Prilocaine

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Prilocaine
Prilocaine.png
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa603026
Pregnancy
category
ATC code
Pharmacokinetic data
Protein binding55%
MetabolismHepatic and renal
Elimination half-life10-150 minutes, longer with impaired hepatic or renal function
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC13H20N2O
Molar mass220.311 g/mol
3D model (JSmol)
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Prilocaine /ˈprl[invalid input: 'ɵ']kn/ 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 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).

In some patients, ortho-toluidine, a metabolite of prilocaine may cause methemoglobinemia, which may be treated with methylene blue.

Maximum dosage for dental use: 8.0 mg/kg (2.7 mg/lb), with a maximum dose of 500 mg.

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

Synthesis

Prilocaine can be synthesized from o-toluidine, 2-bromopropionyl bromide, and n-butylamine.[1]

Prilocaine synthesis

Compendial status

Notes

  1. Template:Cite doi
  2. The United States Pharmacopeial Convention. "Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test". Retrieved 10 July 2009.

See also


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