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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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	Inhibitor 8,297
Sodium channel protein type V alpha subunit 49	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614	Preventing		Approved 8,429	ORAQIX

C_max

Value	Dose	Co-administered	Analyte	Population
106 ng/mL	42.5 mg 5 times / 3 hours multiple, buccal	LIDOCAINE	PRILOCAINE plasma	Homo sapiens
0.07 μg/mL	1.5 g single, topical	LIDOCAINE	PRILOCAINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
26000 ng × min/mL	42.5 mg 5 times / 3 hours multiple, buccal	LIDOCAINE	PRILOCAINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.8 h	42.5 mg 5 times / 3 hours multiple, buccal	LIDOCAINE	PRILOCAINE plasma	Homo sapiens
70 min	single, intravenous		PRILOCAINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
45%	1.5 g single, topical	LIDOCAINE	PRILOCAINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
6 mg/kg single, transdermal	unhealthy, 6 years	Other AEs: Methemoglobinemia...

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AEs

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AE	Significance	Dose	Population
Methemoglobinemia		6 mg/kg single, transdermal	unhealthy, 6 years

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Sourcing

Sourcing

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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

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PubMed

Show entries

Title	Date	PubMed
[Comment on the article "Use of EMLA cream and ropivacaine indacryocystorhinostomy with locoregional anesthesia and sedation"].	2001 Apr	11333814
The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing.	2001 Dec	11849260
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
Factors affecting patients' and potential patients' choices among anaesthetics for periodontal recall visits.	2001 Mar	11306158

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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.