Identification
- Summary
Oxetacaine is an antacid used to treat gastritis, peptic ulcer disease, heartburn, esophagitis, hiatus hernia, and anorexia.
- Generic Name
- Oxetacaine
- DrugBank Accession Number
- DB12532
- Background
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
Structure for Oxetacaine (DB12532)
- 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
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Acid reflux Combination Product in combination with: Magnesium hydroxide (DB09104), Aluminum hydroxide (DB06723) ••• ••• Symptomatic treatment of Anal fissures ••• ••• ••••• Symptomatic treatment of Hemorrhoids ••• ••• ••••• Symptomatic treatment of Proctitis ••• ••• ••••• Symptomatic treatment of Pruritus ani ••• ••• ••••• - Contraindications & Blackbox Warnings
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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
Target Actions Organism AGastrin inhibition of synthesisHumans - 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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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
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Oxetacaine. Abiraterone The risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Oxetacaine. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Oxetacaine. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Oxetacaine. Acetazolamide The risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Oxetacaine. - Food Interactions
- No interactions found.
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.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Mucaine - Sus Oxetacaine (10 mg / 5 mL) + Aluminum hydroxide (300 mg / 5 mL) + Magnesium hydroxide (100 mg / 5 mL) Suspension Oral Aurium Pharma Inc 1995-12-31 2018-06-14 Canada 
MUCAINE 200 ML SUSPANSIYON Oxetacaine (10 mg/5ml) + Aluminum hydroxide (291 mg/5ml) + Magnesium hydroxide (98 mg/5ml) Suspension Oral TURGUT İLAÇLARI A.Ş. 2006-11-02 Not applicable Turkey 
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)
- Affected organisms
- Humans and other mammals
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
- BALMFORTH GV, SAMUEL RK: CONTROLLED TRIAL OF OXETHAZAINE AS AN ANALGESIC IN DUODENAL ULCER. Br Med J. 1964 Feb 8;1(5379):355-6. [Article]
- 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. [Article]
- 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. [Article]
- Parakh R. and Patil N. (2017). International Journal of Research in Medical Sciences. MSJ Online.
- Kapoor A. and Raju S. (2013). Ilustrated Medical Pharmacology. Jaypee Brothers. [ISBN:978-93-5090-655-2]
- Health Canada [Link]
- EMA Herbal substances [Link]
- External Links
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Terminated Treatment Radiation-induced Oesophagitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 0.25 % Suspension Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source 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' pKa 6.25 Posey E., Boler K. and Posey L. The Amerian Journal of Digestive Diseases. (1969) - Predicted Properties
Property Value Source Water Solubility 0.0102 mg/mL ALOGPS logP 3.67 ALOGPS logP 3.16 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 15.59 Chemaxon pKa (Strongest Basic) 5.78 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 64.09 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 138.53 m3·mol-1 Chemaxon Polarizability 52.95 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 220.5000638 predictedDarkChem Lite v0.1.0 [M-H]- 207.58183 predictedDeepCCS 1.0 (2019) [M+H]+ 221.2159638 predictedDarkChem Lite v0.1.0 [M+H]+ 209.93983 predictedDeepCCS 1.0 (2019) [M+Na]+ 220.5704638 predictedDarkChem Lite v0.1.0 [M+Na]+ 216.03297 predictedDeepCCS 1.0 (2019)
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
- 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. [Article]
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
- Parakh R. and Patil N. (2017). International Journal of Research in Medical Sciences. MSJ Online.
Drug created at October 20, 2016 22:45 / Updated at May 27, 2021 02:58