Identification

Name
Propoxycaine
Accession Number
DB09342
Description

Propoxycaine is a local anesthetic of the ester type that has a rapid onset of action and a longer duration of action than procaine hydrochloride 3. This drug was removed from the US market in 1996. Although no longer available in the United States, this medication was used in combination with procaine to aid in anesthesia during dental procedures 5. Used in combination with procaine, it was the only dental local anesthetic available in cartridge form 5.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 294.395
Monoisotopic: 294.194342705
Chemical Formula
C16H26N2O3
Synonyms
Not Available

Pharmacology

Indication

Propoxycaine is a local anesthetic medication. It was used beginning in the 1950s during dental procedures 4. It has been combined with procaine to accelerate its onset of action and provide longer-lasting anesthetic effect 5.

It was produced for use when amide local anesthetics were contraindicated due to allergy or when several amide anesthetics were unsuccessful 5.

Contraindications & Blackbox Warnings
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Pharmacodynamics

Propoxycaine is a local anesthetic which acts to decrease nerve impulses and therefore pain sensation during dental procedures 4,5,6.

Mechanism of action

Propoxycaine is a para-aminobenzoic acid ester with local anesthetic activity. Propoxycaine binds to and blocks voltage-gated sodium channels, thereby inhibiting the ionic flux essential for the conduction of nerve impulses. This results in a loss of sensation 3.

In one study, propoxycaine hydrochloride increased annular lipid fluidity in cell lipid bilayers and had a greater fluidizing effect on the inner monolayer than that of the outer monolayer 2. This may further confirm its role in modulating neural impulses.

TargetActionsOrganism
AVoltage-gated sodium channel alpha subunit
blocker
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

This drug his hydrolyzed in both the plasma and the liver by plasma esterases 6.

Route of elimination

Renal 5

Half-life
Not Available
Clearance

Via the kidneys, primarily hydrolyzed 5.

Adverse Effects
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Toxicity

The toxicity of this medication (7-8 times higher than that of procaine), has prevented this medication from being used on its own 5.

Ester-type local anesthetics are much more likely to cause an allergic reaction compared to the amide-group local anesthetics because of the formation of PABA (Para-aminobenzoic acid) during the metabolic process. PABA may cause allergic reactions that range from urticaria to anaphylaxis. PABA is also formed during the metabolism of methylparaben (a common preservative) that is normally found in multi-dose vials including lidocaine (MDV) (amide-type local anesthetic) 5,6.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Technetium Tc-99m tilmanoceptPropoxycaine may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

Product Ingredients
IngredientUNIICASInChI Key
Propoxycaine hydrochlorideK490D39G46550-83-4GITPCGSPKUQZTE-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Aminobenzoic acids and derivatives / Aminophenyl ethers / Phenoxy compounds / Benzoyl derivatives / Aniline and substituted anilines / Alkyl aryl ethers / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives
show 4 more
Substituents
Alkyl aryl ether / Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aminophenyl ether / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carboxylic acid derivative
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzoate ester (CHEBI:8496)

Chemical Identifiers

UNII
EPD1EH7F53
CAS number
86-43-1
InChI Key
CAJIGINSTLKQMM-UHFFFAOYSA-N
InChI
InChI=1S/C16H26N2O3/c1-4-10-20-15-12-13(17)7-8-14(15)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
IUPAC Name
2-(diethylamino)ethyl 4-amino-2-propoxybenzoate
SMILES
CCCOC1=CC(N)=CC=C1C(=O)OCCN(CC)CC

References

General References
  1. Hung CH, Liu KS, Shao DZ, Cheng KI, Chen YC, Chen YW: The systemic toxicity of equipotent proxymetacaine, oxybuprocaine, and bupivacaine during continuous intravenous infusion in rats. Anesth Analg. 2010 Jan 1;110(1):238-42. doi: 10.1213/ANE.0b013e3181bf6acf. Epub 2009 Nov 6. [PubMed:19897799]
  2. Lee JH, Kim DI, Mun H, Lee SK, Park JS, Kim JH, Lee JH, Park YH, Jeon YC, Yoon UC, Bae MK, Jang HO, Wood WG, Yun I: The effect of propoxycaine.HCl on the physical properties of neuronal membranes. Chem Phys Lipids. 2008 Jul;154(1):19-25. doi: 10.1016/j.chemphyslip.2008.03.009. Epub 2008 Mar 22. [PubMed:18407836]
  3. PROPOXYCAINE [Link]
  4. New local anesthetic solutions containing propoxycaine [Link]
  5. Handbook of Dental Anesthesia- Ebook [Link]
  6. Essentials of local anesthetic pharmacology [Link]
  7. Propoxycaine Hydrochloride [Link]
KEGG Compound
C07895
PubChem Compound
6843
PubChem Substance
310265217
ChemSpider
6582
BindingDB
50225492
ChEBI
8496
ChEMBL
CHEMBL1195
ZINC
ZINC000001530942
Wikipedia
Propoxycaine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)146-151http://www.pharmacopeia.cn/v29240/usp29nf24s0_m70480.html
water solubility10 µg/mL in waterhttp://www.pharmacopeia.cn/v29240/usp29nf24s0_m70480.html
Predicted Properties
PropertyValueSource
Water Solubility1.79 mg/mLALOGPS
logP2.89ALOGPS
logP2.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.79 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity86.04 m3·mol-1ChemAxon
Polarizability34.2 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Blocker
General Function
Voltage-gated sodium channel activity
Specific Function
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...

Components:
References
  1. Fozzard HA, Sheets MF, Hanck DA: The sodium channel as a target for local anesthetic drugs. Front Pharmacol. 2011 Nov 1;2:68. doi: 10.3389/fphar.2011.00068. eCollection 2011. [PubMed:22053156]
  2. PROPOXYCAINE [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Handbook of Dental Anesthesia- Ebook [Link]

Drug created on November 27, 2015 13:23 / Updated on June 12, 2020 10:52

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