lisdexamfetamine   Click here for help

GtoPdb Ligand ID: 7213

Synonyms: NRP104 | Vyvanse®
Approved drug
lisdexamfetamine is an approved drug (FDA (2007))
Compound class: Synthetic organic
Comment: This drug is a prodrug of dexamphetamine. The amphetamine is released more slowly from this prodrug than by administering active amphetamine directly.
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 3
Rotatable bonds 8
Topological polar surface area 84.63
Molecular weight 263.2
XLogP 1.82
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 NCCCCC(C(=NC(Cc1ccccc1)C)O)N
Isomeric SMILES NCCCC[C@@H](C(=N[C@H](Cc1ccccc1)C)O)N
InChI InChI=1S/C15H25N3O/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19)/t12-,14-/m0/s1
InChI Key VOBHXZCDAVEXEY-JSGCOSHPSA-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/)
No information available.
Summary of Clinical Use Click here for help
Lisdexamfetamine is used to treat attention deficit hyperactivity disorder (ADHD) in combination with educational and psychosocial intervention. In February 2015, the US FDA expanded approval to include the treatment of binge-eating disorder.
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. 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