Central nervous system stimulant prodrug
Lisdexamfetamine Trade names Vyvanse, Tyvense, Elvanse, others Other names L -Lysine-d-amphetamine; (2S )-2,6-Diamino-N -[(2S )-1-phenylpropan-2-yl]hexanamideN -[(2S )-1-Phenyl-2-propanyl]-L -lysinamideAHFS /Drugs.com Monograph MedlinePlus a607047 License data
Pregnancy category Dependence liability Moderate[ 1] [ 2] Addiction liability Moderate[ 1] [ 2] Routes of administration By mouth ATC code Legal status
Bioavailability Oral : 96.4%[ 9] Protein binding 20% (as dextroamphetamine )[ 10] Metabolism Hydrolysis by enzymes in red blood cells initially, subsequent metabolism followsMetabolites Dextroamphetamine (and its metabolites) and L -lysineOnset of action Oral : <2 hours[ 11] [ 12] Elimination half-life Lisdexamfetamine: <1 hour[ 13] Dextroamphetamine: 10–12 h[ 13] [ 7] Duration of action 10–14 hours[ 14] [ 11] [ 12] Excretion Kidney : ~2%
(2S )-2,6-Diamino-N -[(1S )-1-methyl-2-phenylethyl]hexanamide
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEMBL CompTox Dashboard (EPA ) Formula C 15 H 25 N 3 O Molar mass 263.385 g·mol−1 3D model (JSmol ) Chirality Dextrorotatory enantiomer
O=C(N[C@H](Cc1ccccc1)C)[C@@H](N)CCCCN
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
N Y (what is this?) (verify)
Lisdexamfetamine , sold under the brand names Vyvanse and Elvanse among others, is a stimulant medication that is used medically to treat attention deficit hyperactivity disorder (ADHD) in children and adults, moderate-to-severe binge eating disorder in adults, and cognitive disengagement syndrome (CDS) in adults.[ 15] [ 16] [ 17] [ 18] Lisdexamfetamine is taken by mouth . Its effects generally begin within two hours and last for up to 14 hours.[ 18]
Common side effects of lisdexamfetamine include loss of appetite , anxiety , diarrhea , trouble sleeping , irritability , and nausea .[ 18] Rare but serious side effects include mania , sudden cardiac death in those with underlying heart problems , and psychosis .[ 18] It has a high potential for substance abuse .[ 7] [ 18] Serotonin syndrome may occur if used with certain other medications.[ 18] Its use during pregnancy may result in harm to the baby and use during breastfeeding is not recommended by the manufacturer.[ 19] [ 18] [ 20]
Lisdexamfetamine is an inactive prodrug that works after being converted by the body into dextroamphetamine , a central nervous system (CNS) stimulant .[ 18] [ 21] Chemically, lisdexamfetamine is composed of the amino acid L -lysine , attached to dextroamphetamine.[ 22]
Lisdexamfetamine was approved for medical use in the United States in 2007, and in the European Union in 2012.[ 18] [ 23] In 2021, it was the 69th most commonly prescribed medication in the United States, with more than 9 million prescriptions.[ 24] [ 25] 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.[ 19] [ 26]
^ a b "Adderall vs Vyvanse - What's the difference between them?" . Drugs.com . Retrieved 12 March 2022 .
^ a b Goodman DW (May 2010). "Lisdexamfetamine dimesylate (vyvanse), a prodrug stimulant for attention-deficit/hyperactivity disorder" . P & T . 35 (5): 273–287. PMC 2873712 . PMID 20514273 .
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)" . nctr-crs.fda.gov . FDA . Retrieved 22 October 2023 .
^ "Australian Product Information Vyanse® (Lisdexamfetamine dimesilate)" (PDF) . Department of Health and Aged Care . Archived (PDF) from the original on 22 January 2023.
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 3 August 2023 .
^ "Vyvanse Product information" . Health Canada . 15 December 2021. Retrieved 18 March 2024 .
^ a b c "Vyvanse- lisdexamfetamine dimesylate capsule; Vyvanse- lisdexamfetamine dimesylate tablet, chewable" . DailyMed . 10 March 2022. Retrieved 19 December 2022 .
^ "List of nationally authorised medicinal products : Active substance(s): lisdexamfetamine : Procedure No. PSUSA/00010289/202002" (PDF) . Ema.europa.eu . Retrieved 12 March 2022 .
^ "Public Assessment Report Decentralised Procedure" (PDF) . MHRA. p. 14. Archived from the original (PDF) on 26 August 2014. Retrieved 23 August 2014 .
^ Wishart DS , Djombou Feunang Y, Guo AC, Lo EJ, Marcu A, Grant JR, et al. "Amphetamine | DrugBank Online" . DrugBank . 5.0.
^ a b Millichap JG (2010). "Chapter 9: Medications for ADHD". In Millichap JG (ed.). Attention Deficit Hyperactivity Disorder Handbook: A Physician's Guide to ADHD (2nd ed.). New York, USA: Springer. p. 112. ISBN 978-1-4419-1396-8 . Table 9.2 Dextroamphetamine formulations of stimulant medication Dexedrine [Peak:2–3 h] [Duration:5–6 h] ... Adderall [Peak:2–3 h] [Duration:5–7 h] Dexedrine spansules [Peak:7–8 h] [Duration:12 h] ... Adderall XR [Peak:7–8 h] [Duration:12 h] Vyvanse [Peak:3–4 h] [Duration:12 h]
^ a b Brams M, Mao AR, Doyle RL (September 2008). "Onset of efficacy of long-acting psychostimulants in pediatric attention-deficit/hyperactivity disorder". Postgraduate Medicine . 120 (3): 69–88. doi :10.3810/pgm.2008.09.1909 . PMID 18824827 . S2CID 31791162 . Onset of efficacy was earliest for d-MPH-ER at 0.5 hours, followed by d, l-MPH-LA at 1 to 2 hours, MCD at 1.5 hours, d, l-MPH-OR at 1 to 2 hours, MAS-XR at 1.5 to 2 hours, MTS at 2 hours, and LDX at approximately 2 hours. ... MAS-XR, and LDX have a long duration of action at 12 hours postdose
^ a b Cite error: The named reference pmid27021968
was invoked but never defined (see the help page ).
^ Stahl SM (March 2017). "Lisdexamfetamine". Prescriber's Guide: Stahl's Essential Psychopharmacology (6th ed.). Cambridge, United Kingdom: Cambridge University Press. pp. 379–384. ISBN 978-1-108-22874-9 .
^ Becker SP, Willcutt EG, Leopold DR, Fredrick JW, Smith ZR, Jacobson LA, et al. (June 2023). "Report of a Work Group on Sluggish Cognitive Tempo: Key Research Directions and a Consensus Change in Terminology to Cognitive Disengagement Syndrome" . Journal of the American Academy of Child and Adolescent Psychiatry . 62 (6): 629–645. doi :10.1016/j.jaac.2022.07.821 . PMC 9943858 . PMID 36007816 . {{cite journal }}
: CS1 maint: overridden setting (link )
^ Adler LA, Leon TL, Sardoff TM, Krone B, Faraone SV, Silverstein MJ, et al. (June 2021). "A Placebo-Controlled Trial of Lisdexamfetamine in the Treatment of Comorbid Sluggish Cognitive Tempo and Adult ADHD". The Journal of Clinical Psychiatry . 82 (4): 34965. doi :10.4088/JCP.20m13687 . PMID 34232582 .
^ Wiggs KK, Froehlich TE, Becker SP (April 2023). "Pharmacologic Management of Cognitive Disengagement Syndrome (CDS) and Implications for Attention-Deficit/Hyperactivity Disorder (ADHD) Treatment: Emerging Treatments and Recommendations for Future Research". CNS Drugs . 37 (4): 293–304. doi :10.1007/s40263-023-00999-5 . PMID 37061629 .
^ a b c d e f g h i "Lisdexamfetamine Dimesylate Monograph for Professionals" . Drugs.com . American Society of Health-System Pharmacists. Retrieved 15 April 2019 .
^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 348–349. ISBN 978-0-85711-338-2 .
^ "Lisdexamfetamine (Vyvanse) Use During Pregnancy" . Drugs.com . Retrieved 16 April 2019 .
^ Heal DJ, Smith SL, Gosden J, Nutt DJ (June 2013). "Amphetamine, past and present--a pharmacological and clinical perspective" . Journal of Psychopharmacology . 27 (6): 479–496. doi :10.1177/0269881113482532 . PMC 3666194 . PMID 23539642 .
^ Blick SK, Keating GM (2007). "Lisdexamfetamine". Paediatric Drugs . 9 (2): 129–135, discussion 136–138. doi :10.2165/00148581-200709020-00007 . PMID 17407369 . S2CID 260863254 .
^ "Shire's ADHD amphetamine wins British backing" . Reuters . 12 December 2012. Retrieved 14 December 2023 .
^ "The Top 300 of 2021" . ClinCalc . Retrieved 14 January 2024 .
^ "Lisdexamfetamine - Drug Usage Statistics" . ClinCalc . Retrieved 14 January 2024 .
^ Drugs of Abuse (PDF) . Drug Enforcement Administration • U.S. Department of Justice. 2017. p. 22. Retrieved 16 April 2019 .