dibucaine   Click here for help

GtoPdb Ligand ID: 7159

Synonyms: Cincain ® | cincaine chloride | Nupercaine ®
Approved drug
dibucaine is an approved drug
Compound class: Synthetic organic
Comment: Marketed formulations may contain dibucaine hydrochloride (PubChem CID 521951).
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 CDK toolkit. 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 4
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 57.95
Molecular weight 343.23
XLogP 4.64
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCCCOc1nc2ccccc2c(c1)C(=NCCN(CC)CC)O
Isomeric SMILES CCCCOc1nc2ccccc2c(c1)C(=NCCN(CC)CC)O
InChI InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
InChI Key PUFQVTATUTYEAL-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used to produce local or regional anaesthesia (e.g. percutaneous injection, lumbar and epidural procedures and topical application). This drug is approved as dibucaine (USAN) in the US, for topical use, although no approval date is available. The Electronic Medicines Compendium (eMC) only has records for topical medications containing the ingredient cinchocaine (INN) in combination products with anti-inflammatory components that are used to manage pain, irritation and pruritis associated with haemorrhoids and pruritis ani.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This drug inhibits sodium influx through neuronal voltage gated sodium channels. This prevents membrane depolarisation and subsequently blocks initiation and propagation of nerve impulses.