articaine (CED0005393)

Record Information
Version1.0
Creation Date2016-06-03 11:01:42 UTC
Update Date2026-08-19 02:08:35 UTC
SynCED IDCED0005393
Secondary Accession Numbers
  • CHEM043538
Identification
Common Namearticaine
ClassSmall Molecule
Description
Articaine is an organic compound with the chemical formula C13H20N2O3S and an average molecular weight of 284.37 g/mol. Articaine belongs to the thiophene carboxylic acids and derivatives, a subclass of thiophenes within the organic compounds. It is categorized as an organoheterocyclic compound. The compound is found in or released from four recorded sources: pharmaceuticals & veterinary products specifically as anesthetics, electrically stimulated smoking devices within electrical & electronic equipment, the preparation of wine or sparkling wine in food, food processing & cookware, and non electric simulated smoking devices in household cleaning & consumer products. Recorded exposure routes for articaine include dental, infiltration, ophthalmic, subcutaneous, and submucosal administration. At a molecular level, articaine interacts with ten recorded protein targets. It acts as an inhibitor of sodium channel protein type 1 subunit alpha (SCN1A), sodium channel protein type 4 subunit alpha (SCN4A), sodium channel protein type 5 subunit alpha (SCN5A), and sodium channel protein type 7 subunit alpha (SCN7A), in addition to six other proteins.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
CarticaineKegg
N-[2-(Methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidateGenerator
CarticainMeSH
Carticaine hydrochlorideMeSH
Hoe 045MeSH
ArticainMeSH
Hoechst brand OF carticaine hydrochlorideMeSH
Hydrochloride, carticaineMeSH
UltracaineMeSH
Hoe-045MeSH
Chemical FormulaC13H20N2O3S
Average Molecular Mass284.374 g/mol
Monoisotopic Mass284.119 g/mol
CAS Registry Number23964-58-1
IUPAC NameN-[2-(methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidic acid
Traditional Namecarticaine
SMILESCCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC
InChI IdentifierInChI=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)
InChI KeyQTGIAADRBBLJGA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiophene carboxylic acids and derivatives. Thiophene carboxylic acids and derivatives are compounds containing a thiophene ring which bears a carboxylic acid group (or a salt/ester thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiophenes
Sub ClassThiophene carboxylic acids and derivatives
Direct ParentThiophene carboxylic acids and derivatives
Alternative Parents
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
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.037 g/LALOGPS
logP1.9ALOGPS
logP0.96ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.42ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity77.53 m³·mol⁻¹ChemAxon
Polarizability30.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05g0-9710000000-17a712ab6964343fb8f4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-5190000000-2f877abe52116e1258b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-9000000000-0a18b19266dbc8f3bc9cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-91e2bdeec7aabd58a49dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-0190000000-8c22a5f16cbfcc830f1aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fl0-0590000000-3c5b853eac8c14c771b8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6s-9720000000-ad595a95bd3d6a9368deNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-96d0ca67edf9c6365a45Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-059i-9440000000-17da9b566219ea11abbdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abc-9200000000-30cacb6ff9fab18becffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0190000000-ece2126e2377c42c05a8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02ji-2940000000-aaa8465919bcdabc7df9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-5900000000-e1c427cc8b6e8e4ae1fbNot AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
3927.0 Log mg/kg [2200:7000]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
Exposure Sources
Source IDSourceSectorReference
CEDs000233Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.Personal care & cosmeticsPubChem
CEDs000369Anesthetics?Anesthetics are synthetic chemicals used to induce loss of sensation or consciousness in patients undergoing medical procedures.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000518Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.Electrical & Electronic EquipmentPubChem
CEDs000545Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.Food, food processing & cookwarePubChem
CEDs000549Preparation Of Wine Or Sparkling Wine?The preparation of wine or sparkling wine involves various stages, including fermentation, aging, and bottling, which can introduce potential sources of synthetic chemical contamination.Food, food processing & cookwarePubChem
CEDs000559Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.Household cleaning & consumer productsPubChem
CEDs000569Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.Household cleaning & consumer productsPubChem
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingPubChem
CEDs000610Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.Personal care & cosmeticsPubChem
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000617Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000632Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.Textiles, leather & furnishingsPubChem
CEDs000662Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.Textiles, leather & furnishingsPubChem
CEDs000671Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.Aviation & AerospacePubChem
CEDs000688Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.Building & ConstructionPubChem
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingPubChem
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsPubChem
Pathways
1 pathwayPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureTumor necrosis factor receptor superfamily member 6Q63199Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.239
Applicability Domain
0.239 Low confidence
Statistical Significance
0.0013
Supporting Reference Compounds
1
E-value
10.1204
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)
Prediction Confidence Score
0.226
Applicability Domain
0.253 Low confidence
Statistical Significance
0.1099
Supporting Reference Compounds
106
E-value
855.952
Fatty-acid amide hydrolase 1 structureClick to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.218
Applicability Domain
0.253 Low confidence
Statistical Significance
0.1757
Supporting Reference Compounds
102
E-value
1368.12
Click to view 3D structureBeta-1 adrenergic receptorB0FL73Cavia porcellusPredicted (SEA)
Prediction Confidence Score
0.216
Applicability Domain
0.254 Low confidence
Statistical Significance
0.0256
Supporting Reference Compounds
37
E-value
199.138
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)
Prediction Confidence Score
0.216
Applicability Domain
0.253 Low confidence
Statistical Significance
0.2916
Supporting Reference Compounds
201
E-value
2270.08
Click to view 3D structureBeta-2 adrenergic receptorQ8K4Z4Cavia porcellusPredicted (SEA)
Prediction Confidence Score
0.213
Applicability Domain
0.254 Low confidence
Statistical Significance
0.0372
Supporting Reference Compounds
48
E-value
289.755
DNA dC->dU-editing enzyme APOBEC-3G structureClick to view 3D structureDNA dC->dU-editing enzyme APOBEC-3GQ9HC16HumansPredicted (SEA)
Prediction Confidence Score
0.212
Applicability Domain
0.233 Low confidence
Statistical Significance
0.07
Supporting Reference Compounds
76
E-value
545.256
Capsid scaffolding protein structureClick to view 3D structureCapsid scaffolding proteinP03234HHV-4Predicted (SEA)
Prediction Confidence Score
0.211
Applicability Domain
0.211 Low confidence
Statistical Significance
0.0062
Supporting Reference Compounds
1
E-value
48.6558
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)
Prediction Confidence Score
0.209
Applicability Domain
0.222 Low confidence
Statistical Significance
0.281
Supporting Reference Compounds
215
E-value
2187.56
Liver carboxylesterase structureClick to view 3D structureLiver carboxylesteraseQ29550Sus scrofaPredicted (SEA)
Prediction Confidence Score
0.208
Applicability Domain
0.224 Low confidence
Statistical Significance
0.0134
Supporting Reference Compounds
20
E-value
104.474
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)
Prediction Confidence Score
0.207
Applicability Domain
0.222 Low confidence
Statistical Significance
0.4994
Supporting Reference Compounds
472
E-value
3888.18
Calpain-2 catalytic subunit structureClick to view 3D structureCalpain-2 catalytic subunitP17655HumansPredicted (SEA)
Prediction Confidence Score
0.206
Applicability Domain
0.23 Low confidence
Statistical Significance
0.0605
Supporting Reference Compounds
17
E-value
471.221
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)
Prediction Confidence Score
0.206
Applicability Domain
0.224 Low confidence
Statistical Significance
0.7614
Supporting Reference Compounds
668
E-value
5927.75
Click to view 3D structureSnake venom metalloproteinase neuwiedaseQ9I9R4Bothrops pauloensisPredicted (SEA)
Prediction Confidence Score
0.206
Applicability Domain
0.206 Low confidence
Statistical Significance
0.0268
Supporting Reference Compounds
1
E-value
208.558
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)
Prediction Confidence Score
0.205
Applicability Domain
0.215 Low confidence
Statistical Significance
0.4606
Supporting Reference Compounds
372
E-value
3585.97
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)
Prediction Confidence Score
0.204
Applicability Domain
0.225 Low confidence
Statistical Significance
0.8642
Supporting Reference Compounds
793
E-value
6728.12
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)
Prediction Confidence Score
0.203
Applicability Domain
0.215 Low confidence
Statistical Significance
0.9377
Supporting Reference Compounds
1538
E-value
7299.84
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.203
Applicability Domain
0.225 Low confidence
Statistical Significance
0.6199
Supporting Reference Compounds
541
E-value
4825.87
Click to view 3D structureAlkaline ceramidase 2Q5QJU3HumansPredicted (SEA)
Prediction Confidence Score
0.203
Applicability Domain
0.203 Low confidence
Statistical Significance
0.0404
Supporting Reference Compounds
1
E-value
314.9
Click to view 3D structureCapsid scaffolding proteinP89449Human herpesvirus 2 (strain HG52) (HHV-2) (Human herpes simplex virus2)Predicted (SEA)
Prediction Confidence Score
0.203
Applicability Domain
0.211 Low confidence
Statistical Significance
0.0033
Supporting Reference Compounds
4
E-value
26.0016
DNA repair protein REV1 structureClick to view 3D structureDNA repair protein REV1Q9UBZ9HumansPredicted (SEA)
Prediction Confidence Score
0.203
Applicability Domain
0.203 Low confidence
Statistical Significance
0.0168
Supporting Reference Compounds
1
E-value
131.098
Beta-1 adrenergic receptor structureClick to view 3D structureBeta-1 adrenergic receptorP08588HumansPredicted (SEA)
Prediction Confidence Score
0.203
Applicability Domain
0.225 Low confidence
Statistical Significance
0.4299
Supporting Reference Compounds
180
E-value
3347.05
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)
Prediction Confidence Score
0.203
Applicability Domain
0.222 Low confidence
Statistical Significance
0.4979
Supporting Reference Compounds
407
E-value
3875.8
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)
Prediction Confidence Score
0.202
Applicability Domain
0.211 Low confidence
Statistical Significance
0.706
Supporting Reference Compounds
497
E-value
5496.23
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)
Prediction Confidence Score
0.202
Applicability Domain
0.203 Low confidence
Statistical Significance
0.8704
Supporting Reference Compounds
1130
E-value
6775.68
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID29837
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available