Prilocaine

Prilocaine
Names
Pronunciation/ˈpraɪləˌkeɪn/[1]
Trade namesCitanest, Prilotekal, others
IUPAC name
  • (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]
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Pregnancy
category
  • AU: A
  • US: B (No risk in non-human studies)
    Routes of
    use    		Subcutaneous
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa603026
    Legal
    License data
    Legal status
    • AU: S4 (Prescription only)
    • US: ℞-only
    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)
    SMILES
    • O=C(Nc1ccccc1C)C(NCCC)C
    InChI
    • 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. 1 2 3 4 5 6 7 8 9 10 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 1409. ISBN 978-0857114105.
    3. 1 2 "DailyMed - CITANEST PLAIN- prilocaine hydrochloride injection, solution". dailymed.nlm.nih.gov. Archived from the original on 30 October 2021. Retrieved 29 October 2021.
    4. 1 2 3 "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
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