ETIDOCAINE

US Previously Marketed

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H28N2O
Molecular Weight	276.417
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN(CC)C(CC)C(=O)NC1=C(C)C=CC=C1C

InChI

InChIKey=VTUSIVBDOCDNHS-UHFFFAOYSA-N

InChI=1S/C17H28N2O/c1-6-12-19(8-3)15(7-2)17(20)18-16-13(4)10-9-11-14(16)5/h9-11,15H,6-8,12H2,1-5H3,(H,18,20)

HIDE SMILES / InChI

Description
Sources: http://www.rxlist.com/duranest-drug.htm
Curator's Comment: description was created based on several sources, including http://www.kiessig.com/drugs/druginfo.aspx?id=1218 | http://www.kiessig.com/drugs/druginfo.aspx?id=1218 | https://www.ncbi.nlm.nih.gov/pubmed/8799190 | https://www.ncbi.nlm.nih.gov/pubmed/8085162

Etidocaine, marketed under the trade name Duranest, is a local anesthetic given by injection during surgical procedures and labor and delivery. Etidocaine has a long duration of activity, and the main disadvantage of using during dentistry is increased bleeding during surgery. Etidocaine stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses, thereby effecting local anesthetic action.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel protein type II alpha subunit 27 Target ID: CHEMBL4187 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8085162	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.rxlist.com/duranest-drug/indications-dosage.htm#I	Primary		Approved 8429	DURANEST Approved Use INDICATIONS AND USAGE. Duranest (Etidocaine HCl) Injections are indicated for infiltration anesthesia, peripheral nerve blocks (e.g., brachial plexus, intercostal, retrobulbar, ulnar, inferior alveolar), and central neural block (i.e., lumbar or caudal epidural blocks). Launch Date 1976

C_max

Value	Dose	Co-administered	Analyte	Population
12.5 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/385208/	20 mL single, peridural dose: 20 mL route of administration: Peridural experiment type: SINGLE co-administered: EPINEPHRINE	EPINEPHRINE	ETIDOCAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1.8 μg × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/385208/	20 mL single, peridural dose: 20 mL route of administration: Peridural experiment type: SINGLE co-administered: EPINEPHRINE	EPINEPHRINE	ETIDOCAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.7 h REVIEW https://pubmed.ncbi.nlm.nih.gov/385208/	20 mL single, peridural dose: 20 mL route of administration: Peridural experiment type: SINGLE co-administered: EPINEPHRINE	EPINEPHRINE	ETIDOCAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% REVIEW https://pubmed.ncbi.nlm.nih.gov/385208/	20 mL single, peridural dose: 20 mL route of administration: Peridural experiment type: SINGLE co-administered: EPINEPHRINE	EPINEPHRINE	ETIDOCAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-031928	http://www.3bsc.com/index/pro_info.php?id=53192
AHH Chemical co.,ltd	MT-51699	http://www.ahhchemical.com/product/MT-51699.html
Alfa Chemistry	36637-18-0	https://www.alfa-chemistry.com/cas_36637-18-0.htm
Alsachim	2487	http://www.alsachim.com/product-C3557-glo.bal-view.html
Boerchem	BC686212	http://www.boerchem.com/?product_40319.html
ChemMol	44011515	http://www.chemmol.com/chemmol/44011515.html
ChemMol	49400382	http://www.chemmol.com/chemmol/49400382.html
Clearsynth	CS-O-11644	http://www.clearsynth.com/en/CSO11644.html
Clearsynth	CS-EK-02590	https://www.clearsynth.com/en/CSEK02590.html
Finetech	FT-0700005	http://www.finetechnology-ind.com/prod/detail/pub/36637-18-0.html
Parchem	87736	https://www.parchem.com/chemical-supplier-distributor/Etidocaine-087736.aspx
Smolecule	S580189	https://www.smolecule.com/products/s580189
THE BioTek	bt-298740	https://www.thebiotek.com/product/others/bt-298740
Yuhao Chemical	YH57290	http://www.chemyuhao.com/36637-18-0.html
iChemical	EBD25248	http://www.ichemical.com/chemicals/cas-36637-18-0

PubMed

Title	Date	PubMed
Etidocaine, bupivacaine, and lidocaine seizure thresholds in monkeys.	1975 Apr	1119714
A double-blind trial of bupivacaine (Marcain) and etidocaine (Duranest) in extradural block for surgical induction of labour.	1975 Dec	1218170
Relation of etidocaine and bupivacaine toxicity to rate of infusion in rhesus monkeys.	1977 Feb	402143
Central-nervous-system toxicity of local anesthetic mixtures in monkeys.	1977 Mar	402868
Comparative CNS toxicity of lidocaine, etidocaine, bupivacaine, and tetracaine in awake dogs following rapid intravenous administration.	1983 Apr	6829942
Comparison of pain associated with intradermal and subcutaneous infiltration with various local anesthetic solutions.	1987 Nov	3662064
Alterations in the pharmacokinetic properties of amide local anaesthetics following local anaesthetic induced convulsions.	1988 Oct	3188822
Local anesthetic-induced toxicity may be modified by low doses of flumazenil.	1992	1453872
Relative neural toxicity of local anesthetics.	1993 May	8492141
Pain of injection and duration of anesthesia for intradermal infiltration of lidocaine, bupivacaine, and etidocaine.	1994 Jul	8034840
Molecular determinants of state-dependent block of Na+ channels by local anesthetics.	1994 Sep 16	8085162
Toxic systemic reactions of bupivacaine and etidocaine.	1995 Jan	7614153
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001 Aug	11895133
Molecular determinants of voltage-dependent gating and binding of pore-blocking drugs in transmembrane segment IIIS6 of the Na(+) channel alpha subunit.	2001 Jan 5	11024055
Diffusive transport properties of some local anesthetics applicable for iontophoretic formulation of the drugs.	2001 May 7	11337149
Low-molecular-weight chiral cation exchangers: novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography.	2002 Feb	11870749
Spectrophotometric determination of etidocaine in pharmaceutical (dental) formulation.	2002 Jul 20	12093505
Cardiac toxicity of local anesthetics in the intact isolated heart model: a review.	2002 Nov-Dec	12430103
Local anesthesia: advances in agents and techniques.	2002 Oct	12436827
Peribulbar anaesthesia using a combination of lidocaine, bupivocaine and clonidine in vitreoretinal surgery.	2002 Sep	12355695
[Local anesthetics. Differences and similarities in the "-cains"].	2003 Apr	12715136
Toxicity of local anaesthetics.	2003 Mar	12751552
Differential effects of uncharged aminoamide local anesthetics on phospholipid bilayers, as monitored by 1H-NMR measurements.	2005 May 1	15848279
Lipid rescue resuscitation from local anaesthetic cardiac toxicity.	2006	17192120
[Retrobulbar anesthesia during keratolplasty].	2006 Feb	16755971
Liquid chromatography-electrospray mass spectrometry determination of free and total concentrations of ropivacaine in human plasma.	2006 Feb 2	16360344
Update on local anesthetics: focus on levobupivacaine.	2008 Apr	18728849
Cyclic metabolites: chemical and biological considerations.	2008 Feb	18288959
Preferential location of lidocaine and etidocaine in lecithin bilayers as determined by EPR, fluorescence and 2H NMR.	2008 Jan	17976897
Single injection peribulbar anesthesia with a short needle combined with digital compression.	2008 Nov	18931243
Complications and controversies of regional anaesthesia: a review.	2009 Oct	20640104
Direct vasocontractile activities of bupivacaine enantiomers on the isolated rat thoracic aorta.	2010	20981258
Use of local anaesthetics and adjuncts for spinal and epidural anaesthesia and analgesia at German and Austrian University Hospitals: an online survey to assess current standard practice.	2010 Apr 17	20398410
Advances in labor analgesia.	2010 Aug 9	21072284
Progress in analgesia for labor: focus on neuraxial blocks.	2010 Aug 9	21072273
Cardiogenic shock associated with loco-regional anesthesia rescued with left ventricular assist device implantation.	2010 Dec 8	21143858
The efficacy of ilioinguinal and iliohypogastric nerve block for postoperative pain after caesarean section.	2010 Jan	21526052
The effects of volatile induction and maintenance of anesthesia and selective spinal anesthesia on QT interval, QT dispersion, and arrhythmia incidence.	2010 Jun	20835552
Intravenous lipid emulsion in clinical toxicology.	2010 Oct 5	20923546
Anesthesia for cataract surgery: Recent trends.	2010 Sep	21120044
Circadian effects on neural blockade of intrathecal hyperbaric bupivacaine.	2010 Sep	20830264

Patents

Sample Use Guides

In Vivo Use Guide

The maximum dose to be employed as a single injection should be determined on the basis of the status of the patient and the type of regional anesthetic technique to be performed. Although single injections of 450 mg have been employed for regional anesthesia without adverse effects, at present it is strongly recommended that the maximal dose as a single injection should not exceed 400 mg (approximately 8.0 mg/kg or 3.6 mg/lb based on a 50 kg person) with epinephrine 1:200,000 and 300 mg (approximately 6 mg/kg or 2.7 mg/lb based on a 50 kg person) without epinephrine.

Route of Administration: Intramuscular

In Vitro Use Guide

Rat brain type IIA Na+ channels expressed in Xenopus oocytes were stimulated infrequently (1 pulse per 20 s, all currents were elicited by 15-ms pulses to 0 mV.) This tonic block mainly reflects drug binding to resting channels, the channel state that predominated at the holding potential of -90 mV. Etidocaine (200 mkM) decrease activities of WT Type IIA Na+ channels on ~40%.

Name

Type

Language

ETIDOCAINE

Official Name

English

W-19053 FREE BASE

Code

English

BUTANAMIDE, N-(2,6-DIMETHYLPHENYL)-2-(ETHYLPROPYLAMINO)-, (±)-

Common Name

English

ETIDOCAINE [USAN]

Common Name

English

(±)-2-(ETHYLPROPYLAMINO)-2',6'-BUTYROXYLIDIDE

Common Name

English

ETIDOCAINE [MI]

Common Name

English

2-(N-ETHYLPROPYLAMINO)-2',6'-BUTYROXYLIDIDE

Common Name

English

etidocaine [INN]

Common Name

English

ETIDOCAINE [MART.]

Common Name

English

Etidocaine [WHO-DD]

Common Name

English

BUTANAMIDE, N-(2,6-DIMETHYLPHENYL)-2-(ETHYLPROPYLAMINO)-

Systematic Name

English

ETIDOCAINE [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N01BB57