Etidocaine

Etidocaine, marketed under the trade name Duranest, is an amide-type 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.[1]

Etidocaine
Clinical data
Trade namesDuranest
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa603026
Pregnancy
category
  • AU: B1
Routes of
administration		Parenteral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a
MetabolismHepatic
Elimination half-life2.5 hours
ExcretionRenal
Identifiers
IUPAC name
  • N-(2,6-dimethylphenyl)-
    2-(ethyl(propyl)amino)butanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.296
Chemical and physical data
FormulaC17H28N2O
Molar mass276.424 g·mol−1
3D model (JSmol)
SMILES
  • O=C(Nc1c(C)cccc1C)C(CC)N(CC)CCC
InChI
  • 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) Y
  • Key:VTUSIVBDOCDNHS-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis
Patent:[2] 2-bromobutyryl chloride synthesis:[3]

The amide reaction between 2,6-xylidine (1) and 2-bromobutyryl chloride [22118-12-3] (2) gives 2-Bromo-N-(2,6-Dimethylphenyl)Butanamide [53984-81-9] (3). Alkylation with N-Ethylpropylamine [20193-20-8] (4) gives Etidocaine (5).

References
  1. Sisk AL (1992). "Long-acting local anesthetics in dentistry". Anesthesia Progress. 39 (3): 53–60. PMC 2148750. PMID 1308373.
  2. DE2162744 idem H Adams, G Kronberg, B Takman, U.S. Patent 3,812,147 (1974 to Astra Pharma Prod).
  3. Org. Synth. 1950, 30, 62. DOI: 10.15227/orgsyn.030.0062
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