methylphenidate   Click here for help

GtoPdb Ligand ID: 7236

Synonyms: Concerta® | Jornay PM® (a.k.a. HLD200) | Ritalin®
Approved drug
methylphenidate is an approved drug (FDA (1955))
Compound class: Synthetic organic
Comment: Methylphenidate is a racemic mixture of optical isomers (enantiomers). We show the chemical structure without specified stereochemistry to represent the mixture. The most active (R,R) enantiomer is the approved drug dexmethylphenidate. Methylphenidate is administered as the hydrochloride salt (PubChem CID 9280).
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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: methylphenidate

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 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 38.33
Molecular weight 233.14
XLogP 2.5
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 COC(=O)C(c1ccccc1)C1CCCCN1
Isomeric SMILES COC(=O)C(c1ccccc1)C1CCCCN1
InChI InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3
InChI Key DUGOZIWVEXMGBE-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used alongside educational and psychosocial intervention to treat attention deficit hyperactivity disorder (ADHD) and to treat narcolepsy.
An extended release, chewable formulation of methylphenidate hydrochloride (QuilliChew ER) was approved by the US FDA in December 2015. Cotempla XR-ODT, an extended-release orally disintegrating methylphenidate-containing tablet was FDA approved for ADHD in June 2017.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This drug blocks the reuptake of norepinephrine and dopamine into presynaptic neurons, resulting in increased levels of monoamines active in the extraneuronal space. Neurotransmitter reuptake is performed by the transporter proteins SLC6A3 (dopamine) and SLC6A2 (norepinephrine). As these neurotransmitters are involved in maintaining alertness and sustaining thought and motivation this action may underlie the clinical benefits in ADHD. However the full molecular mechanism of action remains to be fully resolved. See the DrugBank link for further details.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com