PRILOCAINE HYDROCHLORIDE

First approved in 1965

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H20N2O.ClH
Molecular Weight	256.772
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCCNC(C)C(=O)NC1=CC=CC=C1C

InChI

InChIKey=BJPJNTKRKALCPP-UHFFFAOYSA-N

InChI=1S/C13H20N2O.ClH/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);1H

HIDE SMILES / InChI

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
[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
[Comment on the article "Use of EMLA cream and ropivacaine indacryocystorhinostomy with locoregional anesthesia and sedation"].	2001 Apr	11333814
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
Topical anesthetics update: EMLA and beyond.	2001 Dec	11849263
The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing.	2001 Dec	11849260
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
Comparison of topical EMLA 5% oral adhesive to benzocaine 20% on the pain experienced during palatal anesthetic infiltration in children.	2001 Jan-Feb	11242723
[Some aspects of epidural anesthesia in patients with chronic renal insufficiency].	2001 Jul-Aug	11692688
Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells.	2001 Jun 15	11403930
Factors affecting patients' and potential patients' choices among anaesthetics for periodontal recall visits.	2001 Mar	11306158
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
[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
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
Pain experience during transvaginal aspiration of immature oocytes.	2001 Nov	11703205
Reflection spectroscopy of analgesized skin.	2001 Nov	11678641
Subcutaneous infusion anesthesia for dermatologic surgery in children: are we ready?	2001 Nov-Dec	11841645
Pain on injection of prilocaine plain vs. lidocaine with epinephrine. A prospective double-blind study.	2001 Oct	11680354
[New uses of EMLA: anesthesia for relief of pain caused by hemorrhoid thrombosis].	2001 Oct	11674991
Re: reduction in pain associated with open carpal tunnel decompression.	2001 Oct	11560444
[Ovarian puncture in fertilization in vitro: what analgesia?].	2001 Sep	11680947
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
Methemoglobinemia.	2001 Sep	11527852
Intravenous regional guanethidine blockade in the treatment of post-traumatic complex regional pain syndrome type 1 (algodystrophy) of the hand.	2002 Apr	12002497
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction.	2002 Apr	11991536
[Tumescent technique for local anesthesia].	2002 Feb	11865385
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
Local anesthesia with EMLA cream for maxillary sinus puncture.	2002 Jan	11800375
Evidence that the human cutaneous venoarteriolar response is not mediated by adrenergic mechanisms.	2002 Jan 15	11790822
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
Use of EMLA cream with vasectomy.	2002 Jul	12100939
EMLA cream-induced irritant contact dermatitis.	2002 Mar	11972719
Reducing venipuncture and intravenous insertion pain with eutectic mixture of local anesthetic: a meta-analysis.	2002 Mar-Apr	11984382
The effects of age on neural blockade and hemodynamic changes after epidural anesthesia with ropivacaine.	2002 May	11973214
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.

Name

Type

Language

PROPITOCAINE HYDROCHLORIDE

Preferred Name

English

PRILOCAINE HYDROCHLORIDE

Official Name

English

PRILOCAINE HYDROCHLORIDE [MART.]

Common Name

English

PROPANAMIDE, N-(2-METHYLPHENYL)-2-(PROPYLAMINO)-, HYDROCHLORIDE (1:1)

Systematic Name

English

NSC-758432

Code

English

PROPANAMIDE, N-(2-METHYLPHENYL)-2-(PROPYLAMINO)-, MONOHYDROCHLORIDE

Common Name

English

PRILOCAINE HYDROCHLORIDE [USAN]

Common Name

English

PRILOCAINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

XYLONEST

Brand Name

English

PRILOCAINE HYDROCHLORIDE [MI]

Common Name

English

CITANEST PLAIN

Brand Name

English

L-67

Code

English

CITANEST HYDROCHLORIDE

Brand Name

English

PRILOCAINE HYDROCHLORIDE [EP IMPURITY]

Common Name

English

PRILOCAINE HCL

Common Name

English

L-67 HYDROCHLORIDE

Code

English

PRILOCAINE HYDROCHLORIDE [VANDF]

Common Name

English

ASTRA 1512

Code

English

PRILOCAINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

Prilocaine hydrochloride [WHO-DD]

Common Name

English

PRILOCAINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

PROPITOCAINE HYDROCHLORIDE [JAN]

Common Name

English

CITANEST

Brand Name

English

PRILOCAINE HYDROCHLORIDE [USP-RS]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245