Lisdexamfetamine

Not to be confused with Levoamphetamine.

Lisdexamfetamine
Clinical data
Trade namesVyvanse, Elvanse, Tyvense, others
Other namesL-Lysine-d-amphetamine; (2S)-2,6-Diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide
N-[(2S)-1-Phenyl-2-propanyl]-L-lysinamide
AHFS/Drugs.comMonograph
MedlinePlusa607047
License data
Pregnancy
category
  • AU: B3
Dependence
liability		Moderate[1][2]
Addiction
liability		Moderate[1][2]
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S8 (Controlled drug)[3]
  • BR: Class A3 (Psychoactive drugs)[4]
  • CA: Schedule G (CDSA I) [5]
  • DE: Anlage III (Special prescription form required)
  • NZ: Class B
  • UK: Class B
  • US: Schedule II[6]
  • EU: Rx-only[7]
  • SE: Förteckning II[8]
Pharmacokinetic data
BioavailabilityOral: 96.4%[9]
Protein binding20% (as dextroamphetamine)[10]
MetabolismHydrolysis by enzymes in red blood cells initially, subsequent metabolism follows
MetabolitesDextroamphetamine (and its metabolites) and L-lysine
Onset of actionOral: <2 hours[11][12]
Elimination half-lifeLisdexamfetamine: <1 hour[13]
Dextroamphetamine: 10–12 h[13][6]
Duration of action10–14 hours[14][11][12]
ExcretionKidney: ~2%
Identifiers
IUPAC name
  • (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)
Chemical and physical data
FormulaC15H25N3O
Molar mass263.385 g·mol−1
3D model (JSmol)
ChiralityDextrorotatory enantiomer
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?)  (verify)

Lisdexamfetamine, sold under the brand names Vyvanse and Elvanse among others, is a stimulant medication that is used as a treatment for attention deficit hyperactivity disorder (ADHD) in children and adults and for moderate-to-severe binge eating disorder in adults.[15] Lisdexamfetamine is taken by mouth. Its effects generally begin within 90 minutes and last for up to 14 hours.[15]

Common side effects of lisdexamfetamine include loss of appetite, anxiety, diarrhea, trouble sleeping, irritability, and nausea.[15] Rare but serious side effects include mania, sudden cardiac death in those with underlying heart problems, and psychosis.[15] It has a high potential for substance abuse.[6][15] Serotonin syndrome may occur if used with certain other medications.[15] Its use during pregnancy may result in harm to the baby and use during breastfeeding is not recommended by the manufacturer.[16][15][17]

Lisdexamfetamine is an inactive prodrug that is formed by the condensation of L-lysine, a naturally-occurring amino acid, and dextroamphetamine.[18] In the body, metabolic action reverses this process to release the active agent, the central nervous system (CNS) stimulant dextroamphetamine.[15][19]

Lisdexamfetamine was approved for medical use in the United States in 2007 and in the European Union in 2012.[15][20] In 2022, it was the 69th most commonly prescribed medication in the United States, with more than 9 million prescriptions.[21][22] 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.[16][23]

  1. ^ a b "Adderall vs Vyvanse - What's the difference between them?". Drugs.com. Retrieved 12 March 2022.
  2. ^ 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.
  3. ^ "Australian Product Information Vyanse® (Lisdexamfetamine dimesilate)" (PDF). Department of Health and Aged Care. Archived (PDF) from the original on 22 January 2023.
  4. ^ 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.
  5. ^ "Vyvanse Product information". Health Canada. 15 December 2021. Retrieved 18 March 2024.
  6. ^ a b c "Vyvanse- lisdexamfetamine dimesylate capsule; Vyvanse- lisdexamfetamine dimesylate tablet, chewable". DailyMed. 10 March 2022. Retrieved 19 December 2022.
  7. ^ "List of nationally authorised medicinal products : Active substance(s): lisdexamfetamine : Procedure No. PSUSA/00010289/202002" (PDF). Ema.europa.eu. Retrieved 12 March 2022.
  8. ^ "Lisdexamfetamindimesilat". Retrieved 23 January 2025.
  9. ^ "Public Assessment Report Decentralised Procedure" (PDF). MHRA. p. 14. Archived from the original (PDF) on 26 August 2014. Retrieved 23 August 2014.
  10. ^ Knox C, Wilson M, Klinger CM, Franklin M, Oler E, Wilson A, et al. "Amphetamine | DrugBank Online". DrugBank. 6.0.
  11. ^ 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]
  12. ^ 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
  13. ^ a b Cite error: The named reference pmid27021968 was invoked but never defined (see the help page).
  14. ^ 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.
  15. ^ 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.
  16. ^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 348–349. ISBN 978-0-85711-338-2.
  17. ^ "Lisdexamfetamine (Vyvanse) Use During Pregnancy". Drugs.com. Retrieved 16 April 2019.
  18. ^ 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.
  19. ^ 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.
  20. ^ "Shire's ADHD amphetamine wins British backing". Reuters. 12 December 2012. Retrieved 14 December 2023.
  21. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  22. ^ "Lisdexamfetamine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  23. ^ Drugs of Abuse (PDF). Drug Enforcement Administration • U.S. Department of Justice. 2017. p. 22. Retrieved 16 April 2019.
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