Lisdexamfetamine dimesylate

Lisdexamfetamine
Clinical data


Trade names	Tyvense, Elvanse, Venvanse, Vyvanse
AHFS/Drugs.com	Monograph
MedlinePlus	a607047
License data	US FDA: Lisdexamfetamine
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Dependence liability	Physical: none Psychological: moderate
Addiction liability	Moderate
Routes of administration	Oral (capsules)
ATC code	N06BA12 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Prescription only) UK: Class B US: Schedule II In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	96.4%
Metabolism	Hydrolysis by enzymes in red blood cells initially. Subsequent metabolism follows Amphetamine#Pharmacokinetics.
Onset of action	2 hours
Biological half-life	≤1 hour (prodrug molecule) 9–11 hours (dextroamphetamine)
Duration of action	12 hours
Excretion	Renal: ~2%
Identifiers
IUPAC name (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide
Synonyms	Vyvanse
CAS Number	608137-32-2^Y[IUPHAR]
PubChem CID	11597698
IUPHAR/BPS	7213
DrugBank	DB01255^Y
ChemSpider	9772458^Y
UNII	H645GUL8KJ
ChEMBL	CHEMBL1201222^Y
Chemical and physical data
Formula	C₁₅H₂₅N₃O
Molar mass	263.378 g/mol
3D model (Jmol)	Interactive image
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^Y Key:VOBHXZCDAVEXEY-JSGCOSHPSA-N^Y
^NY (what is this?)

Lisdexamfetamine (contracted from L-lysine-dextroamphetamine) is a prodrug of the central nervous system (CNS) stimulant dextroamphetamine, a phenethylamine of the amphetamine class that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and binge eating disorder. Its chemical structure consists of dextroamphetamine coupled with the essential amino acid L-lysine. Lisdexamfetamine itself is inactive prior to its absorption and the subsequent rate-limited enzymatic cleavage of the molecule's L-lysine portion, which produces the active metabolite (dextroamphetamine).

Lisdexamfetamine can be prescribed for the treatment of attention deficit hyperactivity disorder (ADHD) in adults and children six and older, as well as for moderate to severe binge eating disorder in adults. The safety and the efficacy of lisdexamfetamine dimesylate in children with ADHD three to five years old have not been established.

Lisdexamfetamine is a Class B/Schedule II substance in the United Kingdom and a Schedule II controlled substance in the United States (DEA number 1205) and the aggregate production quota for 2016 in the United States is 29,750 kilograms of anhydrous acid or base. Lisdexamfetamine is currently in Phase III trials in Japan for ADHD.

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