Details
| Stereochemistry | UNKNOWN |
| Molecular Formula | C17H28N2O.ClH |
| Molecular Weight | 312.878 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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
| 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 | ( + / - ) |
| 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 |
DescriptionCurator'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
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4187 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | DURANEST Approved UseINDICATIONS 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 Date1976 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Title | Date | PubMed |
|---|---|---|
| Etidocaine, bupivacaine, and lidocaine seizure thresholds in monkeys. | 1975 Apr |
|
| Central-nervous-system toxicity of local anesthetic mixtures in monkeys. | 1977 Mar |
|
| Comparative CNS toxicity of lidocaine, etidocaine, bupivacaine, and tetracaine in awake dogs following rapid intravenous administration. | 1983 Apr |
|
| Local anesthetic-induced toxicity may be modified by low doses of flumazenil. | 1992 |
|
| Relative neural toxicity of local anesthetics. | 1993 May |
|
| Pain of injection and duration of anesthesia for intradermal infiltration of lidocaine, bupivacaine, and etidocaine. | 1994 Jul |
|
| Molecular determinants of state-dependent block of Na+ channels by local anesthetics. | 1994 Sep 16 |
|
| Toxic systemic reactions of bupivacaine and etidocaine. | 1995 Jan |
|
| Diffusive transport properties of some local anesthetics applicable for iontophoretic formulation of the drugs. | 2001 May 7 |
|
| Low-molecular-weight chiral cation exchangers: novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography. | 2002 Feb |
|
| Update on local anesthetics: focus on levobupivacaine. | 2008 Apr |
|
| Cyclic metabolites: chemical and biological considerations. | 2008 Feb |
|
| Single injection peribulbar anesthesia with a short needle combined with digital compression. | 2008 Nov |
|
| Complications and controversies of regional anaesthesia: a review. | 2009 Oct |
|
| Direct vasocontractile activities of bupivacaine enantiomers on the isolated rat thoracic aorta. | 2010 |
|
| 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 |
|
| Progress in analgesia for labor: focus on neuraxial blocks. | 2010 Aug 9 |
|
| Cardiogenic shock associated with loco-regional anesthesia rescued with left ventricular assist device implantation. | 2010 Dec 8 |
|
| The efficacy of ilioinguinal and iliohypogastric nerve block for postoperative pain after caesarean section. | 2010 Jan |
|
| Intravenous lipid emulsion in clinical toxicology. | 2010 Oct 5 |
|
| Anesthesia for cataract surgery: Recent trends. | 2010 Sep |
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
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
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Edited
Sat Dec 16 11:13:10 GMT 2023
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| Record UNII |
YGD0Y35434
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| Record Status |
Validated (UNII)
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| Record Version |
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YGD0Y35434
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1290125-23-3
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37498
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38188-14-6
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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RACEMATE -> ENANTIOMER |
