Back لسدكسامفيتامين Arabic لیسدکسافیتامین AZB Lisdexamfetamin German Lisdexanfetamina Spanish لیزدگزامفتامین مزیلات Persian Lisdeksamfetamiini Finnish Lisdexamfétamine French ליסדקסאמפטמין HE Lisdexamfetamina Italian リスデキサンフェタミン Japanese

Lisdexamfetamine

Not to be confused with Levoamphetamine.

Lisdexamfetamine
Clinical data
Trade namesVyvanse, Tyvense, Elvanse, 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
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][7]
Duration of action10–12 hours[14][11][12]
ExcretionKidney: ~2%
Identifiers
  • (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)
  • 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 checkY
  • Key:VOBHXZCDAVEXEY-JSGCOSHPSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Lisdexamfetamine, sold under the brand names Vyvanse and Elvanse among others, is a stimulant medication that is used to treat 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 two hours and last for up to 14 hours.[15] In the United Kingdom, it is usually less preferred to methylphenidate for the treatment of children.[16]

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 per the United States Food and Drug Administration.[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.[17][15][18]

Lisdexamfetamine is an inactive prodrug that works after being converted by the body into dextroamphetamine, a central nervous system (CNS) stimulant.[15][19] Chemically, lisdexamfetamine is composed of the amino acid L-lysine, attached to dextroamphetamine.[20]

Lisdexamfetamine was approved for medical use in the United States in 2007, and in the European Union in 2012.[15][21] In 2021, it was the 69th most commonly prescribed medication in the United States, with more than 9 million prescriptions.[22][23] 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.[17][24]

  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. ^ "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.
  4. ^ "Australian Product Information Vyanse® (Lisdexamfetamine dimesilate)" (PDF). Department of Health and Aged Care. Archived (PDF) from the original on 22 January 2023.
  5. ^ 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.
  6. ^ "Vyvanse Product information". Health Canada. 15 December 2021. Retrieved 18 March 2024.
  7. ^ a b "Vyvanse- lisdexamfetamine dimesylate capsule; Vyvanse- lisdexamfetamine dimesylate tablet, chewable". DailyMed. 10 March 2022. Retrieved 19 December 2022.
  8. ^ "List of nationally authorised medicinal products : Active substance(s): lisdexamfetamine : Procedure No. PSUSA/00010289/202002" (PDF). Ema.europa.eu. Retrieved 12 March 2022.
  9. ^ "Public Assessment Report Decentralised Procedure" (PDF). MHRA. p. 14. Archived from the original (PDF) on 26 August 2014. Retrieved 23 August 2014.
  10. ^ Wishart DS, Djombou Feunang Y, Guo AC, Lo EJ, Marcu A, Grant JR, et al. "Amphetamine | DrugBank Online". DrugBank. 5.0.
  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. ^ "Attention deficit hyperactivity disorder: diagnosis and management". NICE. 14 March 2018. Retrieved 21 April 2022.
  17. ^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 348–349. ISBN 978-0-85711-338-2.
  18. ^ "Lisdexamfetamine (Vyvanse) Use During Pregnancy". Drugs.com. Retrieved 16 April 2019.
  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. ^ 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.
  21. ^ "Shire's ADHD amphetamine wins British backing". Reuters. 12 December 2012. Retrieved 14 December 2023.
  22. ^ "The Top 300 of 2021". ClinCalc. Retrieved 14 January 2024.
  23. ^ "Lisdexamfetamine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  24. ^ Drugs of Abuse (PDF). Drug Enforcement Administration • U.S. Department of Justice. 2017. p. 22. Retrieved 16 April 2019.

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