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Identification
- Summary
Amylocaine is a local and topical anaesthetic agent.
- Generic Name
- Amylocaine
- DrugBank Accession Number
- DB09088
- Background
Despite the introduction of using cocaine injections for regional anesthesia in 1884, non-addictive substitutes were sought after immediately 4. Finally, in 1903 the world's first synthetic and non-addictive local anesthetic, amylocaine, was synthesized and patented under the name Forneaucaine by Ernest Fourneau at the Pasteur Institute 4. Elsewhere in English speaking countries it was referred to as Stovaine, given the meaning of the French word 'fourneau' as 'stove' in English 4.
Although amylocaine could be administered topically or injected, it was most widely used for spinal anesthesia 4. Even though it certainly possessed less severe side effects than cocaine 4, the eventual development and clinical use of newer, more effective, and even safer local anesthetics like lidocaine, bupivicaine, and prilocaine in the 1940s and 1950s superseded and made the use of amylocaine obsolete.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Amylocaine (DB09088)
- Weight
- Average: 235.327
Monoisotopic: 235.15722892 - Chemical Formula
- C14H21NO2
- Synonyms
- 1-(Dimethylamino)-2-methyl-2-butanol benzoate
- Amyléine
- Amylocaine
- Stovaine
Pharmacology
- Indication
The most common indication for the usage of amylocaine was spinal anesthesia 1.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Pharyngitis Combination Product in combination with: Bacitracin (DB00626), Neomycin (DB00994) •••••••••••• ••••••• Used in combination to treat Sore throat Combination Product in combination with: Neomycin (DB00994), Bacitracin (DB00626) •••••••••••• ••••••• Used in combination to treat Stomatitis Combination Product in combination with: Bacitracin (DB00626), Neomycin (DB00994) •••••••••••• ••••••• Used in combination to treat Tonsillitis Combination Product in combination with: Neomycin (DB00994), Bacitracin (DB00626) •••••••••••• ••••••• - Contraindications & Blackbox Warnings
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Like all other local anesthetics, amylocaine acts as a membrane stabilizing drug that reversibly decreases the rate of depolarization and depolarization of excitable membranes 2. In this way, the conduction of neuronal signals for certain bodily movements can be blocked 2. In particular, when administered for spinal anesthesia, the resultant anesthesia can typically extend from the chest to the legs 2.
- Mechanism of action
In particular, amylocaine, much like other local anesthetics, bind and blockade voltage gated sodium channels located in the excitable membranes of various sensory receptors 2. Once blocked, the influx of sodium across the channels and membrane is inhibited 2. Because the influx of sodium is necessary to facilitate neuronal action potentials and signal conduction across sensory receptor membranes, the influx inhibition subsequently prevents the body reactions that would normally result from the neuronal signals 2.
Target Actions Organism AVoltage-gated sodium channel alpha subunit blockerHumans - Absorption
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s 3.
- Volume of distribution
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s 3.
- Protein binding
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s 3.
- Metabolism
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s 3.
- Route of elimination
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s 3.
- Half-life
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s 3.
- Clearance
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s 3.
- Adverse Effects
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A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s 3.
- 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.Not Available
- 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.- Product Ingredients
Ingredient UNII CAS InChI Key Amylocaine hydrochloride 224EF0K14Q 532-59-2 YCAXNWFCHTZUMD-UHFFFAOYSA-N - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dentition Sirop De Syrup 180 mg / 30 mL Dental Lab Nadeau LtÉe, Division Of Technilab Inc. 1945-12-31 1999-09-28 Canada 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BASINA LOZENGE Amylocaine (0.5 MG) + Bacitracin (100 UNITS) + Neomycin (2.5 MG) Lozenge Oral บริษัท ที. แมน ฟาร์มา จำกัด 2004-08-15 2020-07-14 Thailand 
BASINA LOZENGE Amylocaine (0.5 MG) + Bacitracin (100 UNITS) + Neomycin (2.5 MG) Lozenge Oral บริษัท ที. แมน ฟาร์มา จำกัด 2003-12-17 2020-07-14 Thailand Rhino Mex Amylocaine hydrochloride (.2 %) + Naphazoline hydrochloride (.1 %) Liquid Nasal Laboratoires Charton Laboratories 1978-12-31 1999-09-17 Canada คอนนิค 99 Amylocaine (0.5 MG) + Bacitracin (100 UNITS) + Neomycin (2.5 MG) Lozenge Oral บริษัท ไบร์วู๊ดฟาร์มาซูติคอล จำกัด 1993-04-23 Not applicable Thailand บาคาล Amylocaine (0.5 MG) + Bacitracin (100 UNITS) + Neomycin (2.5 MG) Lozenge Oral บริษัท แอดวานซ์ ฟาร์มาซูติคอล แมนูเฟคเจอริ่ง จำกัด 2014-02-19 Not applicable Thailand
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
- Benzoyl derivatives / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic nitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- benzoate ester (CHEBI:34981)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- QRW683O56T
- CAS number
- 644-26-8
- InChI Key
- FDMBBCOBEAVDAO-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3
- IUPAC Name
- 1-(dimethylamino)-2-methylbutan-2-yl benzoate
- SMILES
- CCC(C)(CN(C)C)OC(=O)C1=CC=CC=C1
References
- General References
- Coleman RB: SPINAL ANAESTHESIA BY STOVAINE. Br Med J. 1925 Mar 21;1(3351):548-9. [Article]
- Butterworth JF 4th, Strichartz GR: Molecular mechanisms of local anesthesia: a review. Anesthesiology. 1990 Apr;72(4):711-34. [Article]
- Gary R. Strichartz (1987). Local Anesthetics. Springer, Berlin, Heidelberg. [ISBN:978-3-642-71112-1]
- The Wood Library-Museum: Stovaine Profile [Link]
- External Links
- KEGG Drug
- D07454
- KEGG Compound
- C14169
- PubChem Compound
- 10767
- PubChem Substance
- 310265015
- ChemSpider
- 10312
- 40660
- ChEBI
- 34981
- ChEMBL
- CHEMBL1740065
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Amylocaine
- MSDS
- Download (52.5 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Paste, dentifrice Dental Syrup Dental 180 mg / 30 mL Liquid Nasal Lozenge Oral Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.06 mg/mL ALOGPS logP 2.73 ALOGPS logP 3.22 Chemaxon logS -2.3 ALOGPS pKa (Strongest Basic) 8.91 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 29.54 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 69.68 m3·mol-1 Chemaxon Polarizability 26.96 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes 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 splash10-0a4i-9300000000-a206b658b7925ffba733 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9510000000-e3a5c8fa7ff0c8729804 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03e9-5920000000-069579006758e8ab8959 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9600000000-78b4e7a29917c1aabd09 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-9100000000-be8eb0595576560b492c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9100000000-e9387b51360ef97291e7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9300000000-e8db8a19ef0bd058f55f 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]- 156.37935 predictedDeepCCS 1.0 (2019) [M+H]+ 158.73735 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.8305 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
- Butterworth JF 4th, Strichartz GR: Molecular mechanisms of local anesthesia: a review. Anesthesiology. 1990 Apr;72(4):711-34. [Article]
- 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. [Article]
Drug created at September 15, 2015 20:30 / Updated at October 14, 2024 10:05