(2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide

• ChemBase ID: 1124
• Molecular Formular: C15H25N3O
• Molecular Mass: 263.3785
• Monoisotopic Mass: 263.19976244
• SMILES: c1ccccc1C[C@@H](NC(=O)[C@H](CCCCN)N)C
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](Cc1ccccc1)C)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
• InChIKey: VOBHXZCDAVEXEY-JSGCOSHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide
• IUPAC Traditional name: vyvanse
• Brand Name: Vyvanse
• Synonyms: (2S)-2,6-Diamino-N-[(1S)-1-methyl-2-phenylethyl]hexanamide DiHydrochloride; Lisdexamphetamine Dihydrochloride; NRP104; lisdexamfetamine dimesylate; Lisdexamfetamine

Database IDs

• CAS Number: 608137-32-2; 914480-48-1
• PubChem SID: 46505358; 160964587
• PubChem CID: 11597698

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.885676
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -4.57143
• LogD (pH = 7.4): -2.5414438
• Log P: 1.1358308
• Molar Refractivity: 78.3148 cm^3
• Polarizability: 31.178019 Å^3
• Polar Surface Area: 81.14 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.01
• LOG S: -3.48
• Solubility (Water): 8.77e-02 g/l

PROPERTIES

Physical Property

• Solubility: 792 mg/mL (dimesylate salt); DMSO; Methanol
• Apperance: Pale Beige Solid
• Melting Point: 100-102°C
• Hydrophobicity(logP): 1.06

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

DrugBank - DB01255

• Drug Groups: approved; investigational
• Description: Lisdexamfetamine (L-lysine-d-amphetamine) is a prodrug of the psychostimulant d-amphetamine coupled with the essential amino acid L-lysine. It was developed so that the amphetamine psychostimulant is released and activated more slowly as the prodrug molecule is hydrolyzed consequently cleaving off the amino acid-during the first pass through the intestines and/or the liver. Amphetamines target the trace amine-associated receptor 1 (TAAR1). Amphetamine is also believed to exert its effects by binding to the monoamine transporters (the dopamine transporter or DAT) and increasing extracellular levels of the biogenic amines dopamine, norepinephrine (noradrenaline) and serotonin.
• Indication: For the treatment of Attention Deficit/Hyperactivity Disorder (ADHD) in pediatric populations aged 6 to 12 years.
• Pharmacology: Lisdexamfetamine is a pro-drug of dextroamphetamine. It works primarily by inducing the release of the neurotransmitters dopamine and norepinephrine from their storage areas in nerve terminals. Both of these transmitters contribute to maintaining alertness, increasing focus, and sustaining thought, effort, and motivation.
• Toxicity: Manifestations of acute overdosage with amphetamines include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, panic states, hyperpyrexia and rhabdomyolysis. Fatigue and depression usually follow the central nervous system stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Fatal poisoning is usually preceded by convulsions and coma.
• Affected Organisms: Humans and other mammals
• Biotransformation: Lisdexamfetamine is converted to dextroamphetamine and L-lysine, which is believed to occur by first-pass intestinal and/or hepatic metabolism. Lisdexamfetamine is not metabolized by cytochrome P450 enzymes.
• Absorption: After oral administration, lisdexamfetamine is rapidly absorbed from the gastrointestinal tract.
• Half Life: The plasma elimination half-life of lisdexamfetamine typically averaged less ; than one hour.
• References: Jasinski DR, Krishnan S: Human pharmacology of intravenous lisdexamfetamine dimesylate: abuse liability in adult stimulant abusers. J Psychopharmacol. 2008 Jul 17. [Pubmed] ; Madaan V: Lisdexamfetamine dimesylate for childhood ADHD. Drugs Today (Barc). 2008 May;44(5):319-24. [Pubmed] ; Krishnan S, Moncrief S: An evaluation of the cytochrome p450 inhibition potential of lisdexamfetamine in human liver microsomes. Drug Metab Dispos. 2007 Jan;35(1):180-4. Epub 2006 Oct 11. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - L468880

Lisdexamfetamine, a new, novel amphetamine product, has been shown to provide efficacy upwards of 12 h in children and adults with a side effect profile similar to those of other longer-acting amphetamine products.Controlled substance.

REFERENCES

• Jasinski DR, Krishnan S: Human pharmacology of intravenous lisdexamfetamine dimesylate: abuse liability in adult stimulant abusers. J Psychopharmacol. 2008 Jul 17. Pubmed
• Krishnan S, Moncrief S: An evaluation of the cytochrome p450 inhibition potential of lisdexamfetamine in human liver microsomes. Drug Metab Dispos. 2007 Jan;35(1):180-4. Epub 2006 Oct 11. Pubmed
• Madaan V: Lisdexamfetamine dimesylate for childhood ADHD. Drugs Today (Barc). 2008 May;44(5):319-24. Pubmed
• Biederman, J., et al.: Clin. Ther., 29, 450 (2007)
• Medori, R., et al.: Biol. Psychiatry., 63, 981 (2007)
• Krishnan, S., et al.: Clin. Drug Investig., 28, 745 (2007)
• Ramos-Quiroga, J., et al.: CNS Drugs, 22, 603 (2007)