Prilocaine

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Local anesthetic of the amino amide type

title: "Prilocaine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["local-anesthetics", "anilides", "drugs-developed-by-astrazeneca", "propionamides", "amino-acid-derivatives"] description: "Local anesthetic of the amino amide type" topic_path: "general/local-anesthetics" source: "https://en.wikipedia.org/wiki/Prilocaine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Local anesthetic of the amino amide type ::

| verifiedrevid = 464214246 | image = Prilocaine.svg | image_class = skin-invert-image | width = 200px | chirality = Racemic mixture

| tradename = Citanest | Drugs.com = | MedlinePlus = a603026 | licence_EU = yes | DailyMedID = Prilocaine | licence_US = | pregnancy_AU = A | pregnancy_AU_comment = | pregnancy_US = B | pregnancy_US_comment = | pregnancy_category= | dependency_liability = | addiction_liability = | routes_of_administration = Subcutaneous | class = | ATCvet = | ATC_prefix = N01 | ATC_suffix = BB04 | ATC_supplemental =

| legal_AU = S4 | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =

| bioavailability = | protein_bound = 55% | metabolism = Liver and kidney | elimination_half-life = 10-150 minutes, longer with impaired liver or kidney function

| index2_label = as HCl | CAS_number_Ref = | CAS_number = 721-50-6 | PubChem = 4906 | IUPHAR_ligand = 7276 | DrugBank_Ref = | DrugBank = DB00750 | ChemSpiderID_Ref = | ChemSpiderID = 4737 | UNII_Ref = | UNII = 046O35D44R | KEGG_Ref = | KEGG = D00553 | KEGG2_Ref = | KEGG2 = D01243 | ChEBI_Ref = | ChEBI = 8404 | ChEMBL_Ref = | ChEMBL = 1194

| IUPAC_name = (RS)-N-(2-methylphenyl)-N2-propylalaninamide | C=13 | H=20 | N=2 | O=1 | smiles = O=C(Nc1ccccc1C)C(NCCC)C | StdInChI_Ref = | StdInChI = 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) | StdInChIKey_Ref = | StdInChIKey = MVFGUOIZUNYYSO-UHFFFAOYSA-N | melting_point = 37 | melting_high = 38

Prilocaine () 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.

Combinations

It is given as a combination with the vasoconstrictor epinephrine under the trade name Citanest Forte. It is used as a eutectic mixture with lidocaine, 50% w/w, as lidocaine/prilocaine. The mixture is an oil with a melting point of 18 C. 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).

Compendial status

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/1/14/Prilocaine_synthesis.svg" caption="105439887}} (2016 to 重庆康乐制药有限公司)."] ::

The amidation between o-toluidine [95-53-4] (1) and 2-bromopropionyl bromide [563-76-8] (2) leads to 2-bromo-N-(2-methylphenyl)propanamide [19397-79-6] (3). Displacement of the remaining halide with propylamine [107-10-8] (4) completed the synthesis of prilocaine (5).

References

References

  1. (2011-09-15). "Practical and Professional Clinical Skills". Oxford University Press.
  2. "Topical Anesthesia Use in Children: Eutectic Mixture of Local Anesthetics". Medscape.com.
  3. The United States Pharmacopeial Convention. "Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test".
  4. Löfgren, Nils; Tegnér, Claës; Arwidsson, Barbro; Varde, E.; Westin, Gertrud (1960). "Studies on Local Anesthetics. XX. Synthesis of Some alpha-Monoalkylamino-2-methylpropionanilides. A New Useful Local Anesthetic.". Acta Chemica Scandinavica 14: 486–490. doi:10.3891/acta.chem.scand.14-0486.
  5. Anon., {{Cite patent. GB. 839943 (to Astra Apotekarnes Kem Fab).
  6. Lofgren Nils Magnus, Tegner Claes Philip, {{US patent. 3160662 (1964 to Astra Apotekarnes Kem Fab).
  7. Demare, Patricia; Regla, Ignacio (2012). "Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course". Journal of Chemical Education. 89 (1): 147–149. doi:10.1021/ed100838a.
  8. 沈文晖, 杨忠鑫, 葛小强, 张宇生, 邹玉龙, 张强, 杨继斌, 蔡中文, {{Cite patent. CN. 105439887 (2016 to 重庆康乐制药有限公司).

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

local-anestheticsanilidesdrugs-developed-by-astrazenecapropionamidesamino-acid-derivatives