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
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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Associated Therapies
Contraindications & Blackbox Warnings
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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
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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 CNS depression can be increased when Articaine is combined with 1,2-Benzodiazepine.
AbemaciclibThe risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Articaine.
AbirateroneThe risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Articaine.
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.
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 bitartrate (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 Pharmaceutical1997-02-262003-11-28Canada flag
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Articaine hydrochloride (40 mg / mL) + Epinephrine bitartrate (0.01 mg / mL)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada flag
ALFACAINAArticaine hydrochloride (72 MG/1.8ML) + Epinephrine (0.0099 MG/1.8ML)Injection, solutionDentalDentsply Sirona Italia S.R.L.2014-07-082022-04-01Italy 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
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4Active Not RecruitingTreatmentAnesthesia Morbidity / Anesthetics Adverse Reaction / Dental Implant Failed / Surgical Complications From Local Anesthesia1somestatusstop reasonjust information to hide
4CompletedHealth Services ResearchAdverse Reaction to Other Local Anesthetics / Impacted Third Molar Tooth1somestatusstop reasonjust information to hide
4CompletedHealth Services ResearchEffect of Drugs / Tooth Extractions1somestatusstop reasonjust information to hide
4CompletedOtherPeriodontitis1somestatusstop reasonjust information to hide
4CompletedPreventionAnesthesia of Mucous Membrane1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionSubcutaneous
SolutionDental
Injection, solutionParenteral
Injection, solutionDental
Injection, solutionSubcutaneous
InjectionInfiltration; Submucosal
Injection, solutionDental; Infiltration
Injection, solutionBuccal
Solution
Injection, solutionInfiltration
InjectionDental
SolutionSubcutaneous72.000 mg
Injection
SolutionInfiltration
Injection, solutionInfiltration; Perineural
Injection, solutionInfiltration; Submucosal
SolutionParenteral
InjectionSubmucosal40 mg/ml
Injection, solutionSubmucosal
LiquidInfiltration
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-MSsplash10-05g0-9710000000-17a712ab6964343fb8f4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-3490000000-8859bb2dd2e5451c1f0c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0190000000-db23d3d742022e0d3561
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05g0-9240000000-85648fe600a21936cecc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-069s-3950000000-dce159a5f0e68ad74bfc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05tf-9720000000-add2345f9d530d30b502
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-3920000000-3117c043b921eaf2443a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-161.26118
predicted
DeepCCS 1.0 (2019)
[M+H]+163.61922
predicted
DeepCCS 1.0 (2019)
[M+Na]+169.71248
predicted
DeepCCS 1.0 (2019)

Drug created at June 20, 2014 17:45 / Updated at May 03, 2024 10:13