Prilocaine

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Prilocaine
Prilocaine.svg
Names
Pronunciation/ˈprləˌkn/[1]
Trade namesCitanest, Prilotekal, others
  • (RS)-N-(2-methylphenyl)-N2-propylalaninamide
Clinical data
Drug classLocal anesthetic (amide)[2]
Main usesNumbing a specific area, nerve block, spinal anesthesia[3][2]
Side effectsDizziness, high blood pressure, low blood pressure, nausea, arrhythmia[2]
Pregnancy
category
  • AU: A
  • US: B (No risk in non-human studies)
Routes of
use
Subcutaneous
External links
AHFS/Drugs.comMonograph
US NLMPrilocaine
MedlinePlusa603026
Legal
License data
Legal status
Pharmacokinetics
Protein binding55%
MetabolismLiver and kidney
Elimination half-life10-150 minutes, longer with impaired liver or kidney function
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) checkY
  • Key:MVFGUOIZUNYYSO-UHFFFAOYSA-N checkY

Prilocaine, sold under the trade name Citanest among others, is a local anesthetic used for numbing a specific area, for a nerve block, or as part of spinal anesthesia.[3][2] It is used by injection.[4] It is also available as a lidocaine/prilocaine cream.[2]

Side effects may include dizziness, high blood pressure, low blood pressure, nausea, and arrhythmia.[2] Other side effects may include methemoglobinemia and cardiac arrest.[2] Use in pregnancy appears to be relatively safe.[5] It is an amide type local anesthetic.[2]

Prilocaine was approved for medical use in the United States in 1965.[4] In the United Kingdom 50 mL of a 1% solution costs about £5.[2] Manufacture has been discontinued in the United States as of 2012;[6] though it previously costs about 1 USD for 1.8 mL of a 4% solution.[7]

Medical uses

Dosage

Typically 1 to 2 mL is used, though in someone who is at least 75 kg up to 15 mL of 4% solution may be used.[4] Dosing should be based on ideal body weight.[2]

Combinations

It is given as a combination with the vasoconstrictor epinephrine. 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, under the trade name EMLA (an abbreviation for eutectic mixture of local anesthetics).[8]

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.[9]

History

It was first prepared by Claes Tegner and Nils Löfgren.

Society and culture

Compendial status

References

  1. "Prilocaine". Merriam-Webster Dictionary. Retrieved 2016-01-21.
  2. 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 2.9 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 1409. ISBN 978-0857114105.
  3. 3.0 3.1 "DailyMed - CITANEST PLAIN- prilocaine hydrochloride injection, solution". dailymed.nlm.nih.gov. Archived from the original on 30 October 2021. Retrieved 29 October 2021.
  4. 4.0 4.1 4.2 "Prilocaine Monograph for Professionals". Drugs.com. Archived from the original on 5 October 2021. Retrieved 29 October 2021.
  5. Giglio, JA; Lanni, SM; Laskin, DM; Giglio, NW (February 2009). "Oral health care for the pregnant patient". Journal (Canadian Dental Association). 75 (1): 43–8. PMID 19239743.
  6. "Determination That CITANEST (Prilocaine Hydrochloride) Injection, 1%, 2%, and 3%, and CITANEST PLAIN (Prilocaine Hydrochloride) Injection, 4%, Were Not Withdrawn From Sale for Reasons of Safety or Effectiveness". Archived from the original on 9 November 2020. Retrieved 29 October 2021.
  7. "Citanest HCl Plain Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 14 May 2021. Retrieved 29 October 2021.
  8. "Topical Anesthesia Use in Children: Eutectic Mixture of Local Anesthetics". Medscape.com. Archived from the original on 2013-10-22. Retrieved 2014-01-07.
  9. Patel V, Morrissey J (2011-09-15). Practical and Professional Clinical Skills. Oxford University Press. p. 267. ISBN 9780199585618. Archived from the original on 2021-04-28. Retrieved 2021-01-20.
  10. 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

External links

External sites:
Identifiers: