prilocaine   Click here for help

GtoPdb Ligand ID: 7276

Synonyms: ASTRA 1512 | L-67 | Prilotekal®
Approved drug
prilocaine is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Prilocaine is often an active ingredient in fixed-mixture medications along with lidocaine.
Marketed formulations may contain prilocaine hydrochloride (PubChem CID 92163).
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 44.62
Molecular weight 220.16
XLogP 2.4
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCNC(C(=Nc1ccccc1C)O)C
Isomeric SMILES CCCNC(C(=Nc1ccccc1C)O)C
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)
InChI Key MVFGUOIZUNYYSO-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Prilocaine is a local anesthetic used commonly in dental practice, administered parenterally by injection to induce nerve block. This drug may also be used to induce spinal anaesthesia for short term surgical procedures.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Prilocaine blocks sodium channels located on neuronal membranes and thereby inhibits action potential and nerve signal propagation. The genes and proteins SNC1A-SNC11A are listed in this database in the voltage-gated sodium channels section.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com