Etidocaine

Etidocaine
Clinical data
Trade names	Duranest
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a603026
Pregnancy; category	AU: B1; ;
Routes of; administration	Parenteral
ATC code	N01BB07 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Hepatic
Elimination half-life	2.5 hours
Excretion	Renal
Identifiers
	IUPAC name N-(2,6-dimethylphenyl)-; 2-(ethyl(propyl)amino)butanamide;
CAS Number	36637-18-0 ;
PubChem CID	37497;
IUPHAR/BPS	2621;
DrugBank	DB08987 ;
ChemSpider	34400 ;
UNII	I6CQM0F31V;
KEGG	D04095 ;
ChEBI	CHEBI:4904 ;
ChEMBL	ChEMBL492 ;
CompTox Dashboard (EPA)	DTXSID1023027 ;
ECHA InfoCard	100.048.296
Chemical and physical data
Formula	C17H28N2O
Molar mass	276.424 g·mol−1
3D 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) ; Key:VTUSIVBDOCDNHS-UHFFFAOYSA-N ;
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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

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

^ 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)

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[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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