Lisdexamfetamine

Lisdexamfetamine
Clinical data
Trade names	Vyvanse, Elvanse, Tyvense, others
Other names	L-Lysine-d-amphetamine; (2S)-2,6-Diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide; N-[(2S)-1-Phenyl-2-propanyl]-L-lysinamide
AHFS/Drugs.com	Monograph
MedlinePlus	a607047
License data	US DailyMed: Lisdexamfetamine;
Pregnancy; category	AU: B3; ;
Dependence; liability	Moderate
Addiction; liability	Moderate
Routes of; administration	By mouth
ATC code	N06BA12 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A3 (Psychoactive drugs); CA: Controlled Drug (CDSA I); DE: Anlage III (Special prescription form required); NZ: Class B; UK: Class B; US: Schedule II; EU: Rx-only; SE: Förteckning II;
Pharmacokinetic data
Bioavailability	Oral: 96.4%
Protein binding	20% (as dextroamphetamine)
Metabolism	Hydrolysis by enzymes in red blood cells initially, subsequent metabolism follows
Metabolites	Dextroamphetamine (and its metabolites) and L-lysine
Onset of action	Oral: <2 hours
Elimination half-life	Lisdexamfetamine: <1 hour; Dextroamphetamine: 10–12 h
Duration of action	10–14 hours
Excretion	Kidney: ~2% as Lisdexamfetamine and ~42% as Dextroamphetamine
Identifiers
	IUPAC name (2S)-2,6-Diamino-N-[(1S)-1-methyl-2-phenylethyl]hexanamide;
CAS Number	608137-32-2 [IUPHAR];
PubChem CID	11597698;
IUPHAR/BPS	7213;
DrugBank	DB01255 ;
ChemSpider	9772458 ;
UNII	H645GUL8KJ;
KEGG	D08130; as salt: D04747;
ChEMBL	ChEMBL1201222 ;
CompTox Dashboard (EPA)	DTXSID00209652 ;
Chemical and physical data
Formula	C15H25N3O
Molar mass	263.385 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Dextrorotatory enantiomer
Density	Not routinely reported for solid pharmaceutical salts
Melting point	Decomposes before a distinct melting point
Boiling point	Not applicable; decomposes before boiling
Solubility in water	Freely soluble in water
	SMILES O=C(N[C@H](Cc1ccccc1)C)[C@@H](N)CCCCN;
	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 ; Key:VOBHXZCDAVEXEY-JSGCOSHPSA-N ;
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Lisdexamfetamine, sold under the brand names Vyvanse (/'vai.væns/) 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.