Prilocaine

Prilocaine

Systematic (IUPAC) name
(RS)-N-(2-methylphenyl)-N2-propylalaninamide
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a603026
Pregnancy cat.	B (U.S.)
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	721-50-6 Y
ATC code	N01BB04
PubChem	CID 4906
DrugBank	DB00750
ChemSpider	4737 Y
UNII	046O35D44R Y
KEGG	D00553 Y
ChEBI	CHEBI:8404 Y
ChEMBL	CHEMBL1194 Y
Chemical data
Formula	C13H20N2O
Mol. mass	220.311 g/mol
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
Y (what is this?)  (verify)

Prilocaine /ˈpraɪlɵkeɪn/ 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, a metabolite of prilocaine may cause the unusual side effect of 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.

Compendial status

• United States Pharmacopeia 31 ^[1]

Notes

See also

• Lidocaine/prilocaine