Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H20N2O.ClH |
Molecular Weight | 256.772 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCNC(C)C(=O)NC1=C(C)C=CC=C1
InChI
InChIKey=BJPJNTKRKALCPP-UHFFFAOYSA-N
InChI=1S/C13H20N2O.ClH/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);1H
DescriptionSources: http://www.drugbank.ca/drugs/DB00750
Sources: http://www.drugbank.ca/drugs/DB00750
Prilocaine is a local anesthetic that is similar pharmacologically to lidocaine. Prilocaine binds to the intracellular surface of sodium channels which blocks the subsequent influx of sodium into the cell. Action potential propagation and never function is, therefore, prevented. This block is reversible and when the drug diffuses away from the cell, sodium channel function is restored and nerve propagation returns. Prilocaine acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers. Currently, Prilocaine is used most often for infiltration anesthesia in dentistry.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833 |
|||
Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00750 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | ORAQIX Approved UseOraqix is an amide local anesthetic indicated for adults who require localized anesthesia in periodontal pockets during scaling and/or root planing. Launch Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
106 ng/mL |
42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.07 μg/mL |
1.5 g single, topical dose: 1.5 g route of administration: Topical experiment type: SINGLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26000 ng × min/mL |
42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.8 h |
42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
70 min |
single, intravenous |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45% |
1.5 g single, topical dose: 1.5 g route of administration: Topical experiment type: SINGLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
6 mg/kg single, transdermal Dose: 6 mg/kg Route: transdermal Route: single Dose: 6 mg/kg Sources: |
unhealthy, 6 years n = 1 Health Status: unhealthy Age Group: 6 years Sex: M Population Size: 1 Sources: |
Other AEs: Methemoglobinemia... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Methemoglobinemia | 6 mg/kg single, transdermal Dose: 6 mg/kg Route: transdermal Route: single Dose: 6 mg/kg Sources: |
unhealthy, 6 years n = 1 Health Status: unhealthy Age Group: 6 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
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Pharmacological management of pain and anxiety during emergency procedures in children. | 2001 |
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A randomised, double-blind, placebo-controlled, comparative study of topical skin analgesics and the anxiety and discomfort associated with venous cannulation. | 2001 Apr 28 |
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Local anaesthetic block copolymer system undergoing phase transition on dilution with water. | 2001 Aug |
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[Neurotoxicity of intrathecal lidocaine]. | 2001 Aug-Sep |
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Topical anesthetics update: EMLA and beyond. | 2001 Dec |
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The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing. | 2001 Dec |
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Hyperpigmentation following the use of Emla cream. | 2001 Jan |
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Comparison of topical EMLA 5% oral adhesive to benzocaine 20% on the pain experienced during palatal anesthetic infiltration in children. | 2001 Jan-Feb |
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Intrapocket anesthesia for scaling and root planing: results of a double-blind multicenter trial using lidocaine prilocaine dental gel. | 2001 Jul |
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A comparison of 1% prilocaine with 0.5% ropivacaine for outpatient-based surgery under axillary brachial plexus block. | 2001 Jul |
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Effects of prilocaine and articaine on human leucocytes and reactive oxygen species in vitro. | 2001 Jul |
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[Some aspects of epidural anesthesia in patients with chronic renal insufficiency]. | 2001 Jul-Aug |
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Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells. | 2001 Jun 15 |
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Dermal pharmacokinetics of microemulsion formulations determined by in vivo microdialysis. | 2001 Mar |
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[Citanest recalled--bad and inconsistent decision by Astra pharmaceutical company]. | 2001 Mar 7 |
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[Peripheral nerve block. An overview of new developments in an old technique]. | 2001 May |
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[Varicose vein operations with tumescence local anesthesia--an effective method]. | 2001 May |
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Emla versus ice as a topical anesthetic. | 2001 May |
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Plasma levels of lidocaine and prilocaine after application of Oraqix, a new intrapocket anesthetic, in patients with advanced periodontitis. | 2001 May |
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Safety and pharmacokinetics of EMLA in the treatment of postburn pruritus in pediatric patients: a pilot study. | 2001 May-Jun |
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Evaluation of pain management interventions for neonatal circumcision pain. | 2001 May-Jun |
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A randomized double-blind, placebo-controlled trial of the EMLA patch for the reduction of pain associated with intramuscular injection in four to six-year-old children. | 2001 Nov |
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Reflection spectroscopy of analgesized skin. | 2001 Nov |
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Pain on injection of prilocaine plain vs. lidocaine with epinephrine. A prospective double-blind study. | 2001 Oct |
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[New uses of EMLA: anesthesia for relief of pain caused by hemorrhoid thrombosis]. | 2001 Oct |
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EMLA--1 h is not enough for venous cannulation. | 2001 Oct |
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EMLA or Ametop, and for how long? | 2001 Oct |
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Effect of an intervention to reduce procedural pain and distress for children with HIV infection. | 2001 Oct-Nov |
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[Ovarian puncture in fertilization in vitro: what analgesia?]. | 2001 Sep |
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Topical anesthesia with or without propofol sedation versus retrobulbar/peribulbar anesthesia for cataract extraction: prospective randomized trial. | 2001 Sep |
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The efficacy of a range of contact media as coupling agents in extracorporeal shockwave lithotripsy. | 2001 Sep |
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Clinical and radiographic evaluation of pulpotomies performed under intrapulpal injection of anaesthetic solution. | 2001 Sep |
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Methemoglobinemia. | 2001 Sep |
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Use of EMLA: is it an injection free alternative? | 2001 Spring |
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Noninvasive drug delivery. | 2001 Winter |
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The use of EMLA for an intraoral soft-tissue biopsy in a needle phobic: a case report. | 2001 Winter |
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[Management of leg ulcers in the elderly]. | 2002 Apr |
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A comparison of prilocaine and lidocaine for intravenous regional anaesthesia for forearm fracture reduction in children. | 2002 Feb |
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[Tumescent technique for local anesthesia]. | 2002 Feb |
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Effects of dental local anaesthetics in cardiac transplant recipients. | 2002 Feb 9 |
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Evidence that the human cutaneous venoarteriolar response is not mediated by adrenergic mechanisms. | 2002 Jan 15 |
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In vitro effects of some anesthetic drugs on enzymatic activity of human red blood cell glucose 6-phosphate dehydrogenase. | 2002 Jan-Feb |
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Reader questions pain and peritumoral injection. | 2002 Jan-Feb |
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Use of EMLA cream with vasectomy. | 2002 Jul |
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The use of glyceryl trinitrate ointment with EMLA cream for i.v. cannulation in children undergoing routine surgery. | 2002 Jun |
|
A clinical study to evaluate the efficacy of ELA-Max (4% liposomal lidocaine) as compared with eutectic mixture of local anesthetics cream for pain reduction of venipuncture in children. | 2002 Jun |
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Lidocaine iontophoresis versus eutectic mixture of local anesthetics (EMLA) for IV placement in children. | 2002 Jun |
|
EMLA cream-induced irritant contact dermatitis. | 2002 Mar |
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Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1. | 2002 May |
|
Amethocaine-lidocaine cream, a new topical formulation for preventing venopuncture-induced pain in children. | 2002 May-Jun |
Sample Use Guides
Use the included blunt tipped applicator to apply gel to gingival margins and periodontal pockets
Route of Administration:
Dental
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833
Prilocaine inhibited FMLP-induced CL in human leucocytes (94+/-1%, at 1 mM). In cell-free experiments, prilocaine (22+/-6%, at 1 mM) caused concentration-dependent inhibition in xanthine-xanthine oxidase-induced CL.
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NCI_THESAURUS |
C245
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DTXSID2031956
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MJW015BAPH
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CHEMBL1194
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DBSALT000962
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92163
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217-244-0
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m9132
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C48012
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88208-29-1
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SUPERSEDED |
ACTIVE MOIETY
SUBSTANCE RECORD