Lisdexamfetamine dimesylateProduct ingredient for Lisdexamfetamine
- Name
- Lisdexamfetamine dimesylate
- Drug Entry
- Lisdexamfetamine
Lisdexamfetamine is a prodrug of dextroamphetamine, a central nervous system stimulant known as d-amphetamine,3 covalently attached to the naturally occurring amino acid L-lysine.1 Lisdexamfetamine is the first chemically formulated prodrug stimulant 3 and was first approved by the FDA in April 2008.1 It was also approved by Health Canada in February 2009.7 Lisdexamfetamine works to treat attention deficit hyperactivity disorder and binge eating disorder 1 by blocking dopamine and norepinephrine reuptake and increasing their levels in the extraneuronal space.6
- Accession Number
- DBSALT002824
- Structure
Structure for Lisdexamfetamine dimesylate (DBSALT002824)
- Synonyms
- Lis-dexamfetamine dimesylate / Lisdexamfetamine mesilate
- External IDs
- NRP 104 / NRP-104 / NRP104 / SPD 489 / SPD489
- UNII
- SJT761GEGS
- CAS Number
- 608137-33-3
- Weight
- Average: 455.59
Monoisotopic: 455.175992763 - Chemical Formula
- C17H33N3O7S2
- InChI Key
- CETWSOHVEGTIBR-FORAGAHYSA-N
- InChI
- InChI=1S/C15H25N3O.2CH4O3S/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16;2*1-5(2,3)4/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19);2*1H3,(H,2,3,4)/t12-,14-;;/m0../s1
- IUPAC Name
- (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide; bis(methanesulfonic acid)
- SMILES
- CS(O)(=O)=O.CS(O)(=O)=O.C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN
- External Links
- ChemSpider
- 9772457
- ChEMBL
- CHEMBL1201178
- PharmGKB
- PA164748975
- Wikipedia
- Lisdexamfetamine
- Predicted Properties
Property Value Source Water Solubility 0.0877 mg/mL ALOGPS logP 1.01 ALOGPS logP 1.14 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 15.89 Chemaxon pKa (Strongest Basic) 10.21 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 81.14 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 78.31 m3·mol-1 Chemaxon Polarizability 31.28 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon