U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of PRILOCAINE HYDROCHLORIDE

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
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

Curator's Comment: Prilocaine crosses the blood-brain and placental barriers

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
106 ng/mL
42.5 mg 5 times / 3 hours multiple, buccal
dose: 42.5 mg
route of administration: Buccal
experiment type: MULTIPLE
co-administered: LIDOCAINE
PRILOCAINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.07 μg/mL
1.5 g single, topical
dose: 1.5 g
route of administration: Topical
experiment type: SINGLE
co-administered: LIDOCAINE
PRILOCAINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
26000 ng × min/mL
42.5 mg 5 times / 3 hours multiple, buccal
dose: 42.5 mg
route of administration: Buccal
experiment type: MULTIPLE
co-administered: LIDOCAINE
PRILOCAINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.8 h
42.5 mg 5 times / 3 hours multiple, buccal
dose: 42.5 mg
route of administration: Buccal
experiment type: MULTIPLE
co-administered: LIDOCAINE
PRILOCAINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
70 min
single, intravenous
PRILOCAINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
1.5 g single, topical
dose: 1.5 g
route of administration: Topical
experiment type: SINGLE
co-administered: LIDOCAINE
PRILOCAINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
6 mg/kg single, transdermal
Dose: 6 mg/kg
Route: transdermal
Route: single
Dose: 6 mg/kg
Sources:
unhealthy, 6 years
n = 1
Health Status: unhealthy
Age Group: 6 years
Sex: M
Population Size: 1
Sources:
Other AEs: Methemoglobinemia...
Other AEs:
Methemoglobinemia
Sources:
AEs

AEs

AESignificanceDosePopulation
Methemoglobinemia
6 mg/kg single, transdermal
Dose: 6 mg/kg
Route: transdermal
Route: single
Dose: 6 mg/kg
Sources:
unhealthy, 6 years
n = 1
Health Status: unhealthy
Age Group: 6 years
Sex: M
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Pharmacological management of pain and anxiety during emergency procedures in children.
2001
A randomised, double-blind, placebo-controlled, comparative study of topical skin analgesics and the anxiety and discomfort associated with venous cannulation.
2001 Apr 28
Local anaesthetic block copolymer system undergoing phase transition on dilution with water.
2001 Aug
[Neurotoxicity of intrathecal lidocaine].
2001 Aug-Sep
Topical anesthetics update: EMLA and beyond.
2001 Dec
The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing.
2001 Dec
Hyperpigmentation following the use of Emla cream.
2001 Jan
Comparison of topical EMLA 5% oral adhesive to benzocaine 20% on the pain experienced during palatal anesthetic infiltration in children.
2001 Jan-Feb
Intrapocket anesthesia for scaling and root planing: results of a double-blind multicenter trial using lidocaine prilocaine dental gel.
2001 Jul
A comparison of 1% prilocaine with 0.5% ropivacaine for outpatient-based surgery under axillary brachial plexus block.
2001 Jul
Effects of prilocaine and articaine on human leucocytes and reactive oxygen species in vitro.
2001 Jul
[Some aspects of epidural anesthesia in patients with chronic renal insufficiency].
2001 Jul-Aug
Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells.
2001 Jun 15
Dermal pharmacokinetics of microemulsion formulations determined by in vivo microdialysis.
2001 Mar
[Citanest recalled--bad and inconsistent decision by Astra pharmaceutical company].
2001 Mar 7
[Peripheral nerve block. An overview of new developments in an old technique].
2001 May
[Varicose vein operations with tumescence local anesthesia--an effective method].
2001 May
Emla versus ice as a topical anesthetic.
2001 May
Plasma levels of lidocaine and prilocaine after application of Oraqix, a new intrapocket anesthetic, in patients with advanced periodontitis.
2001 May
Safety and pharmacokinetics of EMLA in the treatment of postburn pruritus in pediatric patients: a pilot study.
2001 May-Jun
Evaluation of pain management interventions for neonatal circumcision pain.
2001 May-Jun
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
Reflection spectroscopy of analgesized skin.
2001 Nov
Pain on injection of prilocaine plain vs. lidocaine with epinephrine. A prospective double-blind study.
2001 Oct
[New uses of EMLA: anesthesia for relief of pain caused by hemorrhoid thrombosis].
2001 Oct
EMLA--1 h is not enough for venous cannulation.
2001 Oct
EMLA or Ametop, and for how long?
2001 Oct
Effect of an intervention to reduce procedural pain and distress for children with HIV infection.
2001 Oct-Nov
[Ovarian puncture in fertilization in vitro: what analgesia?].
2001 Sep
Topical anesthesia with or without propofol sedation versus retrobulbar/peribulbar anesthesia for cataract extraction: prospective randomized trial.
2001 Sep
The efficacy of a range of contact media as coupling agents in extracorporeal shockwave lithotripsy.
2001 Sep
Clinical and radiographic evaluation of pulpotomies performed under intrapulpal injection of anaesthetic solution.
2001 Sep
Methemoglobinemia.
2001 Sep
Use of EMLA: is it an injection free alternative?
2001 Spring
Noninvasive drug delivery.
2001 Winter
The use of EMLA for an intraoral soft-tissue biopsy in a needle phobic: a case report.
2001 Winter
[Management of leg ulcers in the elderly].
2002 Apr
A comparison of prilocaine and lidocaine for intravenous regional anaesthesia for forearm fracture reduction in children.
2002 Feb
[Tumescent technique for local anesthesia].
2002 Feb
Effects of dental local anaesthetics in cardiac transplant recipients.
2002 Feb 9
Evidence that the human cutaneous venoarteriolar response is not mediated by adrenergic mechanisms.
2002 Jan 15
In vitro effects of some anesthetic drugs on enzymatic activity of human red blood cell glucose 6-phosphate dehydrogenase.
2002 Jan-Feb
Reader questions pain and peritumoral injection.
2002 Jan-Feb
Use of EMLA cream with vasectomy.
2002 Jul
The use of glyceryl trinitrate ointment with EMLA cream for i.v. cannulation in children undergoing routine surgery.
2002 Jun
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
Lidocaine iontophoresis versus eutectic mixture of local anesthetics (EMLA) for IV placement in children.
2002 Jun
EMLA cream-induced irritant contact dermatitis.
2002 Mar
Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1.
2002 May
Amethocaine-lidocaine cream, a new topical formulation for preventing venopuncture-induced pain in children.
2002 May-Jun
Patents

Sample Use Guides

Use the included blunt tipped applicator to apply gel to gingival margins and periodontal pockets
Route of Administration: Dental
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
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
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
JAN  
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
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID2031956
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
FDA UNII
MJW015BAPH
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL1194
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
DRUG BANK
DBSALT000962
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
PUBCHEM
92163
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
DAILYMED
MJW015BAPH
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
CHEBI
32053
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
217-244-0
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
MERCK INDEX
m9132
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY Merck Index
CAS
1786-81-8
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
RS_ITEM_NUM
1561008
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
EVMPD
SUB04038MIG
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
NCI_THESAURUS
C48012
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
SMS_ID
100000085080
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
NSC
758432
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY
RXCUI
2557
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
PRIMARY RxNorm
CAS
88208-29-1
Created by admin on Fri Dec 15 15:35:12 GMT 2023 , Edited by admin on Fri Dec 15 15:35:12 GMT 2023
SUPERSEDED