Prilocaine

For research use only. Not for therapeutic Use.

  • CAT Number: A000423
  • CAS Number: 721-50-6
  • Molecular Formula: C13H20N2O
  • Molecular Weight: 220.31
  • Purity: ≥95%
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Prilocaine (CAT: A000423) is a local anesthetic belonging to the amino amide class. It is commonly used for its numbing properties in various medical and dental procedures. Prilocaine works by blocking sodium channels on the neuronal cell membrane, which inhibits the generation and transmission of nerve impulses. This action effectively reduces pain perception in the targeted area, making it useful for local anesthesia.


Catalog Number A000423
CAS Number 721-50-6
Synonyms

NSC 40027

Molecular Formula C13H20N2O
Purity ≥95%
Target Na+/K+ ATPase
Storage 3 years -20C powder
Overview of Clinical Research

Prilocaine is a sodium channel antagonist, used as a local anaesthetic.

IUPAC Name N-(2-methylphenyl)-2-(propylamino)propanamide
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)
InChIKey MVFGUOIZUNYYSO-UHFFFAOYSA-N
SMILES CCCNC(C)C(=O)NC1=CC=CC=C1C
Reference

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1. Anaesth Crit Care Pain Med. 2016 Dec;35(6):417-421. doi: 10.1016/j.accpm.2016.03.005. Epub 2016 Jun 21.Prilocaine spinal anesthesia for ambulatory surgery: A review of the available studies.Boublik J(1), Gupta R(2), Bhar S(3), Atchabahian A(4).</div>
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Transient neurologic symptoms (TNS) led to the abandonment of intrathecal lidocaine. We reviewed the published literature for information about the duration of action and side effects of intrathecal prilocaine, which has been recently reintroduced in Europe. Medline and EMBASE databases were searched for the time period from 1966 to 2015. Fourteen prospective and one retrospective study were retrieved. The duration of the surgical block can be adjusted using doses between 40 and 80mg. Hyperbaric prilocaine in doses as low as 10mg can be used for perianal procedures. Four cases of TNS in 486 patients were reported in prospective studies, and none in 5000 cases in a retrospective data set. Spinal prilocaine appears to be safe and reliable for day case anesthesia. However, as chloroprocaine has a shorter duration and a lower risk of TNS and urinary retention, the indications for prilocaine remain to be defined.</div>
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2. J Liposome Res. 2011 Mar;21(1):81-7. doi: 10.3109/08982101003754393. Epub 2010 Apr 30.Anesthetic efficacy of liposomal prilocaine in maxillary infiltration anesthesia.Wiziack Zago PM(1), Baroni DB, Groppo FC, de Paula E, Ranali J, Volpato MC.</div>
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Animal studies have shown that liposome encapsulation increases prilocaine anesthetic efficacy. This randomized, blind, crossover, three-period study evaluated the anesthetic efficacy of liposome-encapsulated 3% prilocaine, compared to 3% plain prilocaine and 3% prilocaine with 0.03IU/mL felypressin, after a 1.8-mL infiltration in the buccal sulcus of the maxillary right canine, in 32 volunteers. Anesthesia success, onset, and duration of pulpal and gingival anesthesia in the lateral incisor, and canine and first premolar were evaluated. Injection pain was assessed by a visual analog scale (VAS). Results were submitted to Kruskal-Wallis (onset and duration of pulpal anesthesia), Tukey (VAS), Friedman (duration of gingival anesthesia), and log-rank and McNemar tests (anesthesia success) (&alpha;&thinsp;=&thinsp;5%). Liposomal prilocaine did not differ from plain prilocaine (P&thinsp;&gt;&thinsp;0.05), but presented lower anesthesia success and duration for canine, premolar, and gingivalanesthesia (P&thinsp;&lt;&thinsp;0.05) than prilocaine with felypressin. Liposomal prilocaine did not differ from the other formulations concerning onset and anesthesia success for the lateral incisor (p&thinsp;&gt;&thinsp;0.05); plain prilocaine presented lower success rates and slower onset of anesthesia for this tooth, in comparison to prilocaine with felypressin (P&thinsp;&lt;&thinsp;0.05). No differences were observed among the formulations in relation to duration of anesthesia for lateral incisor, VAS scores, and onset of gingival and pulpal anesthesia for the canine and premolar (P&thinsp;&gt;&thinsp;0.05). In conclusion, liposomal prilocaine presents similar anesthetic efficacy in relation to plain prilocaine and lower efficacy, in comparison to prilocaine with felypressin in maxillary infiltration. Prilocaine does not seem to benefit from liposomal encapsulation.</div>
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3. Drugs. 1993 Jul;46(1):126-51. doi: 10.2165/00003495-199346010-00008.Eutectic lidocaine/prilocaine cream. A review of the topical anaesthetic/analgesic efficacy of a eutectic mixture of local anaesthetics(EMLA).Buckley MM(1), Benfield P.</div>
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Eutectic lidocaine/prilocaine cream 5% is a eutectic mixture of the local anaesthetics lidocaine (lignocaine) 25 mg/g and prilocaine 25 mg/g that provides dermal anaesthesiaanalgesia following topical application. The principal indication in which eutectic lidocaine/prilocaine cream has been studied is the management of pain associated with venipuncture or intravenous cannulation, where significantly greater pain relief than placebo, with equivalent efficacy to ethyl chloride spray and lidocaine infiltration, has been demonstrated. In dermatological surgery, eutectic lidocaine/prilocaine cream offers effective pain relief in children undergoing curettage of molluscum contagiosum lesions, and in adults undergoing split-skin graft harvesting. Particular benefit has also been shown with use of eutectic lidocaine/prilocaine cream in association with treatment of condylomata acuminata in both men and women, and it appears to provide a useful alternative to lidocaine infiltration in this context. Further research in such indications as paediatric lumbar puncture, minor otological surgery, and minor gynaecological, urological and andrological procedures is likely to further broaden the profile of clinical use for eutectic lidocaine/prilocaine cream. Eutectic lidocaine/prilocaine cream has a very favourable tolerability profile, transient and mild skin blanching and erythema being the most frequent adverse events to occur in association with its application to skin. The potential for inducing methaemoglobinaemia, attributed to a metabolite of the prilocaine component of the formulation, prohibits its use in infants younger than 6 months. In summary, eutectic lidocaine/prilocaine cream is a novel formulation of local anaesthetics that has proven to be effective and well-tolerated in the relief of pain associated with various minor interventions in adults and children.</div>
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