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Details

Stereochemistry RACEMIC
Molecular Formula C13H20N2O3S
Molecular Weight 284.3761
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTICAINE

SMILES

CCCNC(C)C(=Nc1c(C)csc1C(=O)OC)O

InChI

InChIKey=QTGIAADRBBLJGA-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Articaine is a dental local anesthetic, which is the most widely used in a number of European countries and is available in many countries around the world. Articaine in combination with epinephrine under the brand name Septocaine is indicated for local, infiltrative, or conductive anesthesia in both simple and complex dental procedures. Local anesthetics block the generation and conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rising of the action potential. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of the affected nerve fibers. Articaine blocks the actions on Na+ channels. Epinephrine is a vasoconstrictor added to articaine HCl to slow absorption into the general circulation and thus prolong maintenance of an active tissue concentration.

Originator

Curator's Comment:: Articaine HC1 was synthesized by Rusching et al. in 1969 and was first marketed in Germany in 1969 with the name Carticaine

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SEPTOCAINE

Approved Use

Articaine HCl and Epinephrine, an amide local anesthetic containing a vasoconstrictor, is indicated for local, infiltrative, or conductive anesthesia in both simple and complex dental procedures. Articaine HCl and Epinephrine, an amide local anesthetic containing a vasoconstrictor, is indicated for local, infiltrative, or conductive anesthesia in both simple and complex dental procedures.

Launch Date

9.5471999E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.3 mg/mL
600 mg 1 times / day steady-state, epidural
dose: 600 mg
route of administration: Epidural
experiment type: STEADY-STATE
co-administered: EPINEPHRINE
ARTICAINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2037 ng/mL
476 mg single, intraoral submucosal injection
dose: 476 mg
route of administration: Intraoral Submucosal Injection
experiment type: SINGLE
co-administered: EPINEPHRINE
ARTICAINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
385 ng/mL
68 mg single, dental
dose: 68 mg
route of administration: Dental
experiment type: SINGLE
co-administered: EPINEPHRINE
ARTICAINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
900 ng/mL
204 mg single, dental
dose: 204 mg
route of administration: Dental
experiment type: SINGLE
co-administered: EPINEPHRINE
ARTICAINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
26.1 μM × h
600 mg 1 times / day steady-state, epidural
dose: 600 mg
route of administration: Epidural
experiment type: STEADY-STATE
co-administered: EPINEPHRINE
ARTICAINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.19 h
600 mg 1 times / day steady-state, epidural
dose: 600 mg
route of administration: Epidural
experiment type: STEADY-STATE
co-administered: EPINEPHRINE
ARTICAINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
43.8 min
476 mg single, intraoral submucosal injection
dose: 476 mg
route of administration: Intraoral Submucosal Injection
experiment type: SINGLE
co-administered: EPINEPHRINE
ARTICAINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
ARTICAINE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
7 mg/kg 1 times / day single, supraperiosteal injection
Recommended
Dose: 7 mg/kg, 1 times / day
Route: supraperiosteal injection
Route: single
Dose: 7 mg/kg, 1 times / day
Sources: Page: 96001.02
unhealthy, 33.7
n = 159
Health Status: unhealthy
Condition: pain
Age Group: 33.7
Sex: M+F
Population Size: 159
Sources: Page: 96001.02
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 8.8 uM]
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cardiovascular Parameters during Submaximal Exercise following Submucous Administration of Articaine : A Comparison with Lidocaine and Placebo in Young Healthy Volunteers.
2003
[Local anesthesia failure problems in conservative dental therapy clinic].
2006
Local anesthetics: dentistry's most important drugs, clinical update 2006.
2006 Dec
Is permanent maxillary tooth removal without palatal injection possible?
2006 Dec
Selection of local anesthetics in dentistry: clinical impression versus scientific assessment.
2006 Fall
The ethics of adopting a new drug: articaine as an example.
2006 Fall
Articaine and paresthesia: epidemiological studies.
2006 Fall
The anesthetic efficacy of 4 percent articaine 1:200,000 epinephrine: two controlled clinical trials.
2006 Nov
The pharmacokinetics and cardiovascular effects of high-dose articaine with 1:100,000 and 1:200,000 epinephrine.
2006 Nov
Permanent nerve damage from inferior alveolar nerve blocks--an update to include articaine.
2007 Apr
Articaine vs. lidocaine.
2007 Apr
The effect of food composition on serum testosterone levels after oral administration of Andriol Testocaps.
2007 Apr
Comparison of 4% articaine with 1:100,000 epinephrine and 2% lidocaine with 1:100,000 epinephrine when used as a supplemental anesthetic.
2007 Apr
The anesthetic efficacy of articaine in buccal infiltration of mandibular posterior teeth.
2007 Aug
Epinephrine concentration (1:100,000 or 1:200,000) does not affect the clinical efficacy of 4% articaine for lower third molar removal: a double-blind, randomized, crossover study.
2007 Dec
Is articaine the hypoallergenic anesthetic?
2007 Feb
Hemostatic and anesthetic efficacy of 4% articaine HCl with 1:200,000 epinephrine and 4% articaine HCl with 1:100,000 epinephrine when administered intraorally for periodontal surgery.
2007 Feb
Articaine versus lidocaine: the author responds.
2007 Jun
[The influence of different local anaesthetics on the viability of preadipocytes].
2007 Jun
Comparative study of the anesthetic efficacy of 4% articaine versus 2% lidocaine in inferior alveolar nerve block during surgical extraction of impacted lower third molars.
2007 Mar 1
Articaine 4% with 1:200,000 epinephrine: an acceptable option for patients with long QT syndrome.
2007 May-Jun
More about articaine.
2007 Nov
Efficacy of articaine.
2007 Nov
Effects of articaine on action potential characteristics and the underlying ion currents in canine ventricular myocytes.
2007 Nov
Articaine: a new alternative in dental hygiene pain control.
2007 Summer
A prospective, randomized, double-blind comparison of articaine and lidocaine for maxillary infiltrations.
2008 Apr
Comparison of 4% articaine and 0.5% levobupivacaine/2% lidocaine mixture for sub-Tenon's anaesthesia in phacoemulsification cataract surgery: a randomised controlled trial.
2008 Apr
Articaine interaction with DSPC bilayer: a 13C and 31P solid-state NMR study.
2008 Apr 23
[Feasibility of permanent maxillary tooth removal using articaine anesthesia without palatal injection].
2008 Aug
Efficacy of intraosseous injections of anesthetic in children and adolescents.
2008 Aug
Regional anesthesia techniques for ambulatory orthopedic surgery.
2008 Dec
Comparison of hyperbaric and plain articaine in spinal anaesthesia for open inguinal hernia repair.
2008 Dec
New Portland cement-based materials for endodontics mixed with articaine solution: a study of cellular response.
2008 Jan
An evaluation of buccal infiltrations and inferior alveolar nerve blocks in pulpal anesthesia for mandibular first molars.
2008 Jan
Spinal anaesthesia with articaine 5% vs bupivacaine 0.5% for day-case lower limb surgery: a double-blind randomized clinical trial.
2008 Jan
Analysis of the antimicrobial activity of local anaesthetics used for dental analgesia.
2008 Jan
A comparison of the clinical anesthetic efficacy of 4% articaine and 0.5% bupivacaine (both with 1:200,000 epinephrine) for lower third molar removal.
2008 Jul
Influence of local anesthethics with adrenalina 1:100.000 in basic vital constants during third molar surgery.
2008 Jul 1
A comparison of injection pain with articaine with adrenaline, prilocaine with phenylpressin and lidocaine with adrenaline.
2008 Jul 1
Anesthetic efficacy of the Gow-Gates injection and maxillary infiltration with articaine and lidocaine for irreversible pulpitis.
2008 Jun
The cardiovascular effect of local anesthesia with articaine plus 1:200,000 adrenalin versus lidocaine plus 1:100,000 adrenalin in medically compromised cardiac patients: a prospective, randomized, double blinded study.
2008 Jun
Hemodynamic changes during the surgical removal of lower third molars.
2008 Mar
Articaine hydrochloride: a safe alternative to lignocaine?
2008 May
Articaine infiltration for anesthesia of mandibular first molars.
2008 May
Articaine use in children among dental practitioners.
2008 Nov-Dec
Effects of low-intensity pulsed ultrasound on dental implant osseointegration: a preliminary report.
2008 Oct
Comparing anesthetic efficacy of articaine versus lidocaine as a supplemental buccal infiltration of the mandibular first molar after an inferior alveolar nerve block.
2008 Sep
A comparison of the anesthetic efficacy of articaine and lidocaine in patients with irreversible pulpitis.
2009 Feb
Plain articaine or prilocaine for spinal anaesthesia in day-case knee arthroscopy: a double-blind randomized trial.
2009 Feb
Comparison of anesthetic efficacy of 4% articaine and 2% lidocaine for maxillary buccal infiltration in patients with irreversible pulpitis.
2009 Jan

Sample Use Guides

For dental injection by submucosal infiltration or nerve block. For infiltration: 0.5-2.5 mL (20-100 mg articaine HCl). For nerve block: 0.5-3.4 mL (20-136 mg articaine HCl). For oral surgery: 1.0-5.1 mL (40-204 mg articaine HCl). Maximum recommended dosages: Adults: 7 mg/kg (0.175 mL/kg); Children 4-16 years: 7 mg/kg (0.175 mL/kg), depending on the age, weight and magnitude of the operation.
Route of Administration: Other
It was investigated the ability of local anaesthetics to inhibit reactive oxygen and nitrogen species generated by either stimulated human leucocytes or cell-free systems using luminol chemiluminescence (CL). Prilocaine inhibited formyl-methionyl-leucyl-phenylalanine (FMLP) - induced CL in leucocytes (94+/-1%, at 1 mM), whereas articaine showed an activation (59+/-7%) at high concentration (1 mM) and inhibition (13+/-6%) at low concentration (0.1 mM). In cell-free experiments, prilocaine (22+/-6%, at 1 mM) and articaine (85+/-1%, at 1 mM) caused concentration-dependent inhibition in xanthine-xanthine oxidase-induced CL. Although articaine had no effect on H2O2-induced CL, prilocaine significantly attenuated the H2O2 signal (97+/-0.3%, at 1 mM). Prilocaine (99+/-0.04%, 1 mM) and articaine (70+/-6%, 1 mM) markedly inhibited HOCl-induced CL, whereas these drugs had no effect on FeSO4-induced CL. Articaine inhibited peroxynitrite CL (63+/-6%, 1 mM), but prilocaine did not produce any depression on this signal.
Name Type Language
ARTICAINE
INN   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
HOE 045
Code English
40-045
Code English
ARTICAINE [USP-RS]
Common Name English
2-THIOPHENECARBOXYLIC ACID, 4-METHYL-3-((1-OXO-2-(PROPYLAMINO)PROPYL)AMINO)-, METHYL ESTER
Common Name English
METHYL 4-METHYL-3-(2-(PROPYLAMINO)PROPIONAMIDO)-2-THIOPHENECARBOXYLATE
Systematic Name English
ARTICAINE [INN]
Common Name English
ARTICAINE [WHO-DD]
Common Name English
CARTICAINE
MI  
Common Name English
SEPTOCAINE
Brand Name English
CARTICAINE [MI]
Common Name English
40 045
Code English
ARTICAINE [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175682
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
WHO-VATC QN01BB08
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
NDF-RT N0000175976
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
NDF-RT N0000007681
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
NCI_THESAURUS C245
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
WHO-ATC N01BB58
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
WHO-ATC N01BB08
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
WHO-VATC QN01BB58
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
Code System Code Type Description
LACTMED
Articaine
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
PUBCHEM
32170
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
DRUG BANK
DB09009
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
MERCK INDEX
M3139
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1093
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
WIKIPEDIA
ARTICAINE
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
CAS
23964-58-1
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
EPA CompTox
23964-58-1
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
INN
3193
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
FDA UNII
D3SQ406G9X
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
NCI_THESAURUS
C72173
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
USP_CATALOG
1042907
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY USP-RS
RXCUI
592464
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY RxNorm
MESH
D002355
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
EVMPD
SUB05577MIG
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY
DRUG CENTRAL
3070
Created by admin on Sat Jun 26 04:41:12 UTC 2021 , Edited by admin on Sat Jun 26 04:41:12 UTC 2021
PRIMARY