Prilocaine
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| AHFS/Drugs.com | Monograph |
| MedlinePlus | a603026 |
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| Protein binding | 55% |
| Metabolism | Hepatic and renal |
| Elimination half-life | 10-150 minutes, longer with impaired hepatic or renal function |
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100.010.871  |
| Chemical and physical data | |
| Formula | C13H20N2O |
| Molar mass | 220.311 g/mol |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
| Melting point | 37 to 38 °C (99 to 100 °F) |
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Prilocaine (/ˈpraɪləˌkeɪn/[1]) 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.[2]
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. It is used as an eutectic mixture with lidocaine, 50% w/w, as lidocaine/prilocaine. The mixture is an oil with a melting point of 18 °C (64 °F). A 5% emulsion preparation, containing 2.5% each of lidocaine/prilocaine, is marketed by APP Pharmaceuticals under the trade name EMLA (an abbreviation for eutectic mixture of local anesthetics).[3]
Compendial status
Notes
- ↑ "Prilocaine". Merriam-Webster Dictionary. Retrieved 2016-01-21.
- ↑ Patel, Vinod; Morrissey, John (2011-09-15). Practical and Professional Clinical Skills. Oxford University Press. p. 267. ISBN 9780199585618.
- ↑ "Topical Anesthesia Use in Children: Eutectic Mixture of Local Anesthetics". Medscape.com. Retrieved 2014-01-07.
- ↑ The United States Pharmacopeial Convention, Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test, archived from the original on 5 July 2010, retrieved 10 July 2009
See also