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

• ChemBase编号: 1124
• 分子式: C15H25N3O
• 平均质量: 263.3785
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide
• IUPAC传统名: vyvanse
• 商标名: Vyvanse
• 别名: (2S)-2,6-Diamino-N-[(1S)-1-methyl-2-phenylethyl]hexanamide DiHydrochloride; Lisdexamphetamine Dihydrochloride; NRP104; lisdexamfetamine dimesylate; Lisdexamfetamine

登记号

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

理论计算性质

JChem

• Acid pKa: 15.885676
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -4.57143
• LogD (pH = 7.4): -2.5414438
• Log P: 1.1358308
• 摩尔折射率: 78.3148 cm^3
• 极化性: 31.178019 Å^3
• 极化表面积: 81.14 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.01
• LOG S: -3.48
• 溶解度: 8.77e-02 g/l

分子性质

理化性质

• 溶解度: 792 mg/mL (dimesylate salt); DMSO; Methanol
• 外观: Pale Beige Solid
• 熔点: 100-102°C
• 疏水性(logP): 1.06

安全信息

• 保存条件: Controlled Substance, -20°C Freezer

详细说明

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.

参考文献

• 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)