PRILOCAINE
- Molecular FormulaC13H20N2O
- Average mass220.311 Da
- ASTRA 1512
- ASTRA 1515
- ASTRA-1512
- ASTRA-1515
- L 67
Product Ingredients
| INGREDIENT | UNII | CAS | INCHI KEY |
|---|---|---|---|
| Prilocaine hydrochloride | MJW015BAPH | 1786-81-8 | BJPJNTKRKALCPP-UHFFFAOYSA-N |
Prilocaine is a local anesthetic used in dental procedures.
A local anesthetic that is similar pharmacologically to lidocaine. Currently, it is used most often for infiltration anesthesia in dentistry. (From AMA Drug Evaluations Annual, 1992, p165)
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]
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]
NMR
![1 H-nuclear magnetic resonance ( 1 H-NMR) spectra of prilocaine solution after sterilization with the assignment of the prilocaine hydrogens. [Prilocaine] = 5 mM, 20°C, 500 MHz.](https://www.researchgate.net/profile/Francisco-Groppo/publication/23458262/figure/fig3/AS:394557704425486@1471081295276/1-H-nuclear-magnetic-resonance-1-H-NMR-spectra-of-prilocaine-solution-after.png)
1 H-nuclear magnetic resonance ( 1 H-NMR) spectra of prilocaine solution after sterilization with the assignment of the prilocaine hydrogens. [Prilocaine] = 5 mM, 20°C, 500 MHz.
Compendial status
Table 1 The common types of local anesthetics
| COMPOUND | STRUCTURE | TIME TO MARKET | APPLICATION METHODS |
|---|---|---|---|
| Procaine | 1904 | Infiltration anesthesia, conduction anesthesia, subarachnoid anesthesia and epidural anesthesia | |
| Chloroprocaine | 1952 | Infiltration anesthesia, epidural anesthesia and conduction anesthesia | |
| Hydroxyprocaine | 1960 | Infiltration anesthesia | |
| Tetracaine | 1988 | Conduction anesthesia, subarachnoid anesthesia and epidural anesthesia | |
| Oxybuprocaine | 1975 | Topical anesthesia | |
| Tutocaine | 1976 | Topical anesthesia and infiltration anesthesia | |
| Butacaine | 1976 | Topical anesthesia and infiltration anesthesia | |
| Dimethocaine | 1938 | Topical anesthesia and infiltration anesthesia | |
| Thiocaine | Halt sales | Topical anesthesia and infiltration anesthesia | |
| Lidocaine | 1948 | Conduction anesthesia and epidural anesthesia | |
| Mepivacaine | 1986 | Infiltration anesthesia, conduction anesthesia, epidural anesthesia and topical anesthesia | |
| Bupivacaine | 2000 | Infiltration anesthesia, conduction anesthesia and epidural anesthesia | |
| Ropivacaine | 1996 | Infiltration anesthesia, conduction anesthesia and epidural anesthesia | |
| Trimecaine | 1965 | Infiltration anesthesia, surface anesthesia and epidural anesthesia | |
| Prilocaine | 1993 | Infiltration anesthesia, topical anesthesia and epidural anesthesia | |
| Etidocaine | 1976 | Epidural anesthesia | |
| Pyrrocaine | 1964 | Conduction anesthesia and epidural anesthesia | |
| Butanilicaine | 1982 | Infiltration anesthesia and conduction anesthesia | |
| Cinchocaine | 1985 | Topical anesthesia, subarachnoid anesthesia and epidural anesthesia | |
| Articaine | 2002 | Infiltration anesthesia and subarachnoid anesthesia | |
| Dyclonine | 1956 | Topical anesthesia | |
| Falicaine | 1957 | Topical anesthesia | |
| Quinisocaine | 1957 | Topical anesthesia | |
| Pramocaine | 1977 | Topical anesthesia | |
| Diperodon | 1980 | Topical anesthesia | |
| Heptacaine | 1984 | Infiltration anesthesia |
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Synthesis Reference
SYN
English: N. Lofgren and C. Tegner, Acta Chem. Scand., 14, 486 (1960). DOI number: 10.3891/acta.chem.scand.14-0486
SYN
SUN
Prilocaine, 2-(propylamino)-o-propiontoluidine (2.2.14), is structurally related to the exact same group as ethidocaine, yet it differs structurally in that during synthesis, o-toluidine is used instead of 2,6-dimethylaniline, and instead of a butyric acid, a fragment of propionic acid, and a terminal propylethylamine group is replaced with a propylamine group. In order to synthesize prilocaine, o-toluidine is reacted with bromopropionyl bromide, and the resulting bromopropionyltoluidide (2.2.13) is then reacted with propylamine, which gives prilocaine [22,23].
SYN
SYN
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|
| Clinical data | |
|---|---|
| Trade names | Citanest |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a603026 |
| License data |
|
| Pregnancy category |
|
| Routes of administration |
Subcutaneous |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Protein binding | 55% |
| Metabolism | Liver and kidney |
| Elimination half-life | 10-150 minutes, longer with impaired liver or kidney function |
| Identifiers | |
| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.010.871  |
| Chemical and physical data | |
| Formula | C13H20N2O |
| Molar mass | 220.316 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
| Melting point | 37 to 38 °C (99 to 100 °F) |
| (verify) | |
References
- ^ “Prilocaine”. Merriam-Webster Dictionary. Retrieved 2016-01-21.
- ^ Patel V, Morrissey J (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
External links
- “Prilocaine”. Drug Information Portal. U.S. National Library of Medicine.
- “Prilocaine hydrochloride”. Drug Information Portal. U.S. National Library of Medicine.
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