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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
Structure of PRILOCAINE

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)

HIDE SMILES / InChI

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 ( + / - )

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

2003
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
Health Status: unhealthy
Age Group: 6 years
Sex: M
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
Health Status: unhealthy
Age Group: 6 years
Sex: M
Sources:
PubMed

PubMed

TitleDatePubMed
Prilocaine versus lignocaine for minor lid procedures.
2000 Aug
[Comparative study between 5% prilocaine and 2% mepivacaine by the subarachnoid route in transurethral resections].
2000 May
[Experiences with liposuction of established surgeons].
2001
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
Local anaesthetic block copolymer system undergoing phase transition on dilution with water.
2001 Aug
Topical anesthetics update: EMLA and beyond.
2001 Dec
Oral sucrose compares favourably with lidocaine-prilocaine cream for pain relief during venepuncture in neonates.
2001 Feb
Comparison of EMLA cream versus placebo in children receiving distraction therapy for venepuncture.
2001 Feb
Lidocaine and prilocaine toxicity in a patient receiving treatment for mollusca contagiosa.
2001 Feb
Hyperpigmentation following the use of Emla cream.
2001 Jan
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
Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells.
2001 Jun 15
Split-skin grafting with lidocaine-prilocaine cream: A meta-analysis of efficacy and safety in geriatric versus nongeriatric patients.
2001 Mar
LET versus EMLA for pretreating lacerations: a randomized trial.
2001 Mar
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
Comparison of the effect of lidocaine-epinephrine and prilocaine-felypressine to alter macrophage functions.
2001 May
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
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
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
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
Methemoglobinemia.
2001 Sep
Treatment of gustatory sweating with botulinum toxin: special aspects.
2001 Sep-Oct
Noninvasive drug delivery.
2001 Winter
[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
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 Mon Mar 31 19:32:33 GMT 2025
Edited
by admin
on Mon Mar 31 19:32:33 GMT 2025
Record UNII
046O35D44R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPITOCAINE
JAN  
Preferred Name English
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
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
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 [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
PROPANAMIDE, N-(2-METHYLPHENYL)-2-(PROPYLAMINO)-
Systematic Name English
ASTRA-1512
Code English
Prilocaine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QN01BB04
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
EMA ASSESSMENT REPORTS FORTACIN (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
WHO-ATC N01BB54
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
NDF-RT N0000175682
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
WHO-VATC QN01BB54
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
WHO-ATC N01BB04
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
NDF-RT N0000175976
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
NDF-RT N0000007681
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
EMA ASSESSMENT REPORTS PRILOCAINE (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
NCI_THESAURUS C245
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
Code System Code Type Description
WIKIPEDIA
PRILOCAINE
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
DRUG BANK
DB00750
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
MERCK INDEX
m9132
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY Merck Index
INN
1641
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
LACTMED
Prilocaine
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID7031955
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
FDA UNII
046O35D44R
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
PUBCHEM
4906
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
RS_ITEM_NUM
1560990
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
NSC
40027
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
IUPHAR
7276
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
211-957-0
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
SMS_ID
100000092015
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
CAS
17676-07-2
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
SUPERSEDED
CHEBI
8404
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
HSDB
3386
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
NCI_THESAURUS
C47685
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
MESH
D011318
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
EVMPD
SUB10041MIG
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
ChEMBL
CHEMBL1194
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
DAILYMED
046O35D44R
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
DRUG CENTRAL
2265
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
USAN
JJ-23
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
RXCUI
8686
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY RxNorm
CAS
721-50-6
Created by admin on Mon Mar 31 19:32:33 GMT 2025 , Edited by admin on Mon Mar 31 19:32:33 GMT 2025
PRIMARY
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METABOLIC ENZYME -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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BASIS OF STRENGTH->SUBSTANCE
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