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

Details

Stereochemistry RACEMIC
Molecular Formula C13H20N2O
Molecular Weight 220.3107
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRILOCAINE

SMILES

CCCNC(C)C(=O)NC1=C(C)C=CC=C1

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

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
[Experiences with liposuction of established surgeons].
2001
[Comment on the article "Use of EMLA cream and ropivacaine indacryocystorhinostomy with locoregional anesthesia and sedation"].
2001 Apr
A randomised, double-blind, placebo-controlled, comparative study of topical skin analgesics and the anxiety and discomfort associated with venous cannulation.
2001 Apr 28
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
The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing.
2001 Dec
Intrapocket anesthesia for scaling and root planing: results of a double-blind multicenter trial using lidocaine prilocaine dental gel.
2001 Jul
Eutectic mixture of local anesthetics reduces pain during intravenous catheter insertion in the pediatric patient.
2001 Jun
[Anesthesia with EMLA cream: a promising application for plastic surgery].
2001 Jun-Jul
Factors affecting patients' and potential patients' choices among anaesthetics for periodontal recall visits.
2001 Mar
Split-skin grafting with lidocaine-prilocaine cream: A meta-analysis of efficacy and safety in geriatric versus nongeriatric patients.
2001 Mar
[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
Comparison of the effect of lidocaine-epinephrine and prilocaine-felypressine to alter macrophage functions.
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
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
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
Reflection spectroscopy of analgesized skin.
2001 Nov
Quality of anaesthesia for insertion of tension-free vaginal tape using local analgesia and sedation.
2001 Nov
Subcutaneous infusion anesthesia for dermatologic surgery in children: are we ready?
2001 Nov-Dec
Local anesthesia prior to the insertion of peripherally inserted central catheters.
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
Effect of an intervention to reduce procedural pain and distress for children with HIV infection.
2001 Oct-Nov
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
EMLA versus nitrous oxide for venous cannulation in children.
2001 Sep
Treatment of gustatory sweating with botulinum toxin: special aspects.
2001 Sep-Oct
The use of EMLA for an intraoral soft-tissue biopsy in a needle phobic: a case report.
2001 Winter
Intravenous regional guanethidine blockade in the treatment of post-traumatic complex regional pain syndrome type 1 (algodystrophy) of the hand.
2002 Apr
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction.
2002 Apr
Lidocaine-prilocaine cream versus tetracaine gel for procedural pain in children.
2002 Apr
A comparison of prilocaine and lidocaine for intravenous regional anaesthesia for forearm fracture reduction in children.
2002 Feb
Vascular and neural mechanisms of ACh-mediated vasodilation in the forearm cutaneous microcirculation.
2002 Feb
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
Topical anesthesia for minor gynecological procedures: a review.
2002 Mar
The effects of age on neural blockade and hemodynamic changes after epidural anesthesia with ropivacaine.
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 Thu Jul 06 02:15:38 UTC 2023
Edited
by admin
on Thu Jul 06 02:15:38 UTC 2023
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 [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
Prilocaine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QN01BB04
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
EMA ASSESSMENT REPORTS FORTACIN (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
WHO-ATC N01BB54
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
NDF-RT N0000175682
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
WHO-VATC QN01BB54
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
WHO-ATC N01BB04
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
NDF-RT N0000175976
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
NDF-RT N0000007681
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
EMA ASSESSMENT REPORTS PRILOCAINE (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
NCI_THESAURUS C245
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
Code System Code Type Description
WIKIPEDIA
PRILOCAINE
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
DRUG BANK
DB00750
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
MERCK INDEX
M9132
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY Merck Index
INN
1641
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
LACTMED
Prilocaine
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID7031955
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
FDA UNII
046O35D44R
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
PUBCHEM
4906
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
RS_ITEM_NUM
1560990
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
NSC
40027
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
IUPHAR
7276
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
211-957-0
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
SMS_ID
100000092015
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
CAS
17676-07-2
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
SUPERSEDED
CHEBI
8404
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
HSDB
3386
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
NCI_THESAURUS
C47685
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
MESH
D011318
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
EVMPD
SUB10041MIG
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL1194
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
DAILYMED
046O35D44R
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
DRUG CENTRAL
2265
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
USAN
JJ-23
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
RXCUI
8686
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY RxNorm
CAS
721-50-6
Created by admin on Thu Jul 06 02:15:38 UTC 2023 , Edited by admin on Thu Jul 06 02:15:38 UTC 2023
PRIMARY
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