ropivacaine   Click here for help

GtoPdb Ligand ID: 7602

Synonyms: 1-propyl-2',6'-pipecoloxylidide | AL-381 | LEA-103 | Naropin® | ropivacaine hydrochloride
Approved drug
ropivacaine is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Ropivacaine is an amino amide local anaesthetic. We show the (S) enantiomer here, but the name can also be used to refer to the racemic mixture of optical isomers.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: ropivacaine

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 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 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 32.34
Molecular weight 274.2
XLogP 3
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 CCCN1CCCCC1C(=O)Nc1c(C)cccc1C
Isomeric SMILES CCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
InChI InChI=1S/C17H26N2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20)/t15-/m0/s1
InChI Key ZKMNUMMKYBVTFN-HNNXBMFYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
IUPAC Name Click here for help
(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
5376 ropivacaine
Synonyms Click here for help
1-propyl-2',6'-pipecoloxylidide | AL-381 | LEA-103 | Naropin® | ropivacaine hydrochloride
Database Links Click here for help
CAS Registry No. 84057-95-4
ChEBI CHEBI:8890
ChEMBL Ligand CHEMBL1077896
DrugBank Ligand DB00296
DrugCentral Ligand 2403
GtoPdb PubChem SID 223365937
PubChem CID 175805
Search Google for chemical match using the InChIKey ZKMNUMMKYBVTFN-HNNXBMFYSA-N
Search Google for chemicals with the same backbone ZKMNUMMKYBVTFN
Search PubMed clinical trials ropivacaine
Search PubMed titles ropivacaine
Search PubMed titles/abstracts ropivacaine
UniChem Compound Search for chemical match using the InChIKey ZKMNUMMKYBVTFN-HNNXBMFYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZKMNUMMKYBVTFN-HNNXBMFYSA-N
Wikipedia Ropivacaine