Clinical data
AHFS/ Monograph
MedlinePlus a603026
  • B (U.S.)
ATC code N01BB04 (WHO)
Pharmacokinetic data
Protein binding 55%
Metabolism Hepatic and renal
Biological half-life 10-150 minutes, longer with impaired hepatic or renal function
CAS Number 721-50-6 YesY
PubChem (CID) 4906
DrugBank DB00750 YesY
ChemSpider 4737 YesY
UNII 046O35D44R YesY
KEGG D00553 YesY
ECHA InfoCard 100.010.871
Chemical and physical data
Formula C13H20N2O
Molar mass 220.311 g/mol
3D model (Jmol) Interactive image
Chirality Racemic mixture
Melting point 37 to 38 °C (99 to 100 °F)

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).


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]

People with pseudocholinesterase deficiency may have difficulty metabolizing this anesthetic.


It is given as a combination with the vasoconstrictor epinephrine under the trade name Citanest Forte.

Compendial status


  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. The United States Pharmacopeial Convention. "Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test". Retrieved 10 July 2009.

See also

This article is issued from Wikipedia - version of the 12/2/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.