Propoxycaine
Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB09342
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
Identification
- Generic Name
- Propoxycaine
- DrugBank Accession Number
- DB09342
- Background
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
- Weight
- Average: 294.395
Monoisotopic: 294.194342705 - Chemical Formula
- C16H26N2O3
- Synonyms
- Propoxycaine
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.
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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.
Target Actions Organism AVoltage-gated sodium channel alpha subunit blockerHumans - 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.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Propoxycaine. Abiraterone The risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Propoxycaine. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Propoxycaine. Acetazolamide The risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Propoxycaine. Acetic acid The risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Propoxycaine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Propoxycaine hydrochloride K490D39G46 550-83-4 GITPCGSPKUQZTE-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)
- Affected organisms
- Not Available
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
- 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. [Article]
- 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. [Article]
- PROPOXYCAINE [Link]
- New local anesthetic solutions containing propoxycaine [Link]
- Handbook of Dental Anesthesia- Ebook [Link]
- Essentials of local anesthetic pharmacology [Link]
- Propoxycaine Hydrochloride [Link]
- External Links
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 146-151 http://www.pharmacopeia.cn/v29240/usp29nf24s0_m70480.html water solubility 10 µg/mL in water http://www.pharmacopeia.cn/v29240/usp29nf24s0_m70480.html - Predicted Properties
Property Value Source Water Solubility 1.79 mg/mL ALOGPS logP 2.89 ALOGPS logP 2.6 Chemaxon logS -2.2 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 34.2 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-002r-9310000000-0db616714a5bddfba6ae Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6w-5590000000-8a51d601fbbf817027dc Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-1930000000-68af02e55f72263c4c49 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udr-2920000000-c2c9103611c97713fa7f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0zg0-1900000000-3e7a109a353e5dee1fec Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0019-4900000000-bea34e9227a11289094c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0910000000-8980d2419710c99ba3a5 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 170.02556 predictedDeepCCS 1.0 (2019) [M+H]+ 172.38354 predictedDeepCCS 1.0 (2019) [M+Na]+ 178.4767 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Blocker
- General 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 sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient (PubMed:14672992). Plays a key role in brain, probably by regulating the moment when neurotransmitters are released in neurons. Involved in sensory perception of mechanical pain: activation in somatosensory neurons induces pain without neurogenic inflammation and produces hypersensitivity to mechanical, but not thermal stimuli
- Specific Function
- voltage-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential
Components:
References
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine (PubMed:7980644). Catalyzes the transesterification of cocaine to form cocaethylene (PubMed:7980644). Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate (PubMed:7980644). Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes of 2-arachidonoylglycerol and prostaglandins (PubMed:21049984). Hydrolyzes cellular cholesteryl esters to free cholesterols and promotes reverse cholesterol transport (RCT) by facilitating both the initial and final steps in the process (PubMed:11015575, PubMed:16024911, PubMed:16971496, PubMed:18762277). First of all, allows free cholesterol efflux from macrophages to extracellular cholesterol acceptors and secondly, releases free cholesterol from lipoprotein-delivered cholesteryl esters in the liver for bile acid synthesis or direct secretion into the bile (PubMed:16971496, PubMed:18599737, PubMed:18762277)
- Specific Function
- carboxylesterase activity
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- Handbook of Dental Anesthesia- Ebook [Link]
Drug created at November 27, 2015 20:23 / Updated at June 02, 2024 21:56