Prilocaine

Prilocaine

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a603026
Pregnancy category	B (U.S.)
ATC code	N01BB04 (WHO)
Pharmacokinetic data
Protein binding	55%
Metabolism	Hepatic and renal
Elimination half-life	10-150 minutes, longer with impaired hepatic or renal function
Identifiers
IUPAC name (RS)-N-(2-methylphenyl)-N2-propylalaninamide
CAS Number	721-50-6 Y
PubChem CID	4906
DrugBank	DB00750 Y
ChemSpider	4737 Y
UNII	046O35D44R
KEGG	D00553 Y
ChEBI	CHEBI:8404 Y
ChEMBL	ChEMBL1194 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C13H20N2O
Molar mass	220.311 g/mol
3D model (JSmol)	Interactive image
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) Y Key:MVFGUOIZUNYYSO-UHFFFAOYSA-N Y
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List of terms related to Prilocaine

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Prilocaine /ˈpraɪlkeɪn/ 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.

Prilocaine synthesis

Compendial status

• United States Pharmacopeia 31

See also

• Lidocaine/prilocaine