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
Use of EMLA cream with vasectomy.	2002-07	12100939
The use of glyceryl trinitrate ointment with EMLA cream for i.v. cannulation in children undergoing routine surgery.	2002-06	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.	2002-06	12042548
Lidocaine iontophoresis versus eutectic mixture of local anesthetics (EMLA) for IV placement in children.	2002-06	12032012
Amethocaine-lidocaine cream, a new topical formulation for preventing venopuncture-induced pain in children.	2002-05-23	12016603
In vitro effects of some anesthetic drugs on enzymatic activity of human red blood cell glucose 6-phosphate dehydrogenase.	2002-05-22	12020046
Reducing venipuncture and intravenous insertion pain with eutectic mixture of local anesthetic: a meta-analysis.	2002-05-02	11984382
Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1.	2002-05	12095024
The effects of age on neural blockade and hemodynamic changes after epidural anesthesia with ropivacaine.	2002-05	11973214
[Management of leg ulcers in the elderly].	2002-04	12046126
Intravenous regional guanethidine blockade in the treatment of post-traumatic complex regional pain syndrome type 1 (algodystrophy) of the hand.	2002-04	12002497
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction.	2002-04	11991536
Lidocaine-prilocaine cream versus tetracaine gel for procedural pain in children.	2002-04	11918521
EMLA cream-induced irritant contact dermatitis.	2002-03	11972719
Topical anesthesia for minor gynecological procedures: a review.	2002-03	11889416
Subcutaneous infusion anesthesia for dermatologic surgery in children: are we ready?	2002-02-14	11841645
Dermatosurgery using subcutaneous infusion anesthesia with prilocaine and ropivacaine in children.	2002-02-14	11841629
Effects of dental local anaesthetics in cardiac transplant recipients.	2002-02-09	11863154
EMLA cream prior to digital nerve block for ingrown nail surgery does not reduce pain at injection of anesthetic solution.	2002-02	11942872
A comparison of prilocaine and lidocaine for intravenous regional anaesthesia for forearm fracture reduction in children.	2002-02	11882226
[Tumescent technique for local anesthesia].	2002-02	11865385
Vascular and neural mechanisms of ACh-mediated vasodilation in the forearm cutaneous microcirculation.	2002-02	11796692
Reader questions pain and peritumoral injection.	2002-01-31	11817487
Characteristics of drug substances in oily solutions. Drug release rate, partitioning and solubility.	2002-01-31	11790494
Evidence that the human cutaneous venoarteriolar response is not mediated by adrenergic mechanisms.	2002-01-15	11790822
Use of negatively charged cyclodextrins for the simultaneous enantioseparation of selected anesthetic drugs by capillary electrophoresis-mass spectrometry.	2002-01-15	11755762
Local anesthesia prior to the insertion of peripherally inserted central catheters.	2002-01-05	11758266
Local anesthesia with EMLA cream for maxillary sinus puncture.	2002-01	11800375
Topical anesthetics update: EMLA and beyond.	2001-12	11849263
The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing.	2001-12	11849260
[Some aspects of epidural anesthesia in patients with chronic renal insufficiency].	2001-11-06	11692688
[Can treatment of flat angiomas be proposed in the first months of life?].	2001-11	11908185
Efficacy of subcutaneous and topical local anaesthesia for pain relief after resection of malignant breast tumours.	2001-11	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.	2001-11	11808908
Blood flow changes in human dental pulps when capsaicin is applied to the adjacent gingival mucosa.	2001-11	11709694
Pain experience during transvaginal aspiration of immature oocytes.	2001-11	11703205
Reflection spectroscopy of analgesized skin.	2001-11	11678641
Quality of anaesthesia for insertion of tension-free vaginal tape using local analgesia and sedation.	2001-11	11580782
[Neurotoxicity of intrathecal lidocaine].	2001-10-10	11591281
Plasma concentrations of lignocaine and prilocaine after a 24-h application of analgesic cream (EMLA) to leg ulcers.	2001-10	11703277
Pain on injection of prilocaine plain vs. lidocaine with epinephrine. A prospective double-blind study.	2001-10	11680354
[New uses of EMLA: anesthesia for relief of pain caused by hemorrhoid thrombosis].	2001-10	11674991
[Ovarian puncture in fertilization in vitro: what analgesia?].	2001-09	11680947
The effect of lidocaine/prilocaine cream on an experimental wound healing model.	2001-09	11587465
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001-08	11895133
Topical anesthetics in children: agents and techniques that equally comfort patients, parents, and clinicians.	2001-08	11717557
1% lidocaine injection, EMLA cream, or "numby stuff" for topical analgesia associated with peripheral intravenous cannulation.	2001-06	11759560
Use of EMLA: is it an injection free alternative?	2001	12049081
[Experiences with liposuction of established surgeons].	2001	11824336
Noninvasive drug delivery.	2001	11765687

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