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Identification
NamePrilocaine
Accession NumberDB00750  (APRD00180)
TypeSmall Molecule
GroupsApproved
Description

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)

Structure
Thumb
Synonyms
2-(Propylamino)-O-propionotoluidide
2-Methyl-alpha-propylaminopropionanilide
alpha-N-Propylamino-2-methylpropionanilide
N-(2-Methylphenyl)-2-(propylamino)propanamide
O-Methyl-2-propylaminopropionanilide
O-Methyl-alpha-propylaminopropionanilide
Prilocain
Prilocaina
Prilocaïne
Prilocaine base
Prilocainum
Propitocaine
External Identifiers
  • Astra 1512
  • L 67
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
4% Citanest Plain Dentalsolution40 mgblock/infiltrationDentsply Canada Limited2015-12-23Not applicableCanada
AgoneazekittopicalAlvix Laboratories, LLC2016-01-12Not applicableUs
Dentsply 4% Prilocaine Hydrochloride Dental Injectionsolution40 mgblock/infiltrationDentsply Canada Limited1964-12-312016-06-03Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Citanest Plaininjection, solution40 mg/mLdentalDentsply Pharmaceutical Inc.1965-11-18Not applicableUs
Prilocaine Hydrochlorideinjection, solution40 mg/mLsubcutaneousSeptodont Inc.2011-01-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CitanestAstraZeneca
PrilotekalGoldshield
TakiprilMeduna
XylonestAstraZeneca
Brand mixtures
NameLabellerIngredients
4% Citanest Forte Dental With Epinephrine 1:200,000Dentsply Canada Limited
Citanest ForteDentsply Pharmaceutical Inc.
Dentsply 4% Prilocaine and Epinephrine Injection 1:200,000Dentsply Canada Limited
EmlaActavis Pharma, Inc.
Emla CrmAstrazeneca Canada Inc
Emla PatchAstrazeneca Canada Inc
IV Infusion CpiPure Tek Corporation
Lidocaine 2.5% and Prilocaine 2.5% CreamWelgo, Llc
Lidocaine and PrilocaineImpax Generics
Lidocaine-prilocaine-cream BaseHumco Holding Group, Inc.
OraqixDentsply Pharmaceutical
Prilocaine HCl 4% Epineph 1:200000injNovocol Pharmaceutical Of Canada Inc
Prilocaine Hydrochloride With EpinephrineSeptodont Inc.
Relador Pak PlusAccelis Pharma
Relador Pak With Occlusive DressingAccelis Pharma
Salts
Name/CASStructureProperties
Prilocaine Hydrochloride
ThumbNot applicableDBSALT000962
Categories
UNII046O35D44R
CAS number721-50-6
WeightAverage: 220.3107
Monoisotopic: 220.157563272
Chemical FormulaC13H20N2O
InChI KeyInChIKey=MVFGUOIZUNYYSO-UHFFFAOYSA-N
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)
IUPAC Name
N-(2-methylphenyl)-2-(propylamino)propanamide
SMILES
CCCNC(C)C(=O)NC1=CC=CC=C1C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • N-arylamide
  • Aminotoluene
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as a local anaesthetic and is often used in dentistry.
PharmacodynamicsPrilocaine 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.
Mechanism of actionPrilocaine 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding98%
MetabolismNot Available
Route of eliminationPrilocaine is metabolized in both the liver and the kidney and excreted via the kidney.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Prilocaine Action PathwayDrug actionSMP00401
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9557
Blood Brain Barrier+0.9285
Caco-2 permeable+0.7888
P-glycoprotein substrateSubstrate0.6968
P-glycoprotein inhibitor INon-inhibitor0.8019
P-glycoprotein inhibitor IINon-inhibitor0.9165
Renal organic cation transporterNon-inhibitor0.895
CYP450 2C9 substrateNon-substrate0.7803
CYP450 2D6 substrateNon-substrate0.5124
CYP450 3A4 substrateNon-substrate0.5253
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6298
Ames testNon AMES toxic0.7941
CarcinogenicityNon-carcinogens0.6653
BiodegradationNot ready biodegradable0.9577
Rat acute toxicity2.1374 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9676
hERG inhibition (predictor II)Non-inhibitor0.8577
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutionblock/infiltration40 mg
Kittopical
Injection, solutiondental
Injection, solutiondental40 mg/mL
Solutionblock/infiltration
Patchtopical
Kit
Creamtopical
Gelperiodontal
Geltopical
Liquidblock/infiltration
Injection, solutionsubcutaneous40 mg/mL
Injection, solutionsubcutaneous
Kittopical
Prices
Unit descriptionCostUnit
Prilocaine hcl powder3.98USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6031007 No1997-04-012017-04-01Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point37-38 °CPhysProp
boiling point159-162 °C at 1.00E-01 mm HgPhysProp
water solubility541 mg/LNot Available
logP2.11HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.326 mg/mLALOGPS
logP1.87ALOGPS
logP2.68ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.51ChemAxon
pKa (Strongest Basic)8.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.13 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.86 m3·mol-1ChemAxon
Polarizability25.98 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.45 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis Reference

DrugSyn.org

US3160662
General ReferencesNot Available
External Links
ATC CodesN01BB04N01BB54
AHFS Codes
  • 72:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.4 KB)
Interactions
Drug Interactions
Drug
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Prilocaine.
Amyl NitriteThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Prilocaine.
BenzocaineThe risk or severity of adverse effects can be increased when Benzocaine is combined with Prilocaine.
ButalbitalThe risk or severity of adverse effects can be increased when Butalbital is combined with Prilocaine.
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Prilocaine.
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Prilocaine.
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Prilocaine.
FlutamideThe risk or severity of adverse effects can be increased when Flutamide is combined with Prilocaine.
HyaluronidaseThe risk or severity of adverse effects can be increased when Hyaluronidase is combined with Prilocaine.
IsosorbideThe risk or severity of adverse effects can be increased when Isosorbide is combined with Prilocaine.
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Isosorbide Dinitrate is combined with Prilocaine.
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Isosorbide Mononitrate is combined with Prilocaine.
LidocaineThe risk or severity of adverse effects can be increased when Lidocaine is combined with Prilocaine.
MafenideThe risk or severity of adverse effects can be increased when Mafenide is combined with Prilocaine.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Prilocaine.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Prilocaine.
NitrofurantoinThe risk or severity of adverse effects can be increased when Nitrofurantoin is combined with Prilocaine.
NitroglycerinThe risk or severity of adverse effects can be increased when Nitroglycerin is combined with Prilocaine.
NitroprussideThe risk or severity of adverse effects can be increased when Nitroprusside is combined with Prilocaine.
PhenazopyridineThe risk or severity of adverse effects can be increased when Phenazopyridine is combined with Prilocaine.
PhenobarbitalThe risk or severity of adverse effects can be increased when Phenobarbital is combined with Prilocaine.
PhenytoinThe risk or severity of adverse effects can be increased when Phenytoin is combined with Prilocaine.
PrimaquineThe risk or severity of adverse effects can be increased when Primaquine is combined with Prilocaine.
QuinineThe risk or severity of adverse effects can be increased when Quinine is combined with Prilocaine.
Sodium NitriteThe risk or severity of adverse effects can be increased when Prilocaine is combined with Sodium Nitrite.
SulfadiazineThe risk or severity of adverse effects can be increased when Sulfadiazine is combined with Prilocaine.
Technetium Tc-99m tilmanoceptPrilocaine may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
ZopicloneThe risk or severity of adverse effects can be increased when Zopiclone is combined with Prilocaine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is respon...
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on July 29, 2016 01:52