Prilocaine

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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 ;
PubChem CID	4906;
DrugBank	DB00750 ;
ChemSpider	4737 ;
UNII	046O35D44R;
KEGG	D00553 ;
ChEBI	CHEBI:8404 ;
ChEMBL	ChEMBL1194 ;
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
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) ; Key:MVFGUOIZUNYYSO-UHFFFAOYSA-N ;
(verify)

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

Overview

Prilocaine /ˈpraɪl[invalid input: 'ɵ']keɪn/ 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.

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

v t e Anesthetics: Local anesthetics (N01B)
Esters of aminobenzoic acid	Amylocaine, Benzocaine, Butacaine, Chloroprocaine, Dimethocaine, Meprylcaine, Orthocaine, Propoxycaine, Procaine, Proparacaine, Risocaine, Tetracaine
Amides	Articaine, Bupivacaine, Carticaine, Cinchocaine, Etidocaine, Levobupivacaine, Lidocaine, Mepivacaine, Prilocaine, Ropivacaine, Trimecaine
Esters of benzoic acid	Cocaine, Piperocaine
Other	Hexylcaine, Iontocaine, Lidocaine/prilocaine