ARTICAINE HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H20N2O3S.ClH
Molecular Weight	320.835
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCCNC(C)C(=O)NC1=C(SC=C1C)C(=O)OC

InChI

InChIKey=GDWDBGSWGNEMGJ-UHFFFAOYSA-N

InChI=1S/C13H20N2O3S.ClH/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);1H

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020971s021lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19418088

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19418088	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020971s021lbl.pdf	Primary		Approved 8429	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 2000

C_max

Value	Dose	Co-administered	Analyte	Population
5.3 mg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9055188	600 mg 1 times / day steady-state, epidural dose: 600 mg route of administration: Epidural experiment type: STEADY-STATE co-administered: EPINEPHRINE	EPINEPHRINE	ARTICAINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
2037 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022466lbl.pdf	476 mg single, intraoral submucosal injection dose: 476 mg route of administration: Intraoral Submucosal Injection experiment type: SINGLE co-administered: EPINEPHRINE	EPINEPHRINE	ARTICAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
385 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022466lbl.pdf	68 mg single, dental dose: 68 mg route of administration: Dental experiment type: SINGLE co-administered: EPINEPHRINE	EPINEPHRINE	ARTICAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
900 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022466lbl.pdf	204 mg single, dental dose: 204 mg route of administration: Dental experiment type: SINGLE co-administered: EPINEPHRINE	EPINEPHRINE	ARTICAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
26.1 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9055188	600 mg 1 times / day steady-state, epidural dose: 600 mg route of administration: Epidural experiment type: STEADY-STATE co-administered: EPINEPHRINE	EPINEPHRINE	ARTICAINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9055188	600 mg 1 times / day steady-state, epidural dose: 600 mg route of administration: Epidural experiment type: STEADY-STATE co-administered: EPINEPHRINE	EPINEPHRINE	ARTICAINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
43.8 min DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022466lbl.pdf	476 mg single, intraoral submucosal injection dose: 476 mg route of administration: Intraoral Submucosal Injection experiment type: SINGLE co-administered: EPINEPHRINE	EPINEPHRINE	ARTICAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
30% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022466lbl.pdf			ARTICAINE serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/020971_SEPTOCAINE_MEDR_P1.PDF Page: 96001.02	unhealthy, 33.7 n = 159 Health Status: unhealthy Condition: pain Age Group: 33.7 Sex: M+F Population Size: 159 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/020971_SEPTOCAINE_MEDR_P1.PDF Page: 96001.02	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/020971_SEPTOCAINE_MEDR_P1.PDF Page: 96001.02

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 Nav1.7 36	UGT 192

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.7 36	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19418088/ Page: -	yes [IC50 8.8 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/7924890/ Page: -	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 192	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/201751Orig1s000lbl.pdf#page=2 Page: 2.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/16938156/ Page: -

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1095	http://www.3bsc.com/index/pro_info.php?id=54811
AA Blocks	AA00JGEF	https://www.aablocks.com/goods/Goods/detail?id=AA00JGEF
Alfa Chemistry	AP23964581	https://reagents.alfa-chemistry.com/product/articaine-cas-23964-58-1-8393.html
Alinda	ALBB-022443	http://alinda.ru/finechem_en_.html?i=ALBB-022443
Angene	AGN-PC-0WH438	http://www.angenechemical.com/productshow/AGN-PC-0WH438.html
Aronis	ARONIS25008	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=17901
Aurora Fine Chemicals LLC	A06.999.392	http://online.aurorafinechemicals.com/info?ID=A06.999.392
Aurora Fine Chemicals LLC	K06.990.023	http://online.aurorafinechemicals.com/info?ID=K06.990.023
Aurum Pharmatech LLC	T7555	http://www.Aurumpharmatech.com/Product/ProductDetails/T7555
BioSynth	Q-200652	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-200652.html
Boerchem	BC201427	http://www.boerchem.com/?product_33718.html
ChemMol	44000814	http://www.chemmol.com/chemmol/44000814.html
ChemMol	99052050	http://www.chemmol.com/chemmol/99052050.html
Chemspace	CSSB00000028440	https://chem-space.com/CSSB00000028440
Clearsynth	CS-T-04195	https://www.clearsynth.com/en/CST04195.html
Finetech	FT-0602880	http://www.finetechnology-ind.com/prod/detail/pub/23964-58-1.html
Hairui	HR126584	http://www.hairuichem.com/en/product/23964-58-1.html
LGC Standards	MM0369.11-0250	https://www.lgcstandards.com/US/en/p/MM0369.11-0250
Lab Network	LN01050165	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01050165
OChem	30659	http://www.ocheminc.com/index.php?act=psearch&pid=964A570
OChem	9332	http://www.ocheminc.com/index.php?act=psearch&pid=964A581
Oakwood	372965	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=144455&ExtHyperLink=1
Smolecule	S603454	https://www.smolecule.com/products/s603454
THE BioTek	bt-288825	https://www.thebiotek.com/product/others/bt-288825
Yuhao Chemical	RT15365	http://www.chemyuhao.com/23964-58-1.html
abcr GmbH	AB384620	http://www.abcr.com/shop/en/AB384620
iChemical	EBD8812	http://www.ichemical.com/chemicals/cas-23964-58-1
mcule	MCULE-1215719824	https://mcule.com/MCULE-1215719824/

PubMed

Title	Date	PubMed
Cardiovascular Parameters during Submaximal Exercise following Submucous Administration of Articaine : A Comparison with Lidocaine and Placebo in Young Healthy Volunteers.	2003	17535034
[Local anesthesia failure problems in conservative dental therapy clinic].	2006	17310940
Local anesthetics: dentistry's most important drugs, clinical update 2006.	2006 Dec	17260521
Is permanent maxillary tooth removal without palatal injection possible?	2006 Dec	17138173
Selection of local anesthetics in dentistry: clinical impression versus scientific assessment.	2006 Fall	17477214
The ethics of adopting a new drug: articaine as an example.	2006 Fall	17477213
Articaine and paresthesia: epidemiological studies.	2006 Fall	17477212
The anesthetic efficacy of 4 percent articaine 1:200,000 epinephrine: two controlled clinical trials.	2006 Nov	17082284
The pharmacokinetics and cardiovascular effects of high-dose articaine with 1:100,000 and 1:200,000 epinephrine.	2006 Nov	17082283
Permanent nerve damage from inferior alveolar nerve blocks--an update to include articaine.	2007 Apr	17612365
Articaine vs. lidocaine.	2007 Apr	17612363
The effect of food composition on serum testosterone levels after oral administration of Andriol Testocaps.	2007 Apr	17371478
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	17368327
The anesthetic efficacy of articaine in buccal infiltration of mandibular posterior teeth.	2007 Aug	17670879
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	18022467
Is articaine the hypoallergenic anesthetic?	2007 Feb	17300617
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	17274713
Articaine versus lidocaine: the author responds.	2007 Jun	17849965
[The influence of different local anaesthetics on the viability of preadipocytes].	2007 Jun	17602386
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	17322803
Articaine 4% with 1:200,000 epinephrine: an acceptable option for patients with long QT syndrome.	2007 May-Jun	17511356
More about articaine.	2007 Nov	17974631
Efficacy of articaine.	2007 Nov	17974629
Effects of articaine on action potential characteristics and the underlying ion currents in canine ventricular myocytes.	2007 Nov	17895236
Articaine: a new alternative in dental hygiene pain control.	2007 Summer	17908422
A prospective, randomized, double-blind comparison of articaine and lidocaine for maxillary infiltrations.	2008 Apr	18358883
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	18211939
Articaine interaction with DSPC bilayer: a 13C and 31P solid-state NMR study.	2008 Apr 23	18343644
[Feasibility of permanent maxillary tooth removal using articaine anesthesia without palatal injection].	2008 Aug	18780504
Efficacy of intraosseous injections of anesthetic in children and adolescents.	2008 Aug	18424118
Regional anesthesia techniques for ambulatory orthopedic surgery.	2008 Dec	19009687
Comparison of hyperbaric and plain articaine in spinal anaesthesia for open inguinal hernia repair.	2008 Dec	18922850
New Portland cement-based materials for endodontics mixed with articaine solution: a study of cellular response.	2008 Jan	18155489
An evaluation of buccal infiltrations and inferior alveolar nerve blocks in pulpal anesthesia for mandibular first molars.	2008 Jan	18155484
Spinal anaesthesia with articaine 5% vs bupivacaine 0.5% for day-case lower limb surgery: a double-blind randomized clinical trial.	2008 Jan	18070786
Analysis of the antimicrobial activity of local anaesthetics used for dental analgesia.	2008 Jan	18065672
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	18420431
Influence of local anesthethics with adrenalina 1:100.000 in basic vital constants during third molar surgery.	2008 Jul 1	18587307
A comparison of injection pain with articaine with adrenaline, prilocaine with phenylpressin and lidocaine with adrenaline.	2008 Jul 1	18587306
Anesthetic efficacy of the Gow-Gates injection and maxillary infiltration with articaine and lidocaine for irreversible pulpitis.	2008 Jun	18498883
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	18485309
Hemodynamic changes during the surgical removal of lower third molars.	2008 Mar	18280377
Articaine hydrochloride: a safe alternative to lignocaine?	2008 May	18557502
Articaine infiltration for anesthesia of mandibular first molars.	2008 May	18436027
Articaine use in children among dental practitioners.	2008 Nov-Dec	19186779
Effects of low-intensity pulsed ultrasound on dental implant osseointegration: a preliminary report.	2008 Oct	19212531
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	18762633
A comparison of the anesthetic efficacy of articaine and lidocaine in patients with irreversible pulpitis.	2009 Feb	19166765
Plain articaine or prilocaine for spinal anaesthesia in day-case knee arthroscopy: a double-blind randomized trial.	2009 Feb	19112061
Comparison of anesthetic efficacy of 4% articaine and 2% lidocaine for maxillary buccal infiltration in patients with irreversible pulpitis.	2009 Jan	19101495

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 HYDROCHLORIDE

Official Name

English

ARTICAINE HYDROCHLORIDE [USP IMPURITY]

Common Name

English

UBISTESINE

Brand Name

English

HOE-40045

Code

English

Methyl 4-methyl-3-[2-(propylamino)propionamido]-2-thiophenecarboxylate, monohydrochloride

Common Name

English

ARTICAINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

(±)-ARTICAINE HYDROCHLORIDE

Common Name

English

ARTICAINE HYDROCHLORIDE [MART.]

Common Name

English

ARTICAINE HYDROCHLORIDE [EP IMPURITY]

Common Name

English

ARTICAINE HYDROCHLORIDE [JAN]

Common Name

English

Articaine hydrochloride [WHO-DD]

Common Name

English

ARTICAINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

ARTICAINE HCL

Common Name

English

ULTRACAIN

Brand Name

English

ARTICAINE HYDROCHLORIDE [USP-RS]

Common Name

English

HOE-045

Code

English

ARTICAINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

SEPTANEST

Brand Name

English

2-THIOPHENECARBOXYLIC ACID, 4-METHYL-3-((1-OXO-2-(PROPYLAMINO)PROPYL)AMINO)-, METHYL ESTER, HYDROCHLORIDE (1:1)

Systematic Name

English

ARTICAINE HYDROCHLORIDE [USAN]

Common Name

English

METHYL 4-METHYL-3-(((2RS)-2-(PROPYLAMINO)PROPANOYL)AMINO)THIOPHENE-2-CARBOXYLATE HYDROCHLORIDE

Systematic Name

English

2-THIOPHENECARBOXYLIC ACID, 4-METHYL-3-((1-OXO-2-(PROPYLAMINO)PROPYL)AMINO)-, METHYL ESTER, MONOHYDROCHLORIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245