Prilocaine

Prilocaine

Systematic (IUPAC) name
(RS)-N-(2-methylphenyl)-N2-propylalaninamide
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a603026
Pregnancy category	B (U.S.)
Pharmacokinetic data
Protein binding	55%
Metabolism	Hepatic and renal
Biological half-life	10-150 minutes, longer with impaired hepatic or renal function
Identifiers
CAS Number	721-50-6 Y
ATC code	N01BB04 (WHO)
PubChem	CID: 4906
IUPHAR/BPS	7276
DrugBank	DB00750 Y
ChemSpider	4737 Y
UNII	046O35D44R Y
KEGG	D00553 Y
ChEBI	CHEBI:8404 Y
ChEMBL	CHEMBL1194 Y
Chemical data
Formula	C13H20N2O
Molecular 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
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Prilocaine /ˈpraɪloʊkeɪn/ 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 topical 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).

Contraindications

In some patients, ortho-toluidine, a metabolite of prilocaine, may cause methemoglobinemia, which may be treated with methylene blue. Prilocaine may also be contraindicated in people with sickle cell anemia, anemia, or symptomatic hypoxia.

People with pseudocholinesterase deficiency may have difficulty metabolizing this anesthetic.

Combinations

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

Compendial status

• United States Pharmacopeia 31

See also

• Lidocaine/prilocaine