Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H20N2O |
Molecular Weight | 220.3112 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCNC(C)C(=Nc1ccccc1C)O
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 | 220.3112 |
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 Date1.07170562E12 |
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 |
---|---|---|
Prilocaine versus lignocaine for minor lid procedures. | 2000 Aug |
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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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Topical anesthetics in children: agents and techniques that equally comfort patients, parents, and clinicians. | 2001 Aug |
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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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Oral sucrose compares favourably with lidocaine-prilocaine cream for pain relief during venepuncture in neonates. | 2001 Feb |
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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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[Anesthesia with EMLA cream: a promising application for plastic surgery]. | 2001 Jun-Jul |
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Dermal pharmacokinetics of microemulsion formulations determined by in vivo microdialysis. | 2001 Mar |
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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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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 |
|
Blood flow changes in human dental pulps when capsaicin is applied to the adjacent gingival mucosa. | 2001 Nov |
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Pain experience during transvaginal aspiration of immature oocytes. | 2001 Nov |
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Quality of anaesthesia for insertion of tension-free vaginal tape using local analgesia and sedation. | 2001 Nov |
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Dermatosurgery using subcutaneous infusion anesthesia with prilocaine and ropivacaine in children. | 2001 Nov-Dec |
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Plasma concentrations of lignocaine and prilocaine after a 24-h application of analgesic cream (EMLA) to leg ulcers. | 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 |
|
EMLA or Ametop, and for how long? | 2001 Oct |
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Re: reduction in pain associated with open carpal tunnel decompression. | 2001 Oct |
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Antimicrobial activity of ropivacaine and other local anaesthetics. | 2001 Oct |
|
The effect of lidocaine/prilocaine cream on an experimental wound healing model. | 2001 Sep |
|
Topical anesthesia with or without propofol sedation versus retrobulbar/peribulbar anesthesia for cataract extraction: prospective randomized trial. | 2001 Sep |
|
The efficacy of a range of contact media as coupling agents in extracorporeal shockwave lithotripsy. | 2001 Sep |
|
Clinical and radiographic evaluation of pulpotomies performed under intrapulpal injection of anaesthetic solution. | 2001 Sep |
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Use of EMLA: is it an injection free alternative? | 2001 Spring |
|
[Management of leg ulcers in the elderly]. | 2002 Apr |
|
Vascular and neural mechanisms of ACh-mediated vasodilation in the forearm cutaneous microcirculation. | 2002 Feb |
|
Effects of dental local anaesthetics in cardiac transplant recipients. | 2002 Feb 9 |
|
Evidence that the human cutaneous venoarteriolar response is not mediated by adrenergic mechanisms. | 2002 Jan 15 |
|
Use of negatively charged cyclodextrins for the simultaneous enantioseparation of selected anesthetic drugs by capillary electrophoresis-mass spectrometry. | 2002 Jan 15 |
|
In vitro effects of some anesthetic drugs on enzymatic activity of human red blood cell glucose 6-phosphate dehydrogenase. | 2002 Jan-Feb |
|
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 |
|
Lidocaine iontophoresis versus eutectic mixture of local anesthetics (EMLA) for IV placement in children. | 2002 Jun |
|
Topical anesthesia for minor gynecological procedures: a review. | 2002 Mar |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 20:55:47 UTC 2021
by
admin
on
Fri Jun 25 20:55:47 UTC 2021
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Record UNII |
046O35D44R
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN01BB04
Created by
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EMA ASSESSMENT REPORTS |
FORTACIN (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
Created by
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WHO-ATC |
N01BB54
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NDF-RT |
N0000175682
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WHO-VATC |
QN01BB54
Created by
admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
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WHO-ATC |
N01BB04
Created by
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NDF-RT |
N0000175976
Created by
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NDF-RT |
N0000007681
Created by
admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
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EMA ASSESSMENT REPORTS |
PRILOCAINE (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
Created by
admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
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NCI_THESAURUS |
C245
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Code System | Code | Type | Description | ||
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PRILOCAINE
Created by
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PRIMARY | |||
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DB00750
Created by
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PRIMARY | |||
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M9132
Created by
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PRIMARY | Merck Index | ||
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1641
Created by
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PRIMARY | |||
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Prilocaine
Created by
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PRIMARY | |||
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721-50-6
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PRIMARY | |||
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046O35D44R
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PRIMARY | |||
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4906
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7276
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PRIMARY | |||
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211-957-0
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17676-07-2
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3386
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PRIMARY | |||
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C47685
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D011318
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SUB10041MIG
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CHEMBL1194
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2265
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1560990
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8686
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PRIMARY | RxNorm | ||
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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 |
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 |