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Prilocaine

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Prilocaine

Prilocaine
Systematic (IUPAC) name
(RS)-N-(2-methylphenyl)-N2-propylalaninamide
Clinical data
AHFS/Drugs.com
MedlinePlus
Pregnancy cat.
Legal status
?
Pharmacokinetic data
Protein binding 55%
Metabolism Hepatic and renal
Half-life 10-150 minutes, longer with impaired hepatic or renal function
Identifiers
CAS number  YesY
ATC code N01
PubChem
DrugBank
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
Chemical data
Formula C13H20N2O 
Mol. mass 220.311 g/mol
 YesY   

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 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. ^ Löfgren, Nils (1960). "Studies on Local Anesthetics. XX. Synthesis of Some alpha-Monoalkylamino-2-methylpropionanilides. A New Useful Local Anesthetic.". Acta Chemica Scandinavica 14: 486–490.  
  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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