U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PRILOCAINE

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)

HIDE SMILES / InChI

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 ( + / - )

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.

CNS Activity

Curator's Comment:: Prilocaine crosses the blood-brain and placental barriers

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ORAQIX

Approved Use

Oraqix is an amide local anesthetic indicated for adults who require localized anesthesia in periodontal pockets during scaling and/or root planing.

Launch Date

1.07170562E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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...
Other AEs:
Methemoglobinemia
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Prilocaine versus lignocaine for minor lid procedures.
2000 Aug
Pharmacological management of pain and anxiety during emergency procedures in children.
2001
Pain management for neonatal circumcision.
2001
A randomised, double-blind, placebo-controlled, comparative study of topical skin analgesics and the anxiety and discomfort associated with venous cannulation.
2001 Apr 28
From cocaine to ropivacaine: the history of local anesthetic drugs.
2001 Aug
Topical anesthetics in children: agents and techniques that equally comfort patients, parents, and clinicians.
2001 Aug
Local anaesthetic block copolymer system undergoing phase transition on dilution with water.
2001 Aug
[Neurotoxicity of intrathecal lidocaine].
2001 Aug-Sep
Oral sucrose compares favourably with lidocaine-prilocaine cream for pain relief during venepuncture in neonates.
2001 Feb
Comparison of topical EMLA 5% oral adhesive to benzocaine 20% on the pain experienced during palatal anesthetic infiltration in children.
2001 Jan-Feb
A comparison of 1% prilocaine with 0.5% ropivacaine for outpatient-based surgery under axillary brachial plexus block.
2001 Jul
Effects of prilocaine and articaine on human leucocytes and reactive oxygen species in vitro.
2001 Jul
[Anesthesia with EMLA cream: a promising application for plastic surgery].
2001 Jun-Jul
Dermal pharmacokinetics of microemulsion formulations determined by in vivo microdialysis.
2001 Mar
[Peripheral nerve block. An overview of new developments in an old technique].
2001 May
[Varicose vein operations with tumescence local anesthesia--an effective method].
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
Diffusive transport properties of some local anesthetics applicable for iontophoretic formulation of the drugs.
2001 May 7
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
Pain experience during transvaginal aspiration of immature oocytes.
2001 Nov
Quality of anaesthesia for insertion of tension-free vaginal tape using local analgesia and sedation.
2001 Nov
Dermatosurgery using subcutaneous infusion anesthesia with prilocaine and ropivacaine in children.
2001 Nov-Dec
Plasma concentrations of lignocaine and prilocaine after a 24-h application of analgesic cream (EMLA) to leg ulcers.
2001 Oct
[New uses of EMLA: anesthesia for relief of pain caused by hemorrhoid thrombosis].
2001 Oct
EMLA--1 h is not enough for venous cannulation.
2001 Oct
EMLA or Ametop, and for how long?
2001 Oct
Re: reduction in pain associated with open carpal tunnel decompression.
2001 Oct
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
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
Patents

Sample Use Guides

Use the included blunt tipped applicator to apply gel to gingival margins and periodontal pockets
Route of Administration: Dental
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 Fri Jun 25 20:55:47 UTC 2021
Edited
by admin
on Fri Jun 25 20:55:47 UTC 2021
Record UNII
046O35D44R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRILOCAINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
PRILOCAINE [INN]
Common Name English
PROPITOCAINE
JAN  
Common Name English
NSC-40027
Code English
ORAQIX COMPONENT PRILOCAINE
Common Name English
PRILOCAINE [VANDF]
Common Name English
EMLA COMPONENT PRILOCAINE
Common Name English
O-PROPIONOTOLUIDIDE, 2-(PROPYLAMINO)-
Common Name English
2-METHYL-.ALPHA.-PROPYLAMINOPROPIONANILIDE
Systematic Name English
PRILOCAINE COMPONENT OF ORAQIX
Common Name English
DL-(+/-)-PRILOCAINE
Common Name English
ASTRA-1515
Code English
PRILOCAINE [HSDB]
Common Name English
PRILOCAINE [USP MONOGRAPH]
Common Name English
FORTACIN COMPONENT PRILOCAINE
Brand Name English
O-METHYL-2-PROPYLAMINOPROPIONANILIDE
Common Name English
PROPITOCAINE [JAN]
Common Name English
PRILOCAINE [WHO-DD]
Common Name English
PRILOCAINE [MART.]
Common Name English
PRILOCAINE [MI]
Common Name English
PRILOCAINE [ORANGE BOOK]
Common Name English
(+/-)-PRILOCAINE
Common Name English
N-(2-METHYLPHENYL)-2-(PROPYLAMINO)PROPANAMIDE
Systematic Name English
PRILOCAINE [USAN]
Common Name English
N-(2,6-DIMETHYLPHENYL)-2-(PROPYLAMINO)PROPANAMIDE
Systematic Name English
PRILOCAINE [USP-RS]
Common Name English
(+/-)-N-(2-PROPYLAMINOPROPIONYL)-2-TOLUIDINE
Systematic Name English
PRILOCAINE [EP MONOGRAPH]
Common Name English
PRILOCAINE COMPONENT OF FORTACIN
Brand Name English
PROPANAMIDE, N-(2-METHYLPHENYL)-2-(PROPYLAMINO)-
Systematic Name English
PRILOCAINE COMPONENT OF EMLA
Common Name English
ASTRA-1512
Code English
Classification Tree Code System Code
WHO-VATC QN01BB04
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
EMA ASSESSMENT REPORTS FORTACIN (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
WHO-ATC N01BB54
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
NDF-RT N0000175682
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
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
WHO-ATC N01BB04
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
NDF-RT N0000175976
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
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
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
NCI_THESAURUS C245
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
Code System Code Type Description
WIKIPEDIA
PRILOCAINE
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
DRUG BANK
DB00750
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
MERCK INDEX
M9132
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY Merck Index
INN
1641
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
LACTMED
Prilocaine
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
EPA CompTox
721-50-6
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
FDA UNII
046O35D44R
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
PUBCHEM
4906
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
IUPHAR
7276
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-957-0
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
CAS
17676-07-2
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
SUPERSEDED
HSDB
3386
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
NCI_THESAURUS
C47685
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
MESH
D011318
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
EVMPD
SUB10041MIG
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL1194
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
DRUG CENTRAL
2265
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
USP_CATALOG
1560990
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY USP-RS
RXCUI
8686
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY RxNorm
CAS
721-50-6
Created by admin on Fri Jun 25 20:55:47 UTC 2021 , Edited by admin on Fri Jun 25 20:55:47 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY