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proparacaine   Click here for help

GtoPdb Ligand ID: 7283

Synonyms: Alcaine® | Paracaine® | proparacaine hydrochloride | proxymetacaine hydrochloride
Approved drug
proparacaine is an approved drug (FDA (1953))
Compound class: Synthetic organic
Comment: Proparacaine is a topical anesthetic drug.
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 64.79
Molecular weight 294.19
XLogP 2.54
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 CCCOc1ccc(cc1N)C(=O)OCCN(CC)CC
Isomeric SMILES CCCOc1ccc(cc1N)C(=O)OCCN(CC)CC
InChI InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
InChI Key KCLANYCVBBTKTO-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. US FDA (1953)
IUPAC Name Click here for help
2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
International Nonproprietary Names Click here for help
INN number INN
540 proxymetacaine
Synonyms Click here for help
Alcaine® | Paracaine® | proparacaine hydrochloride | proxymetacaine hydrochloride
Database Links Click here for help
CAS Registry No. 499-67-2
ChEMBL Ligand CHEMBL1196
DrugBank Ligand DB00807
DrugCentral Ligand 2294
GtoPdb PubChem SID 178103857
PubChem CID 4935
Search Google for chemical match using the InChIKey KCLANYCVBBTKTO-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KCLANYCVBBTKTO
Search PubMed clinical trials proxymetacaine
Search PubMed titles proxymetacaine
Search PubMed titles/abstracts proxymetacaine
UniChem Compound Search for chemical match using the InChIKey KCLANYCVBBTKTO-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KCLANYCVBBTKTO-UHFFFAOYSA-N
Wikipedia Proxymetacaine