Articaine

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
Thumb
Weight
Average: 284.374
Monoisotopic: 284.119463206
Chemical Formula
C13H20N2O3S
Synonyms
  • Articaína
  • Articaine
  • Articainum
External IDs
  • HOE 045

Pharmacology

Indication

Not Available

Pharmacology
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Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Articaine is combined with 1,2-Benzodiazepine.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Articaine.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Articaine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Articaine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Articaine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Articaine.
AclidiniumArticaine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Articaine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be decreased when used in combination with Articaine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Articaine.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Articaine hydrochlorideQS9014Q79223964-57-0GDWDBGSWGNEMGJ-UHFFFAOYSA-N
International/Other Brands
Septanest / Septocaine / Ultracaine
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Articaine hydrochloride (40 mg / mL) + Epinephrine (0.005 mg / mL)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada flag
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Articaine hydrochloride (40 mg / mL) + Epinephrine (0.005 mg / mL)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada flag
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Articaine hydrochloride (40 mg / mL) + Epinephrine (0.01 mg / mL)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada flag
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Articaine hydrochloride (40 mg / mL) + Epinephrine (0.01 mg / mL)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada flag
ARTHEEK SP®Articaine hydrochloride (72 mg) + Epinephrine (0.018 mg)SolutionDentalPRODUCTORA Y COMERCIALIZADORA ODONTOLOGICANEW STETIC S.A.2015-04-30Not applicableColombia flag
ArticadentArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL)Injection, solutionInfiltration; SubmucosalDentsply Pharmaceutical2000-04-03Not applicableUS flag
ArticadentArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.01 mg/1mL)Injection, solutionInfiltration; SubmucosalDentsply Pharmaceutical2000-04-03Not applicableUS flag
ArticaineArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL)Injection, solutionInfiltration; SubmucosalNDC, Inc.2015-12-04Not applicableUS flag
ArticaineArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL)Injection, solutionInfiltration; SubmucosalPatterson Dental2014-12-22Not applicableUS flag
ArticaineArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL)Injection, solutionSubcutaneousDarby Dental Supply Llc2017-03-012018-01-02US flag

Categories

ATC Codes
N01BB58 — Articaine, combinationsN01BB08 — Articaine
Drug Categories
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
KEGG Drug
D07468
PubChem Compound
32170
PubChem Substance
310264968
ChemSpider
29837
BindingDB
50225496
RxNav
592464
ChEBI
91834
ChEMBL
CHEMBL1093
Drugs.com
Drugs.com Drug Page
Wikipedia
Articaine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAnesthesia Complications / Anesthesia Morbidity / Dental Implant Failed / Surgical Complications From Local Anesthesia1
4CompletedHealth Services ResearchAdverse Reaction to Other Local Anesthetics / Impacted Third Molar Tooth1
4CompletedHealth Services ResearchEffect of Drugs / Tooth Extractions1
4CompletedOtherPeriodontitis1
4CompletedPreventionAnesthesia of Mucous Membrane1
4CompletedSupportive CarePain1
4CompletedTreatmentAnesthetic Effectiveness1
4CompletedTreatmentDental Extraction / Maxillary Teeth / Overcoming the Failure of Anaesthesia1
4CompletedTreatmentGastroscopy1
4CompletedTreatmentIrreversible Pulpitis (Toothache)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionDental
SolutionInfiltration
Injection, solutionSubcutaneous
InjectionInfiltration; Submucosal
Injection, solutionDental; Infiltration
Solution
Injection, solutionInfiltration
SolutionDental
InjectionDental
Injection
Injection, solutionParenteral
Injection, solutionBuccal
Injection, solutionInfiltration; Perineural
LiquidInfiltration
Injection, solutionInfiltration; Submucosal
Injection, solutionSubmucosal
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)172-173U.S. Patent 3,910,924.
Predicted Properties
PropertyValueSource
Water Solubility0.0285 mg/mLALOGPS
logP1.93ALOGPS
logP3.25ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)11.61ChemAxon
pKa (Strongest Basic)8.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.43 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity76.78 m3·mol-1ChemAxon
Polarizability30.54 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Drug created on June 20, 2014 17:45 / Updated on May 19, 2021 03:45