Articaine

Identification

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Name
Articaine
Accession Number
DB09009
Type
Small Molecule
Groups
Approved
Description

Articaine is a dental local anesthetic. Articaine is widely used around the world and is the most popular local anesthetic in many European countries.

Structure
Thumb
Synonyms
  • Articaína
  • Articaine
  • Articainum
External IDs
HOE 045
Product Ingredients
IngredientUNIICASInChI Key
Articaine hydrochlorideQS9014Q79223964-57-0GDWDBGSWGNEMGJ-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Articaine hydrochloride (40 mg) + Epinephrine (0.005 mg)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Articaine hydrochloride (40 mg) + Epinephrine (0.005 mg)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Articaine hydrochloride (40 mg) + Epinephrine (0.01 mg)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Articaine hydrochloride (40 mg) + Epinephrine (0.01 mg)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada
ArticadentArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL)Injection, solutionSubcutaneousDentsply Pharmaceutical2000-04-03Not applicableUs
ArticadentArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.01 mg/1mL)Injection, solutionSubcutaneousDentsply Pharmaceutical2000-04-03Not applicableUs
ArticaineArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.01 mg/1mL)Injection, solutionSubcutaneousPatterson Dental2014-12-22Not applicableUs
ArticaineArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL)Injection, solutionSubcutaneousDarby Dental Supply Llc2017-03-012018-01-02Us
ArticaineArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.005 mg/1mL)Injection, solutionSubcutaneousPatterson Dental2014-12-22Not applicableUs
ArticaineArticaine hydrochloride (40 mg/1mL) + Epinephrine bitartrate (0.01 mg/1mL)Injection, solutionSubcutaneousDarby Dental Supply Llc2017-03-012018-01-02Us
International/Other Brands
Septanest / Septocaine / Ultracaine
Categories
UNII
D3SQ406G9X
CAS number
23964-58-1
Weight
Average: 284.374
Monoisotopic: 284.119463206
Chemical Formula
C13H20N2O3S
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Toxicity
Not Available
Affected organisms
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
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Articaine.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Articaine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Articaine.
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Articaine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be decreased when used in combination with Articaine.
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Articaine.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Articaine.
AMG-222The therapeutic efficacy of AMG-222 can be decreased when used in combination with Articaine.
AnagliptinThe therapeutic efficacy of Anagliptin can be decreased when used in combination with Articaine.
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Articaine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

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
ChEBI
91834
ChEMBL
CHEMBL1093
Drugs.com
Drugs.com Drug Page
Wikipedia
Articaine
ATC Codes
N01BB58 — Articaine, combinationsN01BB08 — Articaine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentRenal Failure1
0Not Yet RecruitingPreventionPulpitis - Irreversible1
1CompletedTreatmentOvercoming the Failure of Anesthesia in the Mandibular Teeth1
1RecruitingHealth Services ResearchSurgery, Hand / Upper Limb Surgery1
1, 2Not Yet RecruitingOtherBehaviour Assessment / Pain1
2SuspendedTreatmentApical Periodontitis / Caries,Dental3
3CompletedTreatmentIrreversible Pulpitis1
3CompletedTreatmentSpinal Anaesthesia2
4CompletedHealth Services ResearchAdverse Reaction to Other Local Anesthetics / Impacted Third Molar Tooth1
4CompletedOtherPeriodontitis1
4CompletedPreventionAnesthesia of Mucous Membrane1
4CompletedSupportive CarePain1
4CompletedTreatmentGastroscopy1
4CompletedTreatmentIrreversible Pulpitis1
4CompletedTreatmentIrreversible Pulpitis / Pain1
4CompletedTreatmentLocal Anesthesia of the Skin3
4Enrolling by InvitationHealth Services ResearchDrug Effect / Tooth Extractions1
4Not Yet RecruitingTreatmentAnesthesia, Dental / Postoperative pain1
4Not Yet RecruitingTreatmentSymptomatic Irreversible Pulpitis1
4RecruitingTreatmentAnesthesia Complications / Anesthesia Morbidity / Dental Implant Failed / Surgical Complications From Local Anesthesia1
4SuspendedTreatmentAortic Valve Disorder / Atrial Septal Defect (ASD) / Diseases of Mitral Valve / Intracardiac Myxoma1
4TerminatedTreatmentCicatrix1
4WithdrawnTreatmentLocal Anesthesia1
Not AvailableCompletedPreventionHypotension1
Not AvailableCompletedTreatmentAcetaminophen / Analgesia / Curettage / Paracervical Block1
Not AvailableCompletedTreatmentPulpitis dental1
Not AvailableNot Yet RecruitingTreatmentBadly Decayed Lower First Primary Molars in Children / Badly Decayed Lower Primary Molars in Children1
Not AvailableNot Yet RecruitingTreatmentLocal Anesthesia1
Not AvailableRecruitingTreatmentAnesthesia, Dental / Tooth Extractions1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InjectionSubmucosal
Injection, solutionDental; Infiltration
LiquidInfiltration
Injection, solutionSubcutaneous
Injection, solutionSubmucosal
SolutionInfiltration
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

Taxonomy

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
Thiophene carboxylic acid or derivatives / Methyl ester / Heteroaromatic compound / Amino acid or derivatives / Carboxylic acid ester / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid derivative / Secondary aliphatic amine / Monocarboxylic acid or derivatives
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on June 20, 2014 11:45 / Updated on January 17, 2020 00:44