Plasma

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used as an ophthalmic anesthetic (as eye drops) to reduce pain and discomfort during procedures involving the eye. [Wikipedia]

Minimum Risk Level

Not Available

Health Effects

Not Available

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. (1)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00807

HMDB ID

HMDB0014945

FooDB ID

Not Available

Phenol Explorer ID