Page last updated: 2024-12-06

etidocaine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Etidocaine: A local anesthetic with rapid onset and long action, similar to BUPIVACAINE. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

etidocaine : An amino acid amide in which 2-[ethyl(propyl)amino]butanoic acid and 2,6-dimethylaniline have combined to form the amide bond. Used as a local anaesthetic (amide caine), it has rapid onset and long action properties, similar to bupivacaine, and is given by injection during surgical procedures and during labour and delivery. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID37497
CHEMBL ID492
CHEBI ID4904
SCHEMBL ID57261
MeSH IDM0007923

Synonyms (72)

Synonym
etidocaina
etidocainum
n-(2,6-dimethylphenyl)-2-(ethyl-propylamino)butanamide
gtpl2621
butanamide, n-(2,6-dimethylphenyl)-2-(ethylpropylamino)-, (.+/-.)-
n-(2,6-dimethylphenyl)-2-[ethyl(propyl)amino]butanamide
2',6'-butyroxylidide, 2-(ethylpropylamino)-
(+-)-n-(2,6-dimethylphenyl)-2-(ethylpropylamino)butanamide
w-19053
einecs 253-143-8
etidocainum [inn-latin]
duranest
(+-)-2-(ethylpropylamino)-2',6'-butyroxylidide
butanamide, n-(2,6-dimethylphenyl)-2-(ethylpropylamino)-, (+-)-
2-(ethylpropylamino)-2',6'-butyroxylidide
etidocaina [inn-spanish]
brn 2741181
etidocaine (usan/inn)
D04095
36637-18-0
C07530
etidocaine
w-19053 [as hydrochloride]
CHEMBL492
chebi:4904 ,
tox21_112968
dtxsid1023027 ,
cas-36637-18-0
dtxcid703027
unii-i6cqm0f31v
etidocaine [usan:inn:ban]
i6cqm0f31v ,
60108-68-1
butanamide, n-(2,6-dimethylphenyl)-2-(ethylpropylamino)-, (+/-)-
etidocaine [usan]
etidocaine [vandf]
etidocaine [mart.]
2-(n-ethylpropylamino)-2',6'-butyroxylidide
(+/-)-2-(ethylpropylamino)-2',6'-butyroxylidide
etidocaine [mi]
etidocaine [who-dd]
butanamide, n-(2,6-dimethylphenyl)-2-(ethylpropylamino)-
w-19053 free base
etidocaine [inn]
SCHEMBL57261
etidocaine, (+)-
unii-y83xvy9aq8
y83xvy9aq8 ,
unii-k9d2ce52pu
38188-41-9
k9d2ce52pu ,
butanamide, n-(2,6-dimethylphenyl)-2-(ethylpropylamino)-, (-)-
butanamide, n-(2,6-dimethylphenyl)-2-(ethylpropylamino)-, (+)-
etidocaine, (-)-
38188-42-0
VTUSIVBDOCDNHS-UHFFFAOYSA-N
(.+/-.)-2-(ethylpropylamino)-2',6'-butyroxylidide
n-(2,6-dimethylphenyl)-2-(ethylpropylamino)butanamide
DB08987
levo-etidocaine
(-)-etidocaine
dextro-etidocaine
(+)-etidocaine
n-(2,6-dimethylphenyl)-2-(ethyl(propyl)amino)butanamide
FT-0700005
Q304782
duranest [as hydrochloride]
bdbm50225497
EN300-17956322
CS-0017487
HY-B2080
AKOS040751744

Research Excerpts

Overview

Etidocaine is a long lasting local anesthetic, which alleged toxicity has restricted its clinical use. Etidocane 0.5% acts as a vasodilator at the site of injection.

ExcerptReferenceRelevance
"Etidocaine (EDC) is a long lasting local anesthetic, which alleged toxicity has restricted its clinical use. "( Sustained Release from Ionic-Gradient Liposomes Significantly Decreases ETIDOCAINE Cytotoxicity.
Casadei, BR; Couto, VM; de Paula, E; Martinez, EF; Oliveira, JD; Ribeiro, LNM; Rodrigues da Silva, GH, 2018
)
2.16
"3. Etidocaine 0.5% acts as a vasodilator at the site of injection."( Intercostal blocks with etidocaine. Preliminary report.
Dhunér, KG; Lund, N, 1975
)
1.08

Effects

Etidocaine 1 per cent has been compared with lidocaine 2 per cent for epidural anaesthesia for surgery. It has less pronounced effects on the cardiovascular system, but may be associated with inadequate control of intraoperative bleeding.

ExcerptReferenceRelevance
"Etidocaine 1 per cent has been compared with lidocaine 2 per cent for epidural anaesthesia for surgery. "( A comparison of etidocaine and lidocaine in epidural analgesia for surgery.
Edelist, G; Raksamani, A, 1977
)
2.05
"Etidocaine has been evaluated in extradural block with regard to its absorption, toxicity and clinical effectiveness, which have been compared with those of bupivacaine. "( Evaluation of etidocaine in extradural block.
Abdel-Salam, AR; Scott, DB; Vonwiller, JB, 1975
)
2.06
"Etidocaine has less pronounced effects on the cardiovascular system, but its use may be associated with inadequate control of intraoperative bleeding."( Long-acting local anesthetics in dentistry.
Sisk, AL, 1992
)
1

Toxicity

ExcerptReferenceRelevance
" The pharmacokinetics of these compounds are discussed in this review, with particular emphasis on the fetal exposure and its relationship to adverse effects on the fetus."( Clinical pharmacokinetics in pregnancy and perinatology. I. Placental transfer and fetal side effects of local anaesthetic agents.
Nau, H, 1985
)
0.27
" These results suggest that the CNS is the primary target organ for the toxic effects of both highly lipid-soluble and highly protein-bound local anesthetics (i."( Comparative CNS toxicity of lidocaine, etidocaine, bupivacaine, and tetracaine in awake dogs following rapid intravenous administration.
Covino, BG; Feldman, HS; Giasi, R; Liu, PL; Patterson, MK, 1983
)
0.54
" In contrast, no significant difference in etidocaine blood concentrations at the onset of each toxic symptom was observed among the groups except that convulsions and hypotension occurred at lower blood levels in the fetus as compared with the newborn and adult."( Etidocaine toxicity in the adult, newborn, and fetal sheep.
Covino, BG; Feldman, HS; Finster, M; Morishima, HO; Pedersen, H, 1983
)
1.97
" Future areas of investigation will focus on improved treatment regimes and better understanding of the mechanism of lipid rescue, which might allow superior alternative therapies, or treatment of other toxic events."( Lipid rescue resuscitation from local anaesthetic cardiac toxicity.
Weinberg, G, 2006
)
0.33

Pharmacokinetics

The comparative pharmacokinetic properties were investigated in convulsing and non-convulsing dogs. Mean half-life of elimination of etidocaine calculated from sigma-minus plots of the neonatal urinary data was 6.

ExcerptReferenceRelevance
" The method is accurate, fast and sensitive and has been applied in a pharmacokinetic study of bupivacaine."( The use of a packed column for the determination of bupivacaine in human plasma by gas chromatography: an application in a pharmacokinetic study of bupivacaine.
Chan, K; Lau, OW; Wong, YC, 1992
)
0.28
" However, the limiting dosages determined up to now do not take account of important pharmacokinetic and toxicological data: (1) The dependence of blood levels measured on the technique of regional anesthesia and (2) the raised toxicity of a local anesthetic solution containing adrenaline following inadvertent intravascular (intravenous) injection."( [Dose limits for local anesthetics. Recommendations based on toxicologic and pharmacokinetic data].
Kaiser, H; Niesel, HC, 1991
)
0.28
"The comparative pharmacokinetic properties of lidocaine, bupivacaine, etidocaine and mepivacaine were investigated in convulsing and non-convulsing dogs."( Alterations in the pharmacokinetic properties of amide local anaesthetics following local anaesthetic induced convulsions.
Arthur, GR; Covino, BG; Feldman, HS, 1988
)
0.51

Bioavailability

ExcerptReferenceRelevance
" It is concluded that the addition of adrenaline reduces the fraction of the dose being absorbed during the first (fast) phase rather than influencing the absorption rate constants."( The effects of adding adrenaline to etidocaine and lignocaine in extradural anaesthesia II: Pharmacokinetics.
Bonica, JJ; Mather, LE; Murphy, TM; Tucker, GT, 1976
)
0.53
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

min-1 decreased the seizure dosage of etidocaine but had no effect on that of bupivacaine.

ExcerptRelevanceReference
"min-1 decreased the seizure dosage of etidocaine but had no effect on that of bupivacaine."( Relation of etidocaine and bupivacaine toxicity to rate of infusion in rhesus monkeys.
Embro, WJ; Malagodi, MH; Munson, ES, 1977
)
0.91
" The need for limiting the dosage of local anesthetic agents is stressed."( [New aspects of field blocks and peripheral nerve blocks (author's transl)].
Schulte-Steinberg, O, 1977
)
0.26
"The physical status of the patient (sex, age, weight, height, and underlying disease) has been thought to influence the dosage of local anesthetic drugs that can be injected without causing a systemic toxic reaction, but this belief is not supported by statistically significant data."( Factors determining dosages of amide-type local anesthetic drugs.
Balfour, RI; Bridenbaugh, LD; Horton, WG; Moore, DC; Thompson, GE, 1977
)
0.26
" Diluted etidocaine solutions seem to be adequate: irrespective the technique used for eliminating the reflex, diluted etidocaine produces a good effect and permits a dosage reduction compared with other local anesthetics."( [Elimination of the obturator reflex as a specific indication for dilute solutions of etidocaine. A study of the suitability of a local anesthetic for reflex elimination in the 3-in-1 block technic].
Kissler, GV; Reinhold, P; Schwilick, R; Weingärtner, K, 1990
)
0.92
" This method can be applied to injectable pharmaceutical preparation dosage studied."( Spectrophotometric determination of etidocaine in pharmaceutical (dental) formulation.
Schapoval, EE; Silva, N, 2002
)
0.59
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
local anaestheticAny member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
amino acid amideAn amide of an amino acid formed formally by conversion of the carboxy group to a carboxamido group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Potassium channel subfamily K member 3Homo sapiens (human)IC50 (µMol)39.00000.00700.89855.1000AID1525553
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
potassium ion transportPotassium channel subfamily K member 3Homo sapiens (human)
chemical synaptic transmissionPotassium channel subfamily K member 3Homo sapiens (human)
response to xenobiotic stimulusPotassium channel subfamily K member 3Homo sapiens (human)
monoatomic ion transmembrane transportPotassium channel subfamily K member 3Homo sapiens (human)
negative regulation of cytosolic calcium ion concentrationPotassium channel subfamily K member 3Homo sapiens (human)
regulation of resting membrane potentialPotassium channel subfamily K member 3Homo sapiens (human)
cellular response to zinc ionPotassium channel subfamily K member 3Homo sapiens (human)
cellular response to hypoxiaPotassium channel subfamily K member 3Homo sapiens (human)
cochlea developmentPotassium channel subfamily K member 3Homo sapiens (human)
potassium ion transmembrane transportPotassium channel subfamily K member 3Homo sapiens (human)
stabilization of membrane potentialPotassium channel subfamily K member 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
monoatomic ion channel activityPotassium channel subfamily K member 3Homo sapiens (human)
open rectifier potassium channel activityPotassium channel subfamily K member 3Homo sapiens (human)
potassium channel activityPotassium channel subfamily K member 3Homo sapiens (human)
potassium ion leak channel activityPotassium channel subfamily K member 3Homo sapiens (human)
S100 protein bindingPotassium channel subfamily K member 3Homo sapiens (human)
outward rectifier potassium channel activityPotassium channel subfamily K member 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membranePotassium channel subfamily K member 3Homo sapiens (human)
synapsePotassium channel subfamily K member 3Homo sapiens (human)
plasma membranePotassium channel subfamily K member 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID450273Lipophilicity, log P of the compound2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Ligand-based design and synthesis of novel sodium channel blockers from a combined phenytoin-lidocaine pharmacophore.
AID205267Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex1985Journal of medicinal chemistry, Mar, Volume: 28, Issue:3
[3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.
AID205268Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM1985Journal of medicinal chemistry, Mar, Volume: 28, Issue:3
[3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1525553Inhibition of human TASK1 expressed in Xenopus oocytes by whole cell voltage clamp assay2019Journal of medicinal chemistry, 11-27, Volume: 62, Issue:22
TASK Channels Pharmacology: New Challenges in Drug Design.
AID27367Lethal dose of compound evaluated by administering intraperitoneally to female CRCD mice1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
New antiarrhythmic agents. 7. 2,3-Diaminopropionanilides.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID174466Anesthetic activity of compound (0.125%) was evaluated by duration of sciatic nerve block1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
New antiarrhythmic agents. 7. 2,3-Diaminopropionanilides.
AID174598Anesthetic activity of compound (0.5%) was evaluated by duration of sciatic nerve block1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
New antiarrhythmic agents. 7. 2,3-Diaminopropionanilides.
AID27368Lethal dose of compound evaluated by administering intravenously to female CRCD mice1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
New antiarrhythmic agents. 7. 2,3-Diaminopropionanilides.
AID450269Displacement of [3H]-BTX-B from neuronal voltage-gated sodium channel in rat cerebral cortex synaptoneurosomes2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Ligand-based design and synthesis of novel sodium channel blockers from a combined phenytoin-lidocaine pharmacophore.
AID1061889Displacement of [3H]BTX-B from neuronal voltage-gated sodium channel in rat cerebral cortex synaptoneurosomes after 60 mins by scintillation counting2014Bioorganic & medicinal chemistry, Jan-01, Volume: 22, Issue:1
A highly predictive 3D-QSAR model for binding to the voltage-gated sodium channel: design of potent new ligands.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID174596Anesthetic activity of compound (0.25%) was evaluated by duration of sciatic nerve block1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
New antiarrhythmic agents. 7. 2,3-Diaminopropionanilides.
AID1346731Rat Nav1.2 (Voltage-gated sodium channels)1994Science (New York, N.Y.), Sep-16, Volume: 265, Issue:5179
Molecular determinants of state-dependent block of Na+ channels by local anesthetics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (273)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990199 (72.89)18.7374
1990's53 (19.41)18.2507
2000's15 (5.49)29.6817
2010's4 (1.47)24.3611
2020's2 (0.73)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.65

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index36.65 (24.57)
Research Supply Index5.95 (2.92)
Research Growth Index3.98 (4.65)
Search Engine Demand Index54.73 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials85 (28.52%)5.53%
Reviews18 (6.04%)6.00%
Case Studies7 (2.35%)4.05%
Observational0 (0.00%)0.25%
Other188 (63.09%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]