Etidocaine

Chemical compound

AU: B1

Routes of
administrationParenteralATC code

N01BB07 (WHO)

Legal statusLegal status

US: ℞-only

Pharmacokinetic dataBioavailabilityn/aMetabolismHepaticElimination half-life2.5 hoursExcretionRenalIdentifiers

IUPAC name

N-(2,6-dimethylphenyl)-
2-(ethyl(propyl)amino)butanamide

CAS Number

36637-18-0^N

PubChem CID

37497

IUPHAR/BPS

2621

DrugBank

DB08987^N

ChemSpider

34400^Y

UNII

I6CQM0F31V

KEGG

D04095^Y

ChEBI

CHEBI:4904^Y

ChEMBL

ChEMBL492^Y

CompTox Dashboard (EPA)

DTXSID1023027

ECHA InfoCard100.048.296

Chemical and physical dataFormulaC₁₇H₂₈N₂OMolar mass276.424 g·mol⁻¹3D model (JSmol)

Interactive image

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)

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]

Synthesis

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

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

External links

Duranest (RxList)

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid

Aminobenzoic	Benzocaine Benzonatate Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine
Benzoic	Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine
ArCO2- (not para-amino or Ph)	Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane