Articaine

Last updated
Articaine
Articaine.svg
Articaine-3D-spacefill.png
Clinical data
Other namesCarticaine
AHFS/Drugs.com Monograph
Routes of
administration 		Subcutaneous, submucosal, parenteral, epidural, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver, plasma
Elimination half-life 30 min
Excretion Liver and unspecific plasma estearases [1]
Identifiers
  • (RS)-Methyl 4-methyl-3-(2-propylaminopropanoylamino)thiophene-2-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.115.711 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C13H20N2O3S
Molar mass 284.37 g/mol
320.836 g/mol (HCl) g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • O=C(Nc1c(scc1C)C(=O)OC)C(NCCC)C
  • 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) Yes check.svgY
  • Key:QTGIAADRBBLJGA-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Articaine is a dental amide-type local anesthetic. It is the most widely used local anesthetic in a number of European countries [2] and is available in many countries. It is the only local anaesthetic to contain a thiophene ring, meaning it can be described as 'thiophenic'; this conveys lipid solubility. [3]

Contents

History

This drug was synthesized by pharmacologist Roman Muschaweck  [ de ] and chemist Robert Rippel. [4] Muschaweck received a "O. Schmiedeberg" medal by the German Society for Experimental and Clinical Pharmacology and Toxicology for his work in 2002. [5] It was brought to the German market in 1976 by Hoechst AG, a life-sciences German company (now Sanofi-Aventis), under the brand name Ultracain. [4] [6] This drug was also referred to as "carticaine" until 1984. [7] : 71 

In 1983 it was brought into the North American market, to Canada, under the name Ultracaine for dental use, manufactured in Germany and distributed by Hoechst-Marion-Roussel. This brand is currently manufactured in Germany by Sanofi-Aventis and distributed in North America by Hansamed Limited (since 1999). After Ultracaine's patent protection expired, new generic versions arrived to the Canadian market: (in order of appearance) Septanest (Septodont), Astracaine, (originally by AstraZeneca and now a Dentsply product), Zorcaine (Carestream Health/Kodak) and Orabloc (Pierrel).

It was approved by the FDA in April 2000, and became available in the United States of America two months later under the brand name Septocaine, an anesthetic/vasoconstrictor combination with Epinephrine 1:100,000 (trade name Septodont). Zorcaine became available there a few years later, also. Articadent (Dentsply) became available in the United States in October 2010. The three brands currently available in the United States are all manufactured for these companies by Novocol Pharmaceuticals Inc. (Canada). Ubistesin and Ubistesin Forte (3M ESPE) are also widely used in the United States and Europe. Orabloc (Pierrel) is aseptically manufactured and was approved by the FDA in 2010, became available in Canada in 2011, and in Europe from 2013.

Articaine is currently available for the North American dental market:

An epinephrine-free (adrenaline-free) version is available in Europe under the brand name Ultracain D. However, version with epinephrine (adrenaline) is available in Europe under the brand name Supracain 4% with epinephrine concentration of 1:200,000.

Structure and metabolism

The amide structure of articaine is similar to that of other local anesthetics, but its molecular structure differs through the presence of a thiophene ring instead of a benzene ring. Articaine is exceptional because it contains an additional ester group that is metabolized by esterases in blood and tissue. [2] The elimination of articaine is exponential with a half-life of 20 minutes. [8] [9] Since articaine is hydrolized very quickly in the blood, the risk of systemic intoxication seems to be lower than with other anesthetics, especially if repeated injection is performed. [1]

Clinical use

Articaine is used for pain control. Like other local anesthetic drugs, articaine causes a transient and completely reversible state of anesthesia (loss of sensation) during (dental) procedures. [7] : 3 

In dentistry, articaine is used mainly for infiltration injections. Articaine, while not proven, has been associated with higher risk of nerve damage when used as a block technique. [10] However, articaine is able to penetrate dense cortical bone — as found in the lower jaw (mandible) — more than most other local anaesthetics.

In people with hypokalemic sensory overstimulation, lidocaine is not very effective, but articaine works well. [11]

Studies comparing lidocaine and articaine found that articaine is more effective than lidocaine in anaesthetising the posterior first molar region. [12] Articaine has been found to be 3.81 times more likely than lidocaine to produce successful anaesthesia when used for infiltration injections. However, there is no evidence to support the use of articaine over lidocaine for inferior alveolar nerve blocks. [13] Furthermore, articaine has been demonstrated to be superior to lidocaine for use of supplementary infiltration following persistent pain despite a successful inferior dental nerve block with lidocaine. [14]

Contraindications

Articaine is not contraindicated in patients with sulfa allergies, as there is no cross-allergenicity between articaine's sulphur-bearing thiophene ring and sulfonamides. [16]

Methylparaben is no longer present in any dental local anesthetic formula available in North America. [7] : 73 

Paresthesia controversy

Paresthesia, a short-to-long-term numbness or altered sensation affecting a nerve, is a well-known complication of injectable local anesthetics and has been present even before articaine was available. [17]

An article by Haas and Lennon published in 1993 [18] seems to be the original source for the controversy surrounding articaine. This paper analyzed 143 cases reported in to the Royal College of Dental Surgeons of Ontario (RCDSO) over a 21-year period. The results from their analysis seemed to indicate that 4% local anesthetics had a higher incidence of causing paresthesia, an undesirable temporary or permanent complication, after the injection. The authors concluded that “...the overall incidence of paresthesia following local anesthetic administration for non-surgical procedures in dentistry in Ontario is very low, with only 14 cases being reported out of an estimated 11,000,000 injections in 1993. However if paresthesia does occur, the results of this study are consistent with the suggestion that it is significantly more likely to do so if either articaine or prilocaine is used.”

In another paper by the same authors, [19] 19 reported paresthesia cases in Ontario for 1994 were reviewed, concluding that the incidence of paresthesia was 2.05 per million injections of 4% anesthetic drugs. Another follow up study by Miller and Haas published in 2000, [20] concluded that the incidence of paresthesia from either prilocaine or articaine (the only two 4% drugs in the dental market) was close to 1:500,000 injections. (An average dentist gives around 1,800 injections in a year). [21]

Almost all recorded cases of long-term numbness or altered sensation (paresthesia) seem only to be present when this anesthetic is used for dental use (no PubMed references for paresthesia with articaine for other medical specialties). Also, in the vast majority of the reports, only the lingual nerve was affected.

Nonetheless, direct damage to the nerve caused by 4% drugs has never been scientifically proven. [22]

Some research points to needle trauma as the cause of the paresthesia events. [10] [23]

Related Research Articles

Local anesthesia is any technique to induce the absence of sensation in a specific part of the body, generally for the aim of inducing local analgesia, i.e. local insensitivity to pain, although other local senses may be affected as well. It allows patients to undergo surgical and dental procedures with reduced pain and distress. In many situations, such as cesarean section, it is safer and therefore superior to general anesthesia.

<span class="mw-page-title-main">Local anesthetic</span> Medications to reversibly block pain

A local anesthetic (LA) is a medication that causes absence of all sensation in a specific body part without loss of consciousness, as opposed to a general anesthetic, which eliminates all sensation in the entire body and causes unconsciousness. Local anesthetics are most commonly used to eliminate pain during or after surgery. When it is used on specific nerve pathways, paralysis also can be induced.

<span class="mw-page-title-main">Procaine</span> Local anesthetic drug

Procaine is a local anesthetic drug of the amino ester group. It is most commonly used in dental procedures to numb the area around a tooth and is also used to reduce the pain of intramuscular injection of penicillin. Owing to the ubiquity of the trade name Novocain or Novocaine, in some regions, procaine is referred to generically as novocaine. It acts mainly as a sodium channel blocker. Today, it is used therapeutically in some countries due to its sympatholytic, anti-inflammatory, perfusion-enhancing, and mood-enhancing effects.

<span class="mw-page-title-main">Lidocaine</span> Local anesthetic

Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia. When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours. Lidocaine mixtures may also be applied directly to the skin or mucous membranes to numb the area. It is often used mixed with a small amount of adrenaline (epinephrine) to prolong its local effects and to decrease bleeding.

Paresthesia is an abnormal sensation of the skin with no apparent physical cause. Paresthesia may be transient or chronic, and may have many possible underlying causes. Paresthesias are usually painless and can occur anywhere on the body, but most commonly occur in the arms and legs.

<span class="mw-page-title-main">Anesthetic</span> Drug that causes anesthesia

An anesthetic or anaesthetic is a drug used to induce anesthesia ⁠— ⁠in other words, to result in a temporary loss of sensation or awareness. They may be divided into two broad classes: general anesthetics, which result in a reversible loss of consciousness, and local anesthetics, which cause a reversible loss of sensation for a limited region of the body without necessarily affecting consciousness.

<span class="mw-page-title-main">Alveolar osteitis</span> Medical condition

Alveolar osteitis, also known as dry socket, is inflammation of the alveolar bone. Classically, this occurs as a postoperative complication of tooth extraction.

<span class="mw-page-title-main">Inferior alveolar nerve</span> Branch of the mandibular nerve

The inferior alveolar nerve(IAN) (also the inferior dental nerve) is a sensory branch of the mandibular nerve (CN V3) (which is itself the third branch of the trigeminal nerve (CN V)). The nerve provides sensory innervation to the lower/mandibular teeth and their corresponding gingiva as well as a small area of the face (via its mental nerve).

Infiltration analgesia is deposition of an analgesic drug close to the apex of a tooth so that it can diffuse to reach the nerve entering the apical foramina. It is the most routinely used in dental local treatment.

<span class="mw-page-title-main">Bupivacaine</span> Local anaesthetic drug

Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease feeling in a specific area. In nerve blocks, it is injected around a nerve that supplies the area, or into the spinal canal's epidural space. It is available mixed with a small amount of epinephrine to increase the duration of its action. It typically begins working within 15 minutes and lasts for 2 to 8 hours.

<span class="mw-page-title-main">Dental extraction</span> Operation to remove a tooth

A dental extraction is the removal of teeth from the dental alveolus (socket) in the alveolar bone. Extractions are performed for a wide variety of reasons, but most commonly to remove teeth which have become unrestorable through tooth decay, periodontal disease, or dental trauma, especially when they are associated with toothache. Sometimes impacted wisdom teeth cause recurrent infections of the gum (pericoronitis), and may be removed when other conservative treatments have failed. In orthodontics, if the teeth are crowded, healthy teeth may be extracted to create space so the rest of the teeth can be straightened.

<span class="mw-page-title-main">Nerve block</span> Deliberate inhibition of nerve impulses

Nerve block or regional nerve blockade is any deliberate interruption of signals traveling along a nerve, often for the purpose of pain relief. Local anesthetic nerve block is a short-term block, usually lasting hours or days, involving the injection of an anesthetic, a corticosteroid, and other agents onto or near a nerve. Neurolytic block, the deliberate temporary degeneration of nerve fibers through the application of chemicals, heat, or freezing, produces a block that may persist for weeks, months, or indefinitely. Neurectomy, the cutting through or removal of a nerve or a section of a nerve, usually produces a permanent block. Because neurectomy of a sensory nerve is often followed, months later, by the emergence of new, more intense pain, sensory nerve neurectomy is rarely performed.

<span class="mw-page-title-main">Phentolamine</span> An α-adrenergic antagonist medication

Phentolamine, sold under the brand name Regitine among others, is a reversible nonselective α-adrenergic antagonist.

<span class="mw-page-title-main">Prilocaine</span> Local anesthetic of the amino amide type

Prilocaine is a local anesthetic of the amino amide type first prepared by Claes Tegner and Nils Löfgren. In its injectable form, it is often used in dentistry. It is also often combined with lidocaine as a topical preparation for dermal anesthesia, for treatment of conditions like paresthesia. As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA).

<span class="mw-page-title-main">Chloroprocaine</span> Local anaesthetic drug

Chloroprocaine is a local anesthetic given by injection during surgical procedures and labor and delivery. Chloroprocaine vasodilates; this is in contrast to cocaine which vasoconstricts. Chloroprocaine is an ester anesthetic.

A retrobulbar block is a regional anesthetic nerve block in the retrobulbar space, the area located behind the globe of the eye. Injection of local anesthetic into this space constitutes the retrobulbar block. This injection provides akinesia of the extraocular muscles by blocking cranial nerves II, III, and VI, thereby preventing movement of the globe. Cranial nerve IV lies outside the muscle cone, and therefore is not affected by the local anesthesia. As a result, intorsion of the eye is still possible. It also provides sensory anesthesia of the conjunctiva, cornea and uvea by blocking the ciliary nerves. This block is most commonly employed for cataract surgery, but also provides anesthesia for other intraocular surgeries.

Dental anesthesia is the application of anesthesia to dentistry. It includes local anesthetics, sedation, and general anesthesia.

Topical tac is a topical anesthetic solution introduced by Pryor et al. in 1980. It is recommended for use on pediatric patients.

<span class="mw-page-title-main">Pterygomandibular space</span>

The pterygomandibular space is a fascial space of the head and neck. It is a potential space in the head and is paired on each side. It is located between the lateral pterygoid muscle and the medial surface of the ramus of the mandible. The pterygomandibular space is one of the four compartments of the masticator space.

References

  1. 1 2 Oertel R, Rahn R, Kirch W (December 1997). "Clinical pharmacokinetics of articaine". Clinical Pharmacokinetics. 33 (6): 417–425. doi:10.2165/00003088-199733060-00002. PMID   9435991. S2CID   38455660.
  2. 1 2 Oertel R, Ebert U, Rahn R, Kirch W. Clinical pharmacokinetics of articaine. Clin Pharmacokinet. 1997 Dec;33(6):418.
  3. ↑ Snoeck M (2012-06-05). "Articaine: a review of its use for local and regional anesthesia". Local and Regional Anesthesia. 5: 23–33. doi: 10.2147/LRA.S16682 . PMC   3417979 . PMID   22915899.
  4. 1 2 "Sanofi: 40 Jahre Ultracain in der Lokalanästhesie". zm-online (in German). 19 February 2016. Retrieved 2021-08-02.
  5. ↑ "O. Schmiedeberg-Plakette". dgpt-online.de. Archived from the original on 2021-08-02. Retrieved 2021-08-02.
  6. ↑ "Articain". roempp.thieme.de. Archived from the original on 2020-06-03. Retrieved 2021-08-02.
  7. 1 2 3 4 5 Malamed SF (2004). Handbook of Local Anaesthesia (5th ed.). St. Louis: Mosby. ISBN   978-0-323-02449-5.
  8. ↑ HornkeI, Eckert HG, Rupp W (1984). "Pharnakokinetik und Metabolismus von Articain nach intramuskularer Injektion am mannlichen Probanden". Dtsch Z Mund Kiefer Gesichts Chir. 8: 67–71.
  9. ↑ Kirch W, Kitteringham N, Lambers G, Hajdu P, Ohnhaus EE (September 1983). "Die klinische Pharmakokinetik von Articain nach intraoraler und intramuskulärer Applikation". Schweiz Monatsschr Zahnheilkd. 93 (9): 714–719.
  10. 1 2 Pogrel MA (April 2007). "Permanent nerve damage from inferior alveolar nerve blocks--an update to include articaine". Journal of the California Dental Association. 35 (4): 271–273. doi:10.1080/19424396.2007.12221225. PMID   17612365. S2CID   40570175.
  11. ↑ Segal MM, Rogers GF, Needleman HL, Chapman CA (December 2007). "Hypokalemic sensory overstimulation". Journal of Child Neurology. 22 (12): 1408–1410. doi:10.1177/0883073807307095. PMID   18174562. S2CID   35659227.
  12. ↑ Katyal V (April 2010). "The efficacy and safety of articaine versus lignocaine in dental treatments: a meta-analysis". Journal of Dentistry. 38 (4): 307–317. doi:10.1016/j.jdent.2009.12.003. PMID   20006669.
  13. ↑ Brandt RG, Anderson PF, McDonald NJ, Sohn W, Peters MC (May 2011). "The pulpal anesthetic efficacy of articaine versus lidocaine in dentistry: a meta-analysis". Journal of the American Dental Association. 142 (5): 493–504. doi:10.14219/jada.archive.2011.0219. PMID   21531931.
  14. ↑ Kung J, McDonagh M, Sedgley CM (November 2015). "Does Articaine Provide an Advantage over Lidocaine in Patients with Symptomatic Irreversible Pulpitis? A Systematic Review and Meta-analysis". Journal of Endodontics. 41 (11): 1784–1794. doi:10.1016/j.joen.2015.07.001. PMID   26293174.
  15. 1 2 Malamed SF (2013). Handbook of Local Anaesthesia (6th ed.). St. Louis: Mosby. p. 65.
  16. ↑ Becker DE, Reed KL (2006). "Essentials of local anesthetic pharmacology". Anesthesia Progress. 53 (3): 98–108, quiz 109–10. doi:10.2344/0003-3006(2006)53[98:EOLAP]2.0.CO;2. PMC   1693664 . PMID   17175824.
  17. ↑ Pogrel MA, Thamby S (July 2000). "Permanent nerve involvement resulting from inferior alveolar nerve blocks". Journal of the American Dental Association. 131 (7): 901–907. doi:10.14219/jada.archive.2000.0308. PMID   10916328.
  18. ↑ Haas DA, Lennon D (April 1995). "A 21 year retrospective study of reports of paresthesia following local anesthetic administration". Journal. 61 (4): 319–20, 323–6, 329–30. PMID   7736335.
  19. ↑ Haas DA, Lennon D (1996). "A review of local anesthetic-induced paraesthesia in Ontario in 1994". J Dent Res. 75 (Special Issue): 247.
  20. ↑ Miller PA, Haas DA (2000). "Incidence of local anesthetic-induced neuropathies in Ontario from 1994–1998". J Dent Res. 79 (Special Issue): 627.
  21. ↑ Haas DA, Lennon D (April 1995). "Local anesthetic use by dentists in Ontario". Journal (Canadian Dental Association). 61 (4): 297–304. PMID   7736333.
  22. ↑ Malamed SF (December 2006). "Local anesthetics: dentistry's most important drugs, clinical update 2006". Journal of the California Dental Association. 34 (12): 971–976. doi:10.1080/19424396.2006.12222270. PMID   17260521. S2CID   7863445.
  23. ↑ Hoffmeister B (December 1991). "[Morphological changes of peripheral nerves following intraneural injection of local anesthetic]". Deutsche Zahnarztliche Zeitschrift (in German). 46 (12): 828–830. PMID   1817900.

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