Articaine hydrochloride
[CAS# 23964-57-0]

Identification

• Classification: Analytical chemistry >> Standard >> Pharmacopoeia standards and magazine standards
• Name: Articaine hydrochloride
• Synonyms: Methyl 4-methyl-3-(2-propylaminopropanoylamino)thiophene-2-carboxylate hydrochloride
• Molecular Formula: C₁₃H₂₀N₂O₃S^.HCl
• Molecular Weight: 320.83
• CAS Registry Number: 23964-57-0
• EC Number: 245-957-7
• SMILES: CCCNC(C)C(=O)NC1=C(SC=C1C)C(=O)OC.Cl

Properties

• Solubility: DMSO 64 mg/mL, Water 64 mg/mL (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P305-P351-P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

Articaine hydrochloride is an amide-type local anesthetic widely used in dental and oral surgical procedures. It works by reversibly blocking voltage-gated sodium channels in nerve membranes, thereby inhibiting the initiation and propagation of nerve impulses, which results in a localized loss of sensation. Articaine is noted for its rapid onset, intermediate duration of action, and enhanced tissue penetration compared to other local anesthetics.

Articaine was first synthesized in the 1970s and introduced clinically in the 1980s. It differs structurally from most other amide anesthetics by containing a thiophene ring instead of a benzene ring, which increases its lipid solubility and enhances diffusion through nerve membranes and soft tissues. Additionally, articaine possesses an ester group that undergoes hydrolysis in the plasma, leading to a unique metabolic pathway that results in a shorter systemic half-life than many other amide anesthetics.

The hydrochloride salt of articaine improves its solubility and stability for injectable solutions. It is commonly formulated in concentrations of 4%, often combined with epinephrine as a vasoconstrictor to prolong anesthetic duration and reduce systemic absorption. Articaine is favored in dentistry for infiltrative anesthesia due to its ability to penetrate dense cortical bone more effectively, reducing the need for nerve blocks in some cases.

Clinically, articaine hydrochloride is extensively used for dental procedures such as tooth extractions, root canal treatments, and minor oral surgeries. Its rapid onset, usually within 1 to 3 minutes, and intermediate duration of anesthesia, approximately 1 to 2 hours with vasoconstrictor, allow for efficient procedural workflow and patient comfort. The faster metabolism due to plasma ester hydrolysis decreases the risk of systemic toxicity, making it suitable for use in patients requiring multiple injections.

Pharmacokinetically, articaine is absorbed rapidly from the injection site and is extensively metabolized both in the liver and by plasma esterases. The primary metabolites are inactive and eliminated primarily via renal excretion. The elimination half-life is approximately 20 minutes, significantly shorter than other amide anesthetics, contributing to its safety profile.

Adverse effects of articaine hydrochloride are generally consistent with those of other local anesthetics and include local reactions, such as pain or swelling at the injection site, and systemic effects in rare cases of overdose or intravascular injection. Some reports have raised concerns about a slightly higher incidence of nerve injury, particularly lingual nerve paresthesia, although this remains a subject of clinical investigation and debate.

In summary, articaine hydrochloride is a widely used amide local anesthetic characterized by rapid onset, effective tissue penetration, and a unique metabolic profile involving both hepatic and plasma metabolism. Its favorable pharmacokinetics and clinical efficacy make it a preferred agent in dental anesthesia, providing effective pain control with a generally safe profile when used appropriately.

References

1980. Carticaine: Action of the local anesthetic on myelinated nerve fibres. European Journal of Pharmacology, 62(1).
DOI: 10.1016/0014-2999(80)90482-3

2024. The efficacy of articaine in pain management during endodontic procedures in pediatric patients. Perioperative Medicine, 13(1).
DOI: 10.1186/s13741-024-00389-5

2024. Comparative efficacy of topical lidocaine, tetracaine, and articaine for post-tonsillectomy pain management in children: a prospective, placebo-controlled study. Acta Oto-Laryngologica, 144(5).
DOI: 10.1080/00016489.2024.2372298