Prilocaine

Prilocaine
Clinical data
Trade namesCitanest
AHFS/Drugs.comMonograph
MedlinePlusa603026
License data
Pregnancy
category
  • AU: A
Routes of
administration
Subcutaneous
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding55%
MetabolismLiver and kidney
Elimination half-life10-150 minutes, longer with impaired liver or kidney function
Identifiers
  • (RS)-N-(2-methylphenyl)-N2-propylalaninamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.871 Edit this at Wikidata
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
  (verify)

Prilocaine (/ˈpraɪləˌkeɪn/) 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 (64 °F). 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

Synthesis: Patents: Revised: Sino:

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).

See also


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