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Prilocaine (/ˈprləˌkn/[1]) 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
Prilocaine.svg
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa603026
License data
Pregnancy
category
  • B (U.S.)
ATC code
Pharmacokinetic data
Protein binding55%
MetabolismHepatic and renal
Elimination half-life10-150 minutes, longer with impaired hepatic or renal function
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.871 Edit this at Wikidata
Chemical and physical data
FormulaC13H20N2O
Molar mass220.311 g/mol g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point37 to 38 °C (99 to 100 °F)
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Contents

ContraindicationsEdit

In some patients, ortho-toluidine, a metabolite of prilocaine, may cause methemoglobinemia, which may be treated with methylene blue. Prilocaine may also be contraindicated in people with sickle cell anemia, anemia, or symptomatic hypoxia.[2]

CombinationsEdit

It is given as a combination with the vasoconstrictor epinephrine under the trade name Citanest Forte. It is used as an eutectic mixture with lidocaine, 50% w/w, as lidocaine/prilocaine. The mixture is an oil with a melting point of 18 °C (64 °F). A 5% emulsion preparation, containing 2.5% each of lidocaine/prilocaine, is marketed by APP Pharmaceuticals under the trade name EMLA (an abbreviation for eutectic mixture of local anesthetics).[3]

Compendial statusEdit

NotesEdit

  1. ^ "Prilocaine". Merriam-Webster Dictionary. Retrieved 2016-01-21.
  2. ^ Patel, Vinod; Morrissey, John (2011-09-15). Practical and Professional Clinical Skills. Oxford University Press. p. 267. ISBN 9780199585618.
  3. ^ "Topical Anesthesia Use in Children: Eutectic Mixture of Local Anesthetics". Medscape.com. Retrieved 2014-01-07.
  4. ^ The United States Pharmacopeial Convention, Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test, archived from the original on 5 July 2010, retrieved 10 July 2009

See alsoEdit