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

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 of PRILOCAINE

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 ( + / - )

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

1.07170562E12
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
From cocaine to ropivacaine: the history of local anesthetic drugs.
2001 Aug
Local anaesthetic block copolymer system undergoing phase transition on dilution with water.
2001 Aug
[Neurotoxicity of intrathecal lidocaine].
2001 Aug-Sep
The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing.
2001 Dec
Intrapocket anesthesia for scaling and root planing: results of a double-blind multicenter trial using lidocaine prilocaine dental gel.
2001 Jul
[Percutaneous topical anaesthesia applications in ocular surgery].
2001 Jul
A comparison of 1% prilocaine with 0.5% ropivacaine for outpatient-based surgery under axillary brachial plexus block.
2001 Jul
Hot chili, a cook and EMLA.
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
1% lidocaine injection, EMLA cream, or "numby stuff" for topical analgesia associated with peripheral intravenous cannulation.
2001 Jun
Eutectic mixture of local anesthetics reduces pain during intravenous catheter insertion in the pediatric patient.
2001 Jun
Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells.
2001 Jun 15
[Anesthesia with EMLA cream: a promising application for plastic surgery].
2001 Jun-Jul
Dermal pharmacokinetics of microemulsion formulations determined by in vivo microdialysis.
2001 Mar
[Peripheral nerve block. An overview of new developments in an old technique].
2001 May
Safety and pharmacokinetics of EMLA in the treatment of postburn pruritus in pediatric patients: a pilot study.
2001 May-Jun
[Can treatment of flat angiomas be proposed in the first months of life?].
2001 Nov
Efficacy of subcutaneous and topical local anaesthesia for pain relief after resection of malignant breast tumours.
2001 Nov
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
Blood flow changes in human dental pulps when capsaicin is applied to the adjacent gingival mucosa.
2001 Nov
Plasma concentrations of lignocaine and prilocaine after a 24-h application of analgesic cream (EMLA) to leg ulcers.
2001 Oct
Pain on injection of prilocaine plain vs. lidocaine with epinephrine. A prospective double-blind study.
2001 Oct
Re: reduction in pain associated with open carpal tunnel decompression.
2001 Oct
Antimicrobial activity of ropivacaine and other local anaesthetics.
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
Methemoglobinemia.
2001 Sep
EMLA versus nitrous oxide for venous cannulation in children.
2001 Sep
Treatment of gustatory sweating with botulinum toxin: special aspects.
2001 Sep-Oct
Noninvasive drug delivery.
2001 Winter
The use of EMLA for an intraoral soft-tissue biopsy in a needle phobic: a case report.
2001 Winter
Intravenous regional guanethidine blockade in the treatment of post-traumatic complex regional pain syndrome type 1 (algodystrophy) of the hand.
2002 Apr
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction.
2002 Apr
Lidocaine-prilocaine cream versus tetracaine gel for procedural pain in children.
2002 Apr
EMLA cream prior to digital nerve block for ingrown nail surgery does not reduce pain at injection of anesthetic solution.
2002 Feb
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
Local anesthesia with EMLA cream for maxillary sinus puncture.
2002 Jan
Use of negatively charged cyclodextrins for the simultaneous enantioseparation of selected anesthetic drugs by capillary electrophoresis-mass spectrometry.
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
Lidocaine iontophoresis versus eutectic mixture of local anesthetics (EMLA) for IV placement in children.
2002 Jun
EMLA cream-induced irritant contact dermatitis.
2002 Mar
Reducing venipuncture and intravenous insertion pain with eutectic mixture of local anesthetic: a meta-analysis.
2002 Mar-Apr
Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1.
2002 May
The effects of age on neural blockade and hemodynamic changes after epidural anesthesia with ropivacaine.
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.
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
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
prilocaine [INN]
Common Name English
PROPITOCAINE
JAN  
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
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
EMA ASSESSMENT REPORTS FORTACIN (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
WHO-ATC N01BB54
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
NDF-RT N0000175682
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
WHO-VATC QN01BB54
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
WHO-ATC N01BB04
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
NDF-RT N0000175976
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
NDF-RT N0000007681
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
EMA ASSESSMENT REPORTS PRILOCAINE (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
NCI_THESAURUS C245
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
Code System Code Type Description
WIKIPEDIA
PRILOCAINE
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
DRUG BANK
DB00750
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
MERCK INDEX
M9132
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY Merck Index
INN
1641
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
LACTMED
Prilocaine
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
EPA CompTox
DTXSID7031955
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
FDA UNII
046O35D44R
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
PUBCHEM
4906
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
RS_ITEM_NUM
1560990
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
NSC
40027
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
IUPHAR
7276
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
ECHA (EC/EINECS)
211-957-0
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
CAS
17676-07-2
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
SUPERSEDED
CHEBI
8404
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
HSDB
3386
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
NCI_THESAURUS
C47685
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
MESH
D011318
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
EVMPD
SUB10041MIG
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
ChEMBL
CHEMBL1194
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
DAILYMED
046O35D44R
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
DRUG CENTRAL
2265
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
USAN
JJ-23
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
RXCUI
8686
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY RxNorm
CAS
721-50-6
Created by admin on Sat Dec 17 02:00:41 UTC 2022 , Edited by admin on Sat Dec 17 02:00:41 UTC 2022
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
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BASIS OF STRENGTH->SUBSTANCE
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