PRILOCAINE HYDROCHLORIDE

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=C(C)C=CC=C1

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 37 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833	Inhibitor 8297
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00750	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021451s008lbl.pdf	Preventing		Approved 8429	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 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
Pharmacological management of pain and anxiety during emergency procedures in children.	2001	11393327
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
Local anaesthetic block copolymer system undergoing phase transition on dilution with water.	2001 Aug	11457650
[Neurotoxicity of intrathecal lidocaine].	2001 Aug-Sep	11591281
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
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
Intrapocket anesthesia for scaling and root planing: results of a double-blind multicenter trial using lidocaine prilocaine dental gel.	2001 Jul	11495138
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
[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
Dermal pharmacokinetics of microemulsion formulations determined by in vivo microdialysis.	2001 Mar	11442278
[Citanest recalled--bad and inconsistent decision by Astra pharmaceutical company].	2001 Mar 7	11301988
[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
Emla versus ice as a topical anesthetic.	2001 May	11359502
Plasma levels of lidocaine and prilocaine after application of Oraqix, a new intrapocket anesthetic, in patients with advanced periodontitis.	2001 May	11350505
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
Reflection spectroscopy of analgesized skin.	2001 Nov	11678641
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
EMLA--1 h is not enough for venous cannulation.	2001 Oct	11576146
EMLA or Ametop, and for how long?	2001 Oct	11576145
Effect of an intervention to reduce procedural pain and distress for children with HIV infection.	2001 Oct-Nov	11553696
[Ovarian puncture in fertilization in vitro: what analgesia?].	2001 Sep	11680947
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
Methemoglobinemia.	2001 Sep	11527852
Use of EMLA: is it an injection free alternative?	2001 Spring	12049081
Noninvasive drug delivery.	2001 Winter	11765687
The use of EMLA for an intraoral soft-tissue biopsy in a needle phobic: a case report.	2001 Winter	11495404
[Management of leg ulcers in the elderly].	2002 Apr	12046126
A comparison of prilocaine and lidocaine for intravenous regional anaesthesia for forearm fracture reduction in children.	2002 Feb	11882226
[Tumescent technique for local anesthesia].	2002 Feb	11865385
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
In vitro effects of some anesthetic drugs on enzymatic activity of human red blood cell glucose 6-phosphate dehydrogenase.	2002 Jan-Feb	12020046
Reader questions pain and peritumoral injection.	2002 Jan-Feb	11817487
Use of EMLA cream with vasectomy.	2002 Jul	12100939
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
EMLA cream-induced irritant contact dermatitis.	2002 Mar	11972719
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.

Name

Type

Language

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

PROPITOCAINE HYDROCHLORIDE

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