Identification

Name
Oxetacaine
Accession Number
DB12532
Description

Oxetacaine, also called oxethazaince, is a potent surface analgesic with the molecular formula N, N-bis-(N-methyl-N-phenyl-t-butyl-acetamide)-beta-hydroxyethylamine that conserves its unionized form at low pH levels. Its actions have shown to relieve dysphagia, relieve pain due to reflux, chronic gastritis, and duodenal ulcer.1 Oxetacaine is approved by Health Canada since 1995 for its use as an antacid combination in over-the-counter preparations.6 It is also in the list of approved derivatives of herbal products by the EMA.7

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 467.654
Monoisotopic: 467.314792192
Chemical Formula
C28H41N3O3
Synonyms
  • Oxetacaine
External IDs
  • WY-806

Pharmacology

Indication

Oxetacaine is available as an over-the-counter antacid and it is used to alleviate pain associated with gastritis, peptic ulcer disease, heartburn, esophagitis, hiatus hernia, and anorexia.3

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Oxetacaine improves common gastrointestinal symptoms.3 Oxetacaine is part of the anesthetic antacids which increase the gastric pH while providing relief from pain for a longer period of duration at a lower dosage. This property has been reported to relieve the symptoms of hyperacidity. Oxetacaine is reported to produce a reversible loss of sensation and to provide a prompt and prolonged relief of pain. In vitro, oxetacaine was showed to produce an antispasmodic action on the smooth muscle and block the action of serotonin.4

The local efficacy of oxetacaine has been proven to be 2000 times more potent than lignocaine and 500 times more potent than cocaine. Its anesthetic action produces the loss of sensation which can be explained by its inhibitory activity against the nerve impulses and de decrease in permeability of the cell membrane.4

Mechanism of action

Oxetacaine inhibits gastric acid secretion by suppressing gastrin secretion.3

Moreover, oxetacaine exerts a local anesthetic effect on the gastric mucosa. This potent local anesthetic effect of oxetacaine may be explained by its unique chemical characteristics in which, as a weak base, it is relatively non-ionized in acidic solutions whereas its hydrochloride salt is soluble in organic solvents and it can penetrate cell membranes.2 Oxetacaine diminishes the conduction of sensory nerve impulses near the application site which in order reduces the permeability of the cell membrane to sodium ions.4 This activity is performed by the incorporation of the unionized form into the cell membrane.5

TargetActionsOrganism
AGastrin
inhibition of synthesis
Humans
Absorption

A peak plasma concentration of oxetacaine of approximately 20 ng/ml is attained about one hour after oral administration.4 LEss than 1/3 of the administered dose is absorbed as it undergoes extensive metabolism.5

Volume of distribution

This pharmacokinetic property has not been studied.

Protein binding

Due to the low half-life, it is thought that oxetacaine, when absorbed, presents a very low protein plasma binding.5

Metabolism

Oxetacaine is rapidly and extensively metabolized hepatically. After metabolism, there is a formation of primary metabolites such as beta-hydroxy-mephentermine and beta-hydroxy-phentermine. The major metabolites are found in the plasma in insignificant amounts.4

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Route of elimination

Less than 0.1% of the amdinistered dose is recovered in urine within 24 hours in the form of unchanged oxetacaine or its metabolites.4

Half-life

Oxetacaine presents a very short half-life of approximately one hour.4

Clearance

This pharmacokinetic property has not been studied.

Adverse Effects
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Toxicity

When orally administered, oxetacaine presents a good tolerance. However, following intravenous injection, oxetacaine toxicity is high and it is presented as a depression in myocardial contractility and impaired conduction.2

Affected organisms
  • Humans and other mammals
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
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Oxetacaine.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Oxetacaine.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Oxetacaine.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Oxetacaine.
AlectinibThe metabolism of Alectinib can be decreased when combined with Oxetacaine.
AlfuzosinThe metabolism of Alfuzosin can be decreased when combined with Oxetacaine.
AlpelisibThe metabolism of Alpelisib can be decreased when combined with Oxetacaine.
AlprazolamThe metabolism of Alprazolam can be decreased when combined with Oxetacaine.
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Oxetacaine.
AmiodaroneThe metabolism of Amiodarone can be decreased when combined with Oxetacaine.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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

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

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

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Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Mucaine - SusOxetacaine (10 mg) + Aluminum hydroxide (300 mg) + Magnesium hydroxide (100 mg)SuspensionOralAurium Pharma Inc1995-12-312018-06-14Canada flag

Categories

ATC Codes
C05AD06 — Oxetacaine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Alpha amino acids and derivatives / Phenylpropanes / Tertiary carboxylic acid amides / Trialkylamines / 1,2-aminoalcohols / Primary alcohols / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1,2-aminoalcohol / Alcohol / Alkanolamine / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Amphetamine or derivatives / Aromatic homomonocyclic compound / Carbonyl group / Carboxamide group
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
amino acid amide (CHEBI:31947)

Chemical Identifiers

UNII
IP8QT76V17
CAS number
126-27-2
InChI Key
FTLDJPRFCGDUFH-UHFFFAOYSA-N
InChI
InChI=1S/C28H41N3O3/c1-27(2,19-23-13-9-7-10-14-23)29(5)25(33)21-31(17-18-32)22-26(34)30(6)28(3,4)20-24-15-11-8-12-16-24/h7-16,32H,17-22H2,1-6H3
IUPAC Name
2-[(2-hydroxyethyl)({[methyl(2-methyl-1-phenylpropan-2-yl)carbamoyl]methyl})amino]-N-methyl-N-(2-methyl-1-phenylpropan-2-yl)acetamide
SMILES
CN(C(=O)CN(CCO)CC(=O)N(C)C(C)(C)CC1=CC=CC=C1)C(C)(C)CC1=CC=CC=C1

References

General References
  1. BALMFORTH GV, SAMUEL RK: CONTROLLED TRIAL OF OXETHAZAINE AS AN ANALGESIC IN DUODENAL ULCER. Br Med J. 1964 Feb 8;1(5379):355-6. [PubMed:14079039]
  2. Masuda Y, Yoshizawa T, Ozaki M, Tanaka T: The metabolic and hemodynamic effects of oxethazaine in the perfused rat liver. Jpn J Pharmacol. 1996 Mar;70(3):243-52. [PubMed:8935718]
  3. Namba H, Nishimura Y, Kurata N, Iwase M, Hirai T, Kiuchi Y: Inhibitory Effect of Oxethazaine on Midazolam Metabolism in Rats. Biol Pharm Bull. 2017;40(9):1361-1365. doi: 10.1248/bpb.b16-01016. [PubMed:28867721]
  4. Parakh R. and Patil N. (2017). International Journal of Research in Medical Sciences. MSJ Online.
  5. Kapoor A. and Raju S. (2013). Ilustrated Medical Pharmacology. Jaypee Brothers. [ISBN:978-93-5090-655-2]
  6. Health Canada [Link]
  7. EMA Herbal substances [Link]
KEGG Compound
C12552
PubChem Compound
4621
PubChem Substance
347828759
ChemSpider
4460
BindingDB
50017672
ChEBI
31947
ChEMBL
CHEMBL127592
ZINC
ZINC000003874585
Wikipedia
Oxetacaine
MSDS
Download (276 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentRadiation-induced Oesophagitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SuspensionOral
SuspensionOral10 mg/5ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)100-101 ºC'MSDS'
boiling point (°C)630 ºC at 760 mm Hg'MSDS'
water solubility<0.1 g/100 ml at 23 ºC'MSDS'
pKa6.25Posey E., Boler K. and Posey L. The Amerian Journal of Digestive Diseases. (1969)
Predicted Properties
PropertyValueSource
Water Solubility0.0102 mg/mLALOGPS
logP3.67ALOGPS
logP3.16ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)5.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.09 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity138.53 m3·mol-1ChemAxon
Polarizability52.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-4921100000-a1f5b0f2bfd88a9426a7

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibition of synthesis
General Function
Gastrin stimulates the stomach mucosa to produce and secrete hydrochloric acid and the pancreas to secrete its digestive enzymes. It also stimulates smooth muscle contraction and increases blood circulation and water secretion in the stomach and intestine.
Specific Function
Hormone activity
Gene Name
GAST
Uniprot ID
P01350
Uniprot Name
Gastrin
Molecular Weight
11393.63 Da
References
  1. Namba H, Nishimura Y, Kurata N, Iwase M, Hirai T, Kiuchi Y: Inhibitory Effect of Oxethazaine on Midazolam Metabolism in Rats. Biol Pharm Bull. 2017;40(9):1361-1365. doi: 10.1248/bpb.b16-01016. [PubMed:28867721]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Parakh R. and Patil N. (2017). International Journal of Research in Medical Sciences. MSJ Online.

Drug created on October 20, 2016 16:45 / Updated on June 12, 2020 10:53

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