Prilocaine

Prilocaine (/ˈpraɪləˌkeɪn/) is a local anesthetic of the amino amide type first prepared by Claes Tegner and Nils Löfgren. In its injectable form (trade name Citanest), it is often used in dentistry. It is also often combined with lidocaine as a topical preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia. As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA).

Prilocaine
Clinical data
Trade namesCitanest
AHFS/Drugs.comMonograph
MedlinePlusa603026
License data
Pregnancy
category
  • AU: A
Routes of
administration		Subcutaneous
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding55%
MetabolismLiver and kidney
Elimination half-life10-150 minutes, longer with impaired liver or kidney function
Identifiers
  • (RS)-N-(2-methylphenyl)-N2-propylalaninamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.871
Chemical and physical data
FormulaC13H20N2O
Molar mass220.316 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point37 to 38 °C (99 to 100 °F)
  • O=C(Nc1ccccc1C)C(NCCC)C
  • InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16) Y
  • Key:MVFGUOIZUNYYSO-UHFFFAOYSA-N Y
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