| Identification | More | [Name]
Articaine | [CAS]
23964-58-1 | [Synonyms]
ARTICAINE
ARTICAINE HCL
ARTICAINE HYDROCHLORIDE
methyl 4-methyl-3-(2-propylaminopropanoylamino)thiophene-2-carboxylate
4-Methyl-3-[2-[propylamino] propionamido]-2-thiophenecarboxylic acid, methyl ester
Carticaine
40045
4-Methyl-3-[[1-oxo-2-(propylamino)propyl]amino]-2-thiophenecarboxylic acid methyl ester
4-Methyl-3-[1-oxo-2-(propylamino)propylamino]-2-thiophenecarboxylic acid methyl ester | [EINECS(EC#)]
607-295-0 | [Molecular Formula]
C13H21ClN2O3S | [MDL Number]
MFCD00190157 | [Molecular Weight]
320.84 | [MOL File]
23964-58-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
175-176 °C | [Boiling point ]
bp0.3 162-167° | [density ]
1.178±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.46±0.70(Predicted) | [color ]
White to Off-White | [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) | [Contact allergens]
This local amide-type anesthetic is seldom reported as
allergenic even in patients sensitized to other amidetype
molecules like lidocaine, prilocaine, mepivacaine,
or bupivacaine. | [InChIKey]
QTGIAADRBBLJGA-UHFFFAOYSA-N | [SMILES]
C1(C(OC)=O)SC=C(C)C=1NC(=O)C(NCCC)C | [CAS DataBase Reference]
23964-58-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
Articaine is an amide based short-acting local anesthetic use for regional anaesthesia in day-case settings such arthroscopy, hand , food surgery and in dentistry. | [Description]
Articaine [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. | [Originator]
Ultracain,Hoechst,W. Germany,1976 | [Definition]
ChEBI: 4-methyl-3-[[1-oxo-2-(propylamino)propyl]amino]-2-thiophenecarboxylic acid methyl ester is a thiophenecarboxylic acid. | [Manufacturing Process]
3-α-Chloropropionylamino-2-carbomethoxy-4-methylthiophene (prepared from
3-amino-2-carbomethoxy-4-methylthiophene and chloropropionyl chloride)
was dissolved in toluene and n-propylamine added. The whole mixture was
heated to boiling for 6 to 7 hours. After cooling, the propylamine
hydrochloride that had formed was removed by washing with water, The
toluene phase was dried with sodium sulfate, and then the solvent and excess
propylamine were removed by distillation. The oily residue was taken up in
ether. The hydrochloride of 3-n-propylamino-α-propionylamino-2-
carbomethoxy-4-methylthiophene was obtained by introducing hydrogen
chloride gas or by means of methanolic hydrogen chloride. The base boils at
162°C to 167°C under 0.3 mm of mercury pressure and the hydrochloride
melts at 177°C to 178°C. | [Therapeutic Function]
Local anesthetic |
|
|