PRILOCAINE

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 Search

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	( + / - )

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 32 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833	Inhibitor 7701
Sodium channel protein type V alpha subunit 47 Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00750	Inhibitor 7701

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 580 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021451s008lbl.pdf	Preventing		Approved 7997	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

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 n = 1 Health Status: unhealthy Age Group: 6 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Age Group: 6 years Sex: M Population Size: 1 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
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
eMolecules	902352	https://www.emolecules.com/cgi-bin/more?vid=902352

PubMed

Title	Date	PubMed
Prilocaine versus lignocaine for minor lid procedures.	2000 Aug	11040906
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
Topical anesthetics in children: agents and techniques that equally comfort patients, parents, and clinicians.	2001 Aug	11717557
Local anaesthetic block copolymer system undergoing phase transition on dilution with water.	2001 Aug	11457650
[Neurotoxicity of intrathecal lidocaine].	2001 Aug-Sep	11591281
Oral sucrose compares favourably with lidocaine-prilocaine cream for pain relief during venepuncture in neonates.	2001 Feb	11236045
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
[Anesthesia with EMLA cream: a promising application for plastic surgery].	2001 Jun-Jul	11446946
Dermal pharmacokinetics of microemulsion formulations determined by in vivo microdialysis.	2001 Mar	11442278
[Peripheral nerve block. An overview of new developments in an old technique].	2001 May	11417266
[Varicose vein operations with tumescence local anesthesia--an effective method].	2001 May	11383083
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
Blood flow changes in human dental pulps when capsaicin is applied to the adjacent gingival mucosa.	2001 Nov	11709694
Pain experience during transvaginal aspiration of immature oocytes.	2001 Nov	11703205
Quality of anaesthesia for insertion of tension-free vaginal tape using local analgesia and sedation.	2001 Nov	11580782
Dermatosurgery using subcutaneous infusion anesthesia with prilocaine and ropivacaine in children.	2001 Nov-Dec	11841629
Plasma concentrations of lignocaine and prilocaine after a 24-h application of analgesic cream (EMLA) to leg ulcers.	2001 Oct	11703277
[New uses of EMLA: anesthesia for relief of pain caused by hemorrhoid thrombosis].	2001 Oct	11674991
EMLA--1 h is not enough for venous cannulation.	2001 Oct	11576146
EMLA or Ametop, and for how long?	2001 Oct	11576145
Re: reduction in pain associated with open carpal tunnel decompression.	2001 Oct	11560444
Antimicrobial activity of ropivacaine and other local anaesthetics.	2001 Oct	11553246
The effect of lidocaine/prilocaine cream on an experimental wound healing model.	2001 Sep	11587465
Topical anesthesia with or without propofol sedation versus retrobulbar/peribulbar anesthesia for cataract extraction: prospective randomized trial.	2001 Sep	11566518
The efficacy of a range of contact media as coupling agents in extracorporeal shockwave lithotripsy.	2001 Sep	11564013
Clinical and radiographic evaluation of pulpotomies performed under intrapulpal injection of anaesthetic solution.	2001 Sep	11556510
Use of EMLA: is it an injection free alternative?	2001 Spring	12049081
[Management of leg ulcers in the elderly].	2002 Apr	12046126
Vascular and neural mechanisms of ACh-mediated vasodilation in the forearm cutaneous microcirculation.	2002 Feb	11796692
Effects of dental local anaesthetics in cardiac transplant recipients.	2002 Feb 9	11863154
Evidence that the human cutaneous venoarteriolar response is not mediated by adrenergic mechanisms.	2002 Jan 15	11790822
Use of negatively charged cyclodextrins for the simultaneous enantioseparation of selected anesthetic drugs by capillary electrophoresis-mass spectrometry.	2002 Jan 15	11755762
In vitro effects of some anesthetic drugs on enzymatic activity of human red blood cell glucose 6-phosphate dehydrogenase.	2002 Jan-Feb	12020046
The use of glyceryl trinitrate ointment with EMLA cream for i.v. cannulation in children undergoing routine surgery.	2002 Jun	12075639
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	12042548
Lidocaine iontophoresis versus eutectic mixture of local anesthetics (EMLA) for IV placement in children.	2002 Jun	12032012
Topical anesthesia for minor gynecological procedures: a review.	2002 Mar	11889416
Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1.	2002 May	12095024
Amethocaine-lidocaine cream, a new topical formulation for preventing venopuncture-induced pain in children.	2002 May-Jun	12016603

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 `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

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Name

Type

Language

PRILOCAINE

Official Name

English

PRILOCAINE [INN]

Common Name

English

PROPITOCAINE

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