Compound: Lisdexamfetamine
SMILES: O=C(N[C@H](Cc1ccccc1)C)[C@@H](N)CCCCN
InChIKey: VOBHXZCDAVEXEY-JSGCOSHPSA-N
Synonyms: Lisdexamfetamine, lisdexamphetamine, 608137-32-2, L-lysine-d-amphetamine, H645GUL8KJ, lisdexanfetamina, L-lysine-dextroamphetamine, (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide, (2S)-2,6-Diamino-N-((1S)-1-methyl-2-phenylethyl)hexanamide, DTXSID00209652, (2S)-2,6-Diamino-N-[(1S)-1-methyl-2-phenylethyl]hexanamide, (2S)-2,6-diamino-N-((2S)-1-phenylpropan-2-yl)hexanamide, lisdexamfetaminum, (2S)-2,6-diamino-N-((2S)-1-phenylpropan-2-yl)hexanimidic acid, (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanimidic acid, RefChem:5951, DTXCID50132143, N06BA12, Lisdexamfetamine [INN], UNII-H645GUL8KJ, Lisdexamfetamine (INN), HSDB 8277, LISDEXAMFETAMINE [MI], SCHEMBL158949, GTPL7213, LISDEXAMFETAMINE [VANDF], CHEMBL1201222, LISDEXAMFETAMINE [WHO-DD], CHEBI:135925, DB01255, NS00017968, N-[(2S)-1-Phenylpropan-2-yl]-L-lysinamide, D08130, N-[(1S)-1-Methyl-2-phenylethyl]-L-lysinamide, Q6558704, Hexanamide, 2,6-diamino-N-[(1S)-1-methyl-2-phenylethyl]-, (2S)-
Theoretical properties:
molecular_formula: C15H25N3O
molecular_weight: 263.38 g/mol
exact_mass: 263.199762429 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 8
heavy_atom_count: 19
topological_polar_surface_area: 81.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Golden-colored solid from methanol
color: Golden-colored solid from methanol
melting_point: 191-193
flash_point: 9.7 °C; 49.5 °F (closed cup)
Descriptions:
pubchem: Lisdexamfetamine is an amino acid amide.
chembl: LISDEXAMFETAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Lisdexamfetamine, sold under the brand names Vyvanse (, VY-vans) and Elvanse among others, is a stimulant medication that is used as a treatment for attention deficit hyperactivity disorder (ADHD) in both children and adults, and for moderate-to-severe binge eating disorder in adults. A prodrug of dextroamphetamine, lisdexamfetamine is taken by mouth. Its effects generally begin within 90 minutes and last for up to 14 hours.
Common side effects of lisdexamfetamine include loss of appetite, anxiety, diarrhea, trouble sleeping, irritability, and nausea. Rare but serious side effects include mania, sudden cardiac death in those with underlying heart problems, and psychosis. It has a high potential for substance abuse. Serotonin syndrome may occur if used with certain other medications. Its use during pregnancy may result in harm to the fetus, and use during breastfeeding is not recommended by the manufacturer as dextroamphetamine (its metabolite) can pass through the breastmilk.
Lisdexamfetamine is an inactive prodrug that is formed by the condensation of L-lysine, a naturally occurring amino acid, and dextroamphetamine. In the body, metabolic action reverses this process to release the active agent, the central nervous system (CNS) stimulant dextroamphetamine.
Lisdexamfetamine was approved for medical use in the United States in 2007 and in the European Union in 2012. In 2023, it was the 76th most commonly prescribed medication in the United States, with more than 9 million prescriptions. It is a Class B controlled substance in the United Kingdom, a Schedule 8 controlled drug in Australia, and a Schedule II controlled substance in the United States.