ETIDOCAINE HYDROCHLORIDE

US Previously Marketed

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H28N2O.ClH
Molecular Weight	312.878
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LMWQQUMMGGIGJQ-UHFFFAOYSA-N

InChI=1S/C17H28N2O.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C17H28N2O
Molecular Weight	276.417
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.rxlist.com/duranest-drug/indications-dosage.htm#I	Primary		Approved 8583	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-EK-02590	https://www.clearsynth.com/en/CSEK02590.html
Clearsynth	CS-O-11644	http://www.clearsynth.com/en/CSO11644.html
Finetech	FT-0700005	http://www.finetechnology-ind.com/prod/detail/pub/36637-18-0.html
iChemical	EBD25248	http://www.ichemical.com/chemicals/cas-36637-18-0
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

PubMed

Title	Date	PubMed
Cardiogenic shock associated with loco-regional anesthesia rescued with left ventricular assist device implantation.	2010-12-08	21143858
Intravenous lipid emulsion in clinical toxicology.	2010-10-05	20923546
Anesthesia for cataract surgery: Recent trends.	2010-09	21120044
Circadian effects on neural blockade of intrathecal hyperbaric bupivacaine.	2010-09	20830264
Advances in labor analgesia.	2010-08-09	21072284
Progress in analgesia for labor: focus on neuraxial blocks.	2010-08-09	21072273
The effects of volatile induction and maintenance of anesthesia and selective spinal anesthesia on QT interval, QT dispersion, and arrhythmia incidence.	2010-06	20835552
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.	2010-04-17	20398410
The efficacy of ilioinguinal and iliohypogastric nerve block for postoperative pain after caesarean section.	2010-01	21526052
Direct vasocontractile activities of bupivacaine enantiomers on the isolated rat thoracic aorta.	2010	20981258
Complications and controversies of regional anaesthesia: a review.	2009-10	20640104
Single injection peribulbar anesthesia with a short needle combined with digital compression.	2008-11	18931243
Update on local anesthetics: focus on levobupivacaine.	2008-04	18728849
Cyclic metabolites: chemical and biological considerations.	2008-02	18288959
Preferential location of lidocaine and etidocaine in lecithin bilayers as determined by EPR, fluorescence and 2H NMR.	2008-01	17976897
Liquid chromatography-electrospray mass spectrometry determination of free and total concentrations of ropivacaine in human plasma.	2006-02-02	16360344
[Retrobulbar anesthesia during keratolplasty].	2006-02	16755971
Lipid rescue resuscitation from local anaesthetic cardiac toxicity.	2006	17192120
Differential effects of uncharged aminoamide local anesthetics on phospholipid bilayers, as monitored by 1H-NMR measurements.	2005-05-01	15848279
[Local anesthetics. Differences and similarities in the "-cains"].	2003-04	12715136
Toxicity of local anaesthetics.	2003-03	12751552
Cardiac toxicity of local anesthetics in the intact isolated heart model: a review.	2002-11-14	12430103
Local anesthesia: advances in agents and techniques.	2002-10	12436827
Role of amino acid residues in transmembrane segments IS6 and IIS6 of the Na+ channel alpha subunit in voltage-dependent gating and drug block.	2002-09-20	12130650
Peribulbar anaesthesia using a combination of lidocaine, bupivocaine and clonidine in vitreoretinal surgery.	2002-09	12355695
Block of voltage-operated sodium channels by 2,6-dimethylphenol, a structural analogue of lidocaine's aromatic tail.	2002-09	12208786
Spectrophotometric determination of etidocaine in pharmaceutical (dental) formulation.	2002-07-20	12093505
Low-molecular-weight chiral cation exchangers: novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography.	2002-02	11870749
Benefit and risks of local anesthetics in infants and children.	2002	12269841
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001-08	11895133
Diffusive transport properties of some local anesthetics applicable for iontophoretic formulation of the drugs.	2001-05-07	11337149
Molecular determinants of voltage-dependent gating and binding of pore-blocking drugs in transmembrane segment IIIS6 of the Na(+) channel alpha subunit.	2001-01-05	11024055
Toxic systemic reactions of bupivacaine and etidocaine.	1995-01	7614153
Molecular determinants of state-dependent block of Na+ channels by local anesthetics.	1994-09-16	8085162
Pain of injection and duration of anesthesia for intradermal infiltration of lidocaine, bupivacaine, and etidocaine.	1994-07	8034840
Relative neural toxicity of local anesthetics.	1993-05	8492141
Local anesthetic-induced toxicity may be modified by low doses of flumazenil.	1992	1453872
Alterations in the pharmacokinetic properties of amide local anaesthetics following local anaesthetic induced convulsions.	1988-10	3188822
Comparison of pain associated with intradermal and subcutaneous infiltration with various local anesthetic solutions.	1987-11	3662064
Comparative CNS toxicity of lidocaine, etidocaine, bupivacaine, and tetracaine in awake dogs following rapid intravenous administration.	1983-04	6829942
Central-nervous-system toxicity of local anesthetic mixtures in monkeys.	1977-03	402868
Relation of etidocaine and bupivacaine toxicity to rate of infusion in rhesus monkeys.	1977-02	402143
A double-blind trial of bupivacaine (Marcain) and etidocaine (Duranest) in extradural block for surgical induction of labour.	1975-12	1218170
Etidocaine, bupivacaine, and lidocaine seizure thresholds in monkeys.	1975-04	1119714

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%.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:38 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:38 GMT 2025`
Record UNII	G6N3B3U8E6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DURANEST

Preferred Name

English

ETIDOCAINE HYDROCHLORIDE

Common Name

English

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

Common Name

English

ETIDOCAINE HYDROCHLORIDE [MI]

Common Name

English

W-19053

Code

English

DURANEST HYDROCHLORIDE

Common Name

English

ETIDOCAINE HYDROCHLORIDE [VANDF]

Common Name

English

ETIDOCAINE HYDROCHLORIDE [MART.]

Common Name

English

Etidocaine hydrochloride [WHO-DD]

Common Name

English

BUTANAMIDE, N-(2,6-DIMETHYLPHENYL)-2-(ETHYLPROPYLAMINO)-, HYDROCHLORIDE (1:1)

Systematic Name

English

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

Common Name

English

ETIDOCAINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

ETIDOCAINE HCL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245