PRILOCAINE

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=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	( + / - )

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 35 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833	Inhibitor 8146
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00750	Inhibitor 8146

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 607 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021451s008lbl.pdf	Preventing		Approved 8307	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
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
[Neurotoxicity of intrathecal lidocaine].	2001 Aug-Sep	11591281
The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing.	2001 Dec	11849260
Intrapocket anesthesia for scaling and root planing: results of a double-blind multicenter trial using lidocaine prilocaine dental gel.	2001 Jul	11495138
[Percutaneous topical anaesthesia applications in ocular surgery].	2001 Jul	11438881
A comparison of 1% prilocaine with 0.5% ropivacaine for outpatient-based surgery under axillary brachial plexus block.	2001 Jul	11429363
Hot chili, a cook and EMLA.	2001 Jul	11421844
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
1% lidocaine injection, EMLA cream, or "numby stuff" for topical analgesia associated with peripheral intravenous cannulation.	2001 Jun	11759560
Eutectic mixture of local anesthetics reduces pain during intravenous catheter insertion in the pediatric patient.	2001 Jun	11444712
Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells.	2001 Jun 15	11403930
[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
Safety and pharmacokinetics of EMLA in the treatment of postburn pruritus in pediatric patients: a pilot study.	2001 May-Jun	11403247
[Can treatment of flat angiomas be proposed in the first months of life?].	2001 Nov	11908185
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
Blood flow changes in human dental pulps when capsaicin is applied to the adjacent gingival mucosa.	2001 Nov	11709694
Plasma concentrations of lignocaine and prilocaine after a 24-h application of analgesic cream (EMLA) to leg ulcers.	2001 Oct	11703277
Pain on injection of prilocaine plain vs. lidocaine with epinephrine. A prospective double-blind study.	2001 Oct	11680354
Re: reduction in pain associated with open carpal tunnel decompression.	2001 Oct	11560444
Antimicrobial activity of ropivacaine and other local anaesthetics.	2001 Oct	11553246
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
Methemoglobinemia.	2001 Sep	11527852
EMLA versus nitrous oxide for venous cannulation in children.	2001 Sep	11524323
Treatment of gustatory sweating with botulinum toxin: special aspects.	2001 Sep-Oct	11528273
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
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
Lidocaine-prilocaine cream versus tetracaine gel for procedural pain in children.	2002 Apr	11918521
EMLA cream prior to digital nerve block for ingrown nail surgery does not reduce pain at injection of anesthetic solution.	2002 Feb	11942872
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
Local anesthesia with EMLA cream for maxillary sinus puncture.	2002 Jan	11800375
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
Reader questions pain and peritumoral injection.	2002 Jan-Feb	11817487
Use of EMLA cream with vasectomy.	2002 Jul	12100939
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
Reducing venipuncture and intravenous insertion pain with eutectic mixture of local anesthetic: a meta-analysis.	2002 Mar-Apr	11984382
Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1.	2002 May	12095024
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 17 02:00:40 UTC 2022` Edited by `admin` on `Sat Dec 17 02:00:40 UTC 2022`
Record UNII	046O35D44R
Record Status	`Validated (UNII)`
Record Version

Download

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 [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