Prilocaine

Prilocaine
Systematic (IUPAC) name
(RS)-N-(2-methylphenyl)-N2-propylalaninamide
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a603026
Pregnancy
category
  • B (U.S.)
Pharmacokinetic data
Protein binding 55%
Metabolism Hepatic and renal
Biological half-life 10-150 minutes, longer with impaired hepatic or renal function
Identifiers
CAS Number 721-50-6 YesY
ATC code N01BB04 (WHO)
PubChem CID 4906
IUPHAR/BPS 7276
DrugBank DB00750 YesY
ChemSpider 4737 YesY
UNII 046O35D44R YesY
KEGG D00553 YesY
ChEBI CHEBI:8404 YesY
ChEMBL CHEMBL1194 YesY
Chemical data
Formula C13H20N2O
Molar mass 220.311 g/mol
Chirality Racemic mixture
  (verify)

Prilocaine (/ˈpraɪləˌkeɪn/[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).

Contraindications

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.

Combinations

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

Compendial status

Notes

  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 Saturday, April 02, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.