PRILOCAINE

First approved in 1965

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 Search

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	( + / - )

Description
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
reactive oxygen species biosynthetic process 41 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833	Inhibitor 8504
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00750	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021451s008lbl.pdf	Preventing		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
106 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021451s008lbl.pdf	42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE	LIDOCAINE	PRILOCAINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
0.07 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019941s021lbl.pdf	1.5 g single, topical dose: 1.5 g route of administration: Topical experiment type: SINGLE co-administered: LIDOCAINE	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021451s008lbl.pdf	42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE	LIDOCAINE	PRILOCAINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021451s008lbl.pdf	42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE	LIDOCAINE	PRILOCAINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
70 min DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019941s021lbl.pdf	single, intravenous		PRILOCAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
45% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019941s021lbl.pdf	1.5 g single, topical dose: 1.5 g route of administration: Topical experiment type: SINGLE co-administered: LIDOCAINE	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: https://pubmed.ncbi.nlm.nih.gov/22272683	unhealthy, 6 years Health Status: unhealthy Age Group: 6 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/22272683	Other AEs: Methemoglobinemia... Other AEs: Methemoglobinemia Sources: https://pubmed.ncbi.nlm.nih.gov/22272683

AEs

AE	Significance	Dose	Population
Methemoglobinemia		6 mg/kg single, transdermal Dose: 6 mg/kg Route: transdermal Route: single Dose: 6 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/22272683	unhealthy, 6 years Health Status: unhealthy Age Group: 6 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/22272683

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8404	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8404
ChemicalBook	CB8270843	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8270843
eMolecules	902352	https://www.emolecules.com/cgi-bin/more?vid=902352
MolPort	MolPort-005-935-583	https://www.molport.com/shop/molecule-link/MolPort-005-935-583
Selleck Chemicals	Prilocaine	http://www.selleckchem.com/products/Prilocaine.html

PubMed

Title	Date	PubMed
Prilocaine versus lignocaine for minor lid procedures.	2000 Aug	11040906
[Comparative study between 5% prilocaine and 2% mepivacaine by the subarachnoid route in transurethral resections].	2000 May	10902449
[Experiences with liposuction of established surgeons].	2001	11824336
Pharmacological management of pain and anxiety during emergency procedures in children.	2001	11393327
Pain management for neonatal circumcision.	2001	11269637
A randomised, double-blind, placebo-controlled, comparative study of topical skin analgesics and the anxiety and discomfort associated with venous cannulation.	2001 Apr 28	11352393
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001 Aug	11895133
Local anaesthetic block copolymer system undergoing phase transition on dilution with water.	2001 Aug	11457650
Topical anesthetics update: EMLA and beyond.	2001 Dec	11849263
Oral sucrose compares favourably with lidocaine-prilocaine cream for pain relief during venepuncture in neonates.	2001 Feb	11236045
Comparison of EMLA cream versus placebo in children receiving distraction therapy for venepuncture.	2001 Feb	11236044
Lidocaine and prilocaine toxicity in a patient receiving treatment for mollusca contagiosa.	2001 Feb	11174427
Hyperpigmentation following the use of Emla cream.	2001 Jan	11121330
Comparison of topical EMLA 5% oral adhesive to benzocaine 20% on the pain experienced during palatal anesthetic infiltration in children.	2001 Jan-Feb	11242723
A comparison of 1% prilocaine with 0.5% ropivacaine for outpatient-based surgery under axillary brachial plexus block.	2001 Jul	11429363
Effects of prilocaine and articaine on human leucocytes and reactive oxygen species in vitro.	2001 Jul	11421833
Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells.	2001 Jun 15	11403930
Split-skin grafting with lidocaine-prilocaine cream: A meta-analysis of efficacy and safety in geriatric versus nongeriatric patients.	2001 Mar	11304601
LET versus EMLA for pretreating lacerations: a randomized trial.	2001 Mar	11229943
Making vaccines more acceptable--methods to prevent and minimize pain and other common adverse events associated with vaccines.	2001 Mar 21	11257372
[Citanest recalled--bad and inconsistent decision by Astra pharmaceutical company].	2001 Mar 7	11301988
EMLA anaesthetic cream for sharp leg ulcer debridement: a review of the clinical evidence for analgesic efficacy and tolerability.	2001 Mar-Apr	11275800
[Varicose vein operations with tumescence local anesthesia--an effective method].	2001 May	11383083
Comparison of the effect of lidocaine-epinephrine and prilocaine-felypressine to alter macrophage functions.	2001 May	11379046
Emla versus ice as a topical anesthetic.	2001 May	11359502
Towards evidence based emergency medicine: best BETs from the Manchester Royal Infirmary. EMLA or amethocaine (tetracaine) for topical analgesia in children.	2001 May	11354215
The anesthetic onset and duration of a new lidocaine/prilocaine gel intra-pocket anesthetic (Oraqix) for periodontal scaling/root planing.	2001 May	11350509
Plasma levels of lidocaine and prilocaine after application of Oraqix, a new intrapocket anesthetic, in patients with advanced periodontitis.	2001 May	11350505
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	11384023
Diffusive transport properties of some local anesthetics applicable for iontophoretic formulation of the drugs.	2001 May 7	11337149
Safety and pharmacokinetics of EMLA in the treatment of postburn pruritus in pediatric patients: a pilot study.	2001 May-Jun	11403247
Evaluation of pain management interventions for neonatal circumcision pain.	2001 May-Jun	11353359
Efficacy of subcutaneous and topical local anaesthesia for pain relief after resection of malignant breast tumours.	2001 Nov	11848236
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	11808908
Re: reduction in pain associated with open carpal tunnel decompression.	2001 Oct	11560444
Antimicrobial activity of ropivacaine and other local anaesthetics.	2001 Oct	11553246
Clinical and radiographic evaluation of pulpotomies performed under intrapulpal injection of anaesthetic solution.	2001 Sep	11556510
Methemoglobinemia.	2001 Sep	11527852
Treatment of gustatory sweating with botulinum toxin: special aspects.	2001 Sep-Oct	11528273
Noninvasive drug delivery.	2001 Winter	11765687
[Tumescent technique for local anesthesia].	2002 Feb	11865385
Vascular and neural mechanisms of ACh-mediated vasodilation in the forearm cutaneous microcirculation.	2002 Feb	11796692
Local anesthesia with EMLA cream for maxillary sinus puncture.	2002 Jan	11800375
Characteristics of drug substances in oily solutions. Drug release rate, partitioning and solubility.	2002 Jan 31	11790494
Reader questions pain and peritumoral injection.	2002 Jan-Feb	11817487
The use of glyceryl trinitrate ointment with EMLA cream for i.v. cannulation in children undergoing routine surgery.	2002 Jun	12075639

Patents

Sample Use Guides

In Vivo Use Guide

Use the included blunt tipped applicator to apply gel to gingival margins and periodontal pockets

Route of Administration: Dental

In Vitro Use Guide

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

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Name

Type

Language

PROPITOCAINE

Preferred Name

English

PRILOCAINE

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