Basic information
- CAS
23964-58-1- Standard SMILES
CCCNC(C)C(=O)Nc1c(C)csc1C(=O)OC- InChIKey
QTGIAADRBBLJGA-UHFFFAOYSA-N- Molecular formula
- C13H20N2O3S
- Average molar mass
- 284.38 g/mol
- Monoisotopic mass
- 284.11946368
Overview
4-methyl-3-[[1-oxo-2-(propylamino)propyl]amino]-2-thiophenecarboxylic acid methyl ester is a thiophenecarboxylic acid.
Names & identifiers
- Preferred name
- Articaine
- IUPAC
- methyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate
- English name
- Articaine
- Molecular formula
- C13H20N2O3S
- Molecular weight
- 284.37
Names & synonyms
Articaine23964-58-1CarticaineArticainaArticainumArticadentArticainCarticainOrablocUltacanD3SQ406G9Xmethyl 4-methyl-3-[2-(propylamino)propanamido]thiophene-2-carboxylate
Show more names
ARTICAINE HCL40045atecaineUnii-D3sq406G9xArticaine (USP)
DTXSID7048536methyl 4-methyl-3-(2-(propylamino)propanamido)thiophene-2-carboxylate2-Thiophenecarboxylic acid, 4-methyl-3-((1-oxo-2-(propylamino)propyl)amino)-, methyl esterUltacan ForteHydrochloride, CarticaineRefChem:388864Septocaine and EpinephrineArticaine HCl and Epinephrine
Database identifiers
- CAS
23964-58-1- PubChem CID
- 32170
- DTXSID
DTXSID7048536- ChEMBL
CHEMBL1093- ChEBI
CHEBI:91834- UNII
- D3SQ406G9X
- EC Number
- 607-295-0
- Nikkaji
- J342.299B
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 95.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 325
Experimental & physicochemical properties
DrugsPharmaceuticals
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anesthetics, Local
FDA approved drugs -> Active ingredient
Pharmaceuticals
Melting Point172-173
Physicochemical properties
- Melting point
- 175 · 175-176 °C
- Boiling point
- 0.3 · bp0.3 162-167°
- Density
- 1.178 · 1.178±0.06 g/cm3(Predicted)
- storage temp.
- Refrigerator
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 13.46 · 13.46±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- Major Application
- pharmaceutical (small molecule)
- 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)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- WGK 3
- hs_code
- 2934990002
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
ATC Code
N01BB58
N - Nervous system
QN - Nervous system
FDA Pharmacological Classification
D3SQ406G9X
ARTICAINE
Established Pharmacologic Class [EPC] - Amide Local Anesthetic
Chemical Structure [CS] - Amides
Physiologic Effects [PE] - Local Anesthesia
Articaine is an Amide Local Anesthetic. The physiologic effect of articaine is by means of Local Anesthesia.
MeSH Pharmacological Classification
Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >100
Use ClassificationPharmaceuticals
Applications
DescriptionArticaine [4-methyl-3-(2-propylaminopropionamido) thiophene-2-carboxylic acid methyl ester hydrochloride] has been widely used in dentistry since its approval by the U.S. FDA in the year 2000 because of its quick onset and short duration of action. The structure of articaine differs from those of all other amino amide-type local anesthetics in that it contains a thiophene ring instead of a benzene ring and a carbomethoxy group. This renders the molecule more lipophilic and, thus, easier to cross any lipoidal membranes. Its local anesthetic potency is approximately 1.5-fold that of lidocaine, even though it has similar pKa (7.8) and plasma protein binding (76%) properties. Articaine also is metabolized primarily by plasma cholinesterases because of the presence of an ester group and, therefore, has a much shorter duration of action than lidocaine (i.e., only approximately one-fourth that of lidocaine). Articaine undergoes rapid hydrolysis of the carbomethoxy group to give articainic acid, which is eliminated either unchanged (75%) or as its glucuronides (25%). Compared with to other shortacting, amino amide-type local anesthetics, such as mepivacaine, lidocaine, or prilocaine, articaine is said to be a much safer drug for regional anesthesia and is the drug of choice for dental procedures.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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