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).

dibucaine is commercially available from our sponsors

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 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

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 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

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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboximidic acid
International Nonproprietary Names Click here for help
INN number INN
108 cinchocaine
Synonyms Click here for help
Cincain ® | cincaine chloride | Nupercaine ®
Database Links Click here for help
CAS Registry No. 85-79-0
ChEMBL Ligand CHEMBL1086
DrugBank Ligand DB00527
DrugCentral Ligand 859
GtoPdb PubChem SID 178103734
PubChem CID 3025
Search Google for chemical match using the InChIKey PUFQVTATUTYEAL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PUFQVTATUTYEAL
Search PubMed clinical trials cinchocaine
Search PubMed titles cinchocaine
Search PubMed titles/abstracts cinchocaine
UniChem Compound Search for chemical match using the InChIKey PUFQVTATUTYEAL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PUFQVTATUTYEAL-UHFFFAOYSA-N
Wikipedia Dibucaine

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MedChemExpress
Dibucaine (links to external site)
Cat. No. HY-B0552