Identification
- Summary
Articaine is a local anesthetic used for inducing local, infiltrative, or conductive anesthesia in both simple and complex dental procedures.
- Brand Names
- Articadent, Astracaine, Orabloc, Septanest, Septocaine, Ultacan, Ultracaine, Zorcaine
- Generic Name
- Articaine
- DrugBank Accession Number
- DB09009
- Background
Articaine is a dental local anesthetic. Articaine is widely used around the world and is the most popular local anesthetic in many European countries.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Articaine (DB09009)
- Weight
- Average: 284.374
Monoisotopic: 284.119463206 - Chemical Formula
- C13H20N2O3S
- Synonyms
- Articaína
- Articaine
- Articainum
- External IDs
- HOE 045
Pharmacology
- Indication
Not Available
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Articaine is combined with 1,2-Benzodiazepine. Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Articaine. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Articaine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Articaine. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Articaine. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Articaine. Aclidinium Articaine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Agomelatine is combined with Articaine. Albiglutide The therapeutic efficacy of Albiglutide can be decreased when used in combination with Articaine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Articaine. 
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- 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 Articaine hydrochloride QS9014Q792 23964-57-0 GDWDBGSWGNEMGJ-UHFFFAOYSA-N - International/Other Brands
- Septanest / Septocaine / Ultracaine
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml) Articaine hydrochloride (40 mg / mL) + Epinephrine bitartrate (0.005 mg / mL) Solution Infiltration Dentsply Pharmaceutical 2004-01-29 Not applicable Canada 
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml) Articaine hydrochloride (40 mg / mL) + Epinephrine (0.005 mg / mL) Solution Infiltration Dentsply Pharmaceutical 1997-02-26 2003-11-28 Canada 4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml) Articaine hydrochloride (40 mg / mL) + Epinephrine bitartrate (0.01 mg / mL) Solution Infiltration Dentsply Pharmaceutical 2004-01-29 Not applicable Canada 4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml) Articaine hydrochloride (40 mg / mL) + Epinephrine (0.01 mg / mL) Solution Infiltration Dentsply Pharmaceutical 1997-02-26 2003-11-28 Canada ARTHEEK SP® Articaine hydrochloride (40 mg) + Epinephrine (0.01 mg) Solution Dental PRODUCTORA Y COMERCIALIZADORA ODONTOLOGICANEW STETIC S.A. 2015-04-30 Not applicable Colombia 
Articadent Articaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL) Injection, solution Infiltration; Submucosal Dentsply Pharmaceutical 2000-04-03 Not applicable US 
Articadent Articaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.01 mg/1mL) Injection, solution Infiltration; Submucosal Dentsply Pharmaceutical 2000-04-03 Not applicable US Articaine Articaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.01 mg/1mL) Injection, solution Infiltration; Submucosal NDC, Inc. 2015-06-22 Not applicable US Articaine Articaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.01 mg/1mL) Injection, solution Infiltration; Submucosal Patterson Dental 2014-12-22 Not applicable US Articaine Articaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL) Injection, solution Infiltration; Submucosal Benco Dental 2016-04-04 Not applicable US
Categories
- ATC Codes
- N01BB58 — Articaine, combinationsN01BB08 — Articaine
- Drug Categories
- Amides
- Anesthetics
- Anesthetics, Local
- Central Nervous System Agents
- Central Nervous System Depressants
- Hyperglycemia-Associated Agents
- Local Anesthesia
- Local Anesthetics (Amide)
- Methemoglobinemia Associated Agents
- Nervous System
- Peripheral Nervous System Agents
- Sensory System Agents
- Sulfur Compounds
- Thiophenes
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as thiophene carboxylic acids and derivatives. These are compounds containing a thiophene ring which bears a carboxylic acid group (or a salt/ester thereof).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Thiophenes
- Sub Class
- Thiophene carboxylic acids and derivatives
- Direct Parent
- Thiophene carboxylic acids and derivatives
- Alternative Parents
- Methyl esters / Heteroaromatic compounds / Amino acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Dialkylamines / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Organic oxides show 1 more
- Substituents
- Amine / Amino acid or derivatives / Aromatic heteromonocyclic compound / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid derivative / Carboxylic acid ester / Heteroaromatic compound / Hydrocarbon derivative / Methyl ester show 12 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- D3SQ406G9X
- CAS number
- 23964-58-1
- InChI Key
- QTGIAADRBBLJGA-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H20N2O3S/c1-5-6-14-9(3)12(16)15-10-8(2)7-19-11(10)13(17)18-4/h7,9,14H,5-6H2,1-4H3,(H,15,16)
- IUPAC Name
- methyl 4-methyl-3-[2-(propylamino)propanamido]thiophene-2-carboxylate
- SMILES
- CCCNC(C)C(=O)NC1=C(SC=C1C)C(=O)OC
References
- Synthesis Reference
U.S. Patent 3,910,924.
- General References
- Not Available
- External Links
- KEGG Drug
- D07468
- PubChem Compound
- 32170
- PubChem Substance
- 310264968
- ChemSpider
- 29837
- BindingDB
- 50225496
- 592464
- ChEBI
- 91834
- ChEMBL
- CHEMBL1093
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Articaine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Anesthesia Complications / Anesthesia Morbidity / Dental Implant Failed / Surgical Complications From Local Anesthesia 1 4 Completed Health Services Research Adverse Reaction to Other Local Anesthetics / Impacted Third Molar Tooth 1 4 Completed Health Services Research Effect of Drugs / Tooth Extractions 1 4 Completed Other Periodontitis 1 4 Completed Prevention Anesthesia of Mucous Membrane 1 4 Completed Supportive Care Pain 1 4 Completed Treatment Anesthetic Effectiveness 1 4 Completed Treatment Dental Extraction / Maxillary Teeth / Overcoming the Failure of Anaesthesia 1 4 Completed Treatment Gastroscopy 1 4 Completed Treatment Irreversible Pulpitis (Toothache) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Dental Injection, solution Parenteral Injection, solution Subcutaneous Injection Infiltration; Submucosal Injection, solution Dental; Infiltration Solution Injection, solution Infiltration Injection Dental 40 mg/ml Solution Dental Injection Dental Injection, solution Submucosal Injection Injection, solution Dental 40 mg/ml Injection, solution Buccal Solution Infiltration Solution Infiltration 0.009 mg Injection, solution Infiltration; Perineural Injection, solution Infiltration; Submucosal Injection Submucosal 40 mg/ml Liquid Infiltration - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 172-173 U.S. Patent 3,910,924. - Predicted Properties
Property Value Source Water Solubility 0.0285 mg/mL ALOGPS logP 1.93 ALOGPS logP 3.25 ChemAxon logS -4 ALOGPS pKa (Strongest Acidic) 11.61 ChemAxon pKa (Strongest Basic) 8.68 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 67.43 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 76.78 m3·mol-1 ChemAxon Polarizability 30.54 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 Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at June 20, 2014 17:45 / Updated at January 02, 2022 12:00