Prilocaine

Brand names: Citanest® Plain Dental

Chemical formula:

Last updated: 7/1/2002

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A local anesthetic, used as the hydrochloride salt.

1 : 1 mixture (racemate)

Systematic (IUPAC) name
(RS)-N-(2-methylphenyl)-N2-propylalaninamide
Identifiers
CAS number	721-50-6
ATC code	N01BB04
PubChem	4906
DrugBank	APRD00180
Chemical data
Formula	C13H20N2O
Mol. mass	220.311 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	55%
Metabolism	Hepatic and renal
Half life	10-150 minutes, longer with impaired hepatic or renal function
Excretion	?
Therapeutic considerations
Pregnancy cat.	B (U.S.)
Legal status
Routes	?
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Prilocaine (pronounced /ˈpraɪlɵkeɪn/) is a local anesthetic of the amino amide type. 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 commoly used for intravenous regional anaesthesia (IVRA).

In some patients, a metabolite of prilocaine may cause the unusual side-effect of methaemoglobinaemia. And 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.

Contents 1 Toxicology 2 Compendial status 3 Notes 4 See also

Toxicology

This section requires expansion.

Compendial status

• United States Pharmacopeia 31 ^[1]

Notes

1. ^ The United States Pharmacopeial Convention. "Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test". http://www.usp.org/USPNF/notices/lidocaineAndPrilocaine.html. Retrieved 10 July 2009. 

See also

• Lidocaine/prilocaine

v • d • e Anesthetics: Local anesthetics - primarily sodium channel blockers (N01B) Esters Esters of aminobenzoic acid Amylocaine • Benzocaine • Butacaine • Chloroprocaine • Dimethocaine • Meprylcaine • Metabutoxycaine • Orthocaine • Propoxycaine • Procaine • Proxymetacaine • Risocaine • Tetracaine Esters of benzoic acid 3-(p-Fluorobenzoyloxy)tropane • Cocaine • Cyclomethycaine • Piperocaine Other esters Hexylcaine Amides Articaine • Bupivacaine # /Levobupivacaine/Ropivacaine • Carticaine • Cinchocaine • Etidocaine • Lidocaine #  • Mepivacaine • Prilocaine • Trimecaine Combinations Iontocaine • Lidocaine/prilocaine #WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III

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