CAS 721-50-6|CAS 1786-81-8|prilocaine|Prilocaine|N-(2-methylphenyl)-2-(propylamino)propanamide|Propitocaine|Astra 1512|Citanest Plain|Citanest|Astra 1515|N-[2-Methylphenyl]-2-[propylamino]propanamid...

General Information

Structure

Molecular Formula

C₁₃H₂₀N₂O

Molecular Mass

220.3107

Exact Mass

220.15756327

Charge

InChI

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)

InChIKey

MVFGUOIZUNYYSO-UHFFFAOYSA-N

Canonic Smiles

CCCNC(C(=O)Nc1ccccc1C)C

Isomeric Smiles

O=C(Nc1c(cccc1)C)C(NCCC)C

Calculated Properties

JChem

LogD (pH = 7.4)

1.25

LogD (pH = 5.5)

-0.30

Log P

2.68

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.82

Polar Surface Area

41.13

Polarizability

25.58

Molar Refractivity

67.86

LOG S

-2.68

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC name

N-(2-methylphenyl)-2-(propylamino)propanamide

Synonyms

PrilocaineN-[2-Methylphenyl]-2-[propylamino]propanamidePRILOCAINE HYDROCHLORIDEalpha-n-Propylamino-2-methylpropionanilide2-(Propylamino)-o-propionotoluidideo-Methyl-alpha-propylaminopropionanilideo-Methyl-2-propylaminopropionanilideN-(2-Methylphenyl)-2-(propylamino)propanamide2-Methyl-alpha-propylaminopropionanilidePropitocaineprilocaineprilocaine base

IUPAC Traditional name

prilocaine

Brand Name

PropitocaineCitanestAstra 1512Astra 1515Citanest Plain

API Name

Prilocaine

International Nonproprietary Name (INN)

prilocainaprilocainum

Names and Identifiers

Registration numbers

CAS Number

721-50-61786-81-8

PubChem CID

4906

PubChem SID

4650506616096409392729955

EC Number

217-244-0

DrugBank ID

DB00750

PubMed Citation Links

2619976499897962635649026049614

MetaboLights Database

MTBLS4967MTBLS1693MTBLS3750MTBLS2145MTBLS2406MTBLS1642

CHEBI ID

CHEBI:308749CHEBI:8404

Beilstein Number

BRENDA Database

CHEMBL

KEGG DRUG Database

Wikipedia Title

Drug Central Database

2,265

Patent number

GB839943US3160662

BRENDA Ligand Database

SureChEMBL Database

LINCS Database

BKMS React Database

KEGG ID

CompTox Database

ACToR Database

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.1

Solubility

541 mg/L

Melting Point

167-168°C

Safety Information

Storage Condition

-20°C

Room Temperature (15-30°C)

MSDS Link

Download link

RTECS

UG5775000

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00750

Drug Groups

approved

Description

A local anesthetic that is similar pharmacologically to lidocaine. Currently, it is used most often for infiltration anesthesia in dentistry. (From AMA Drug Evaluations Annual, 1992, p165)

Indication

Used as a local anaesthetic and is often used in dentistry.

Pharmacology

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.

Affected Organisms

Humans and other mammals

Protein Binding

98%

Elimination

Prilocaine is metabolized in both the liver and the kidney and excreted via the kidney.

External Links

• [Wikipedia]

Selleck Chemicals

S1619

Research Area: Neurological Disease
Biological Activity:
Prilocaine is a local anesthetic of the amino amide type. It is often used in dentistry. It is also often combined with lidocaine as a preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia. As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA). [1]

Hydrochloride

An amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Prilocaine

References