Prilocaine
 | |
| Clinical data | |
|---|---|
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a603026 |
| Pregnancy category |
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| ATC code | N01BB04 (WHO) |
| 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  |
| PubChem (CID) | 4906 |
| IUPHAR/BPS | 7276 |
| DrugBank |
DB00750 |
| ChemSpider |
4737 |
| UNII |
046O35D44R |
| KEGG |
D00553 |
| ChEBI |
CHEBI:8404 |
| ChEMBL |
CHEMBL1194 |
| ECHA InfoCard | 100.010.871 |
| Chemical and physical data | |
| Formula | C13H20N2O |
| Molar mass | 220.311 g/mol |
| 3D model (Jmol) | Interactive image |
| 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.
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.
- ↑ The United States Pharmacopeial Convention. "Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test". Retrieved 10 July 2009.