PRILOCAINE HYDROCHLORIDE

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 Search

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

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 37 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833	Inhibitor 8297
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00750	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021451s008lbl.pdf	Preventing		Approved 8429	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 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
[Experiences with liposuction of established surgeons].	2001	11824336
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001 Aug	11895133
Topical anesthetics in children: agents and techniques that equally comfort patients, parents, and clinicians.	2001 Aug	11717557
[Neurotoxicity of intrathecal lidocaine].	2001 Aug-Sep	11591281
Topical anesthetics update: EMLA and beyond.	2001 Dec	11849263
The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing.	2001 Dec	11849260
[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
[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
Pain experience during transvaginal aspiration of immature oocytes.	2001 Nov	11703205
Reflection spectroscopy of analgesized skin.	2001 Nov	11678641
Quality of anaesthesia for insertion of tension-free vaginal tape using local analgesia and sedation.	2001 Nov	11580782
Subcutaneous infusion anesthesia for dermatologic surgery in children: are we ready?	2001 Nov-Dec	11841645
Dermatosurgery using subcutaneous infusion anesthesia with prilocaine and ropivacaine in children.	2001 Nov-Dec	11841629
Local anesthesia prior to the insertion of peripherally inserted central catheters.	2001 Nov-Dec	11758266
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
[New uses of EMLA: anesthesia for relief of pain caused by hemorrhoid thrombosis].	2001 Oct	11674991
[Ovarian puncture in fertilization in vitro: what analgesia?].	2001 Sep	11680947
The effect of lidocaine/prilocaine cream on an experimental wound healing model.	2001 Sep	11587465
Use of EMLA: is it an injection free alternative?	2001 Spring	12049081
Noninvasive drug delivery.	2001 Winter	11765687
[Management of leg ulcers in the elderly].	2002 Apr	12046126
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
Vascular and neural mechanisms of ACh-mediated vasodilation in the forearm cutaneous microcirculation.	2002 Feb	11796692
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
Evidence that the human cutaneous venoarteriolar response is not mediated by adrenergic mechanisms.	2002 Jan 15	11790822
Use of negatively charged cyclodextrins for the simultaneous enantioseparation of selected anesthetic drugs by capillary electrophoresis-mass spectrometry.	2002 Jan 15	11755762
Characteristics of drug substances in oily solutions. Drug release rate, partitioning and solubility.	2002 Jan 31	11790494
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
The use of glyceryl trinitrate ointment with EMLA cream for i.v. cannulation in children undergoing routine surgery.	2002 Jun	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 Jun	12042548
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
Topical anesthesia for minor gynecological procedures: a review.	2002 Mar	11889416
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.

Name

Type

Language

PRILOCAINE HYDROCHLORIDE

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

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