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Details

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

SHOW SMILES / InChI
Structure of ETIDOCAINE, (-)-

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

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
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

Curator's Comment: http://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC2163529&blobtype=pdf

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
12.5 μg/mL
20 mL single, peridural
dose: 20 mL
route of administration: Peridural
experiment type: SINGLE
co-administered: EPINEPHRINE
ETIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.8 μg × h/mL
20 mL single, peridural
dose: 20 mL
route of administration: Peridural
experiment type: SINGLE
co-administered: EPINEPHRINE
ETIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.7 h
20 mL single, peridural
dose: 20 mL
route of administration: Peridural
experiment type: SINGLE
co-administered: EPINEPHRINE
ETIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
20 mL single, peridural
dose: 20 mL
route of administration: Peridural
experiment type: SINGLE
co-administered: EPINEPHRINE
ETIDOCAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Toxic systemic reactions of bupivacaine and etidocaine.
1995 Jan
Benefit and risks of local anesthetics in infants and children.
2002
Block of voltage-operated sodium channels by 2,6-dimethylphenol, a structural analogue of lidocaine's aromatic tail.
2002 Sep
Complications and controversies of regional anaesthesia: a review.
2009 Oct
Direct vasocontractile activities of bupivacaine enantiomers on the isolated rat thoracic aorta.
2010
The effects of volatile induction and maintenance of anesthesia and selective spinal anesthesia on QT interval, QT dispersion, and arrhythmia incidence.
2010 Jun
Intravenous lipid emulsion in clinical toxicology.
2010 Oct 5
Circadian effects on neural blockade of intrathecal hyperbaric bupivacaine.
2010 Sep
Patents

Patents

Sample Use Guides

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 Sat Dec 16 11:13:09 GMT 2023
Edited
by admin
on Sat Dec 16 11:13:09 GMT 2023
Record UNII
K9D2CE52PU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETIDOCAINE, (-)-
Common Name English
(-)-ETIDOCAINE
Common Name English
BUTANAMIDE, N-(2,6-DIMETHYLPHENYL)-2-(ETHYLPROPYLAMINO)-, (-)-
Systematic Name English
LEVO-ETIDOCAINE
Common Name English
Code System Code Type Description
FDA UNII
K9D2CE52PU
Created by admin on Sat Dec 16 11:13:09 GMT 2023 , Edited by admin on Sat Dec 16 11:13:09 GMT 2023
PRIMARY
CAS
38188-41-9
Created by admin on Sat Dec 16 11:13:09 GMT 2023 , Edited by admin on Sat Dec 16 11:13:09 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER