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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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Click here for structure editor
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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1965)
IUPAC Name Click here for help
N-(2-methylphenyl)-2-(propylamino)propanimidic acid
International Nonproprietary Names Click here for help
INN number INN
1641 prilocaine
Synonyms Click here for help
ASTRA 1512 | L-67 | Prilotekal®
Database Links Click here for help
CAS Registry No. 721-50-6
ChEMBL Ligand CHEMBL1194
DrugBank Ligand DB00750
DrugCentral Ligand 2265
GtoPdb PubChem SID 178103850
PubChem CID 4906
Search Google for chemical match using the InChIKey MVFGUOIZUNYYSO-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MVFGUOIZUNYYSO
Search PubMed clinical trials prilocaine
Search PubMed titles prilocaine
Search PubMed titles/abstracts prilocaine
UniChem Compound Search for chemical match using the InChIKey MVFGUOIZUNYYSO-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MVFGUOIZUNYYSO-UHFFFAOYSA-N
Wikipedia Prilocaine

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Prilocaine (links to external site)
Cat. No. HY-B0137