Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H20N2O |
Molecular Weight | 220.3107 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCNC(C)C(=O)NC1=CC=CC=C1C
InChI
InChIKey=MVFGUOIZUNYYSO-UHFFFAOYSA-N
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)
Molecular Formula | C13H20N2O |
Molecular Weight | 220.3107 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
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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 |
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 |
PubMed
Title | Date | PubMed |
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Prilocaine versus lignocaine for minor lid procedures. | 2000 Aug |
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[Comparative study between 5% prilocaine and 2% mepivacaine by the subarachnoid route in transurethral resections]. | 2000 May |
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[Experiences with liposuction of established surgeons]. | 2001 |
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Pharmacological management of pain and anxiety during emergency procedures in children. | 2001 |
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Pain management for neonatal circumcision. | 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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From cocaine to ropivacaine: the history of local anesthetic drugs. | 2001 Aug |
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Local anaesthetic block copolymer system undergoing phase transition on dilution with water. | 2001 Aug |
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Topical anesthetics update: EMLA and beyond. | 2001 Dec |
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Oral sucrose compares favourably with lidocaine-prilocaine cream for pain relief during venepuncture in neonates. | 2001 Feb |
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Comparison of EMLA cream versus placebo in children receiving distraction therapy for venepuncture. | 2001 Feb |
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Lidocaine and prilocaine toxicity in a patient receiving treatment for mollusca contagiosa. | 2001 Feb |
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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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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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Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells. | 2001 Jun 15 |
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Split-skin grafting with lidocaine-prilocaine cream: A meta-analysis of efficacy and safety in geriatric versus nongeriatric patients. | 2001 Mar |
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LET versus EMLA for pretreating lacerations: a randomized trial. | 2001 Mar |
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Making vaccines more acceptable--methods to prevent and minimize pain and other common adverse events associated with vaccines. | 2001 Mar 21 |
|
[Citanest recalled--bad and inconsistent decision by Astra pharmaceutical company]. | 2001 Mar 7 |
|
EMLA anaesthetic cream for sharp leg ulcer debridement: a review of the clinical evidence for analgesic efficacy and tolerability. | 2001 Mar-Apr |
|
[Varicose vein operations with tumescence local anesthesia--an effective method]. | 2001 May |
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Comparison of the effect of lidocaine-epinephrine and prilocaine-felypressine to alter macrophage functions. | 2001 May |
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Emla versus ice as a topical anesthetic. | 2001 May |
|
Towards evidence based emergency medicine: best BETs from the Manchester Royal Infirmary. EMLA or amethocaine (tetracaine) for topical analgesia in children. | 2001 May |
|
The anesthetic onset and duration of a new lidocaine/prilocaine gel intra-pocket anesthetic (Oraqix) for periodontal scaling/root planing. | 2001 May |
|
Plasma levels of lidocaine and prilocaine after application of Oraqix, a new intrapocket anesthetic, in patients with advanced periodontitis. | 2001 May |
|
The influence of two different dental local anaesthetic solutions on the haemodynamic responses of children undergoing restorative dentistry: a randomised, single-blind, split-mouth study. | 2001 May 12 |
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Diffusive transport properties of some local anesthetics applicable for iontophoretic formulation of the drugs. | 2001 May 7 |
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Safety and pharmacokinetics of EMLA in the treatment of postburn pruritus in pediatric patients: a pilot study. | 2001 May-Jun |
|
Evaluation of pain management interventions for neonatal circumcision pain. | 2001 May-Jun |
|
Efficacy of subcutaneous and topical local anaesthesia for pain relief after resection of malignant breast tumours. | 2001 Nov |
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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 |
|
Re: reduction in pain associated with open carpal tunnel decompression. | 2001 Oct |
|
Antimicrobial activity of ropivacaine and other local anaesthetics. | 2001 Oct |
|
Clinical and radiographic evaluation of pulpotomies performed under intrapulpal injection of anaesthetic solution. | 2001 Sep |
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Methemoglobinemia. | 2001 Sep |
|
Treatment of gustatory sweating with botulinum toxin: special aspects. | 2001 Sep-Oct |
|
Noninvasive drug delivery. | 2001 Winter |
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[Tumescent technique for local anesthesia]. | 2002 Feb |
|
Vascular and neural mechanisms of ACh-mediated vasodilation in the forearm cutaneous microcirculation. | 2002 Feb |
|
Local anesthesia with EMLA cream for maxillary sinus puncture. | 2002 Jan |
|
Characteristics of drug substances in oily solutions. Drug release rate, partitioning and solubility. | 2002 Jan 31 |
|
Reader questions pain and peritumoral injection. | 2002 Jan-Feb |
|
The use of glyceryl trinitrate ointment with EMLA cream for i.v. cannulation in children undergoing routine surgery. | 2002 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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:32:33 GMT 2025
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Record UNII |
046O35D44R
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Record Status |
Validated (UNII)
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WHO-VATC |
QN01BB04
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EMA ASSESSMENT REPORTS |
FORTACIN (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
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WHO-ATC |
N01BB54
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NDF-RT |
N0000175682
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WHO-VATC |
QN01BB54
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WHO-ATC |
N01BB04
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N0000175976
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NDF-RT |
N0000007681
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EMA ASSESSMENT REPORTS |
PRILOCAINE (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
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NCI_THESAURUS |
C245
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Code System | Code | Type | Description | ||
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PRILOCAINE
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PRIMARY | |||
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DB00750
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PRIMARY | |||
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m9132
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PRIMARY | Merck Index | ||
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1641
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Prilocaine
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DTXSID7031955
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046O35D44R
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4906
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1560990
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40027
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7276
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211-957-0
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100000092015
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17676-07-2
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8404
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3386
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C47685
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D011318
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SUB10041MIG
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CHEMBL1194
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046O35D44R
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2265
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JJ-23
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8686
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721-50-6
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
UNSPECIFIED
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |