Accession Number

Also known as Vyvanse, lisdexamfetamine (L-lysine-d-amphetamine) is a prodrug of the psychostimulant d-amphetamine 4. It is paired with the essential amino acid L-lysine. Lisdexamfetamine dimesylate increases attention span and decreases restlessness in children and adults who are overactive/hyperactive, cannot concentrate for long periods, or are easily distracted or impulsive 2.

As a central nervous system stimulant, lisdexamfetamine is utilized as an adjunct therapy in the treatment of attention deficit hyperactivity disorder (ADHD). As a prodrug, lisdexamfetamine was specifically engineered as an abuse-resistant product 10. The mechanism by which this occurs is through delayed release after ingestion (unlike some other psychostimulant drugs, which may be abused). After oral administration and absorption, enzyme hydrolysis after contact with red blood cells metabolize lisdexamfetamine into L- lysine, a naturally occurring essential amino acid and active d-amphetamine, which is responsible for the drug’s pharmacological effects. Gastrointestinal pH does not affect this conversion, and the addition of the L-lysine slows the amount of d-amphetamine available in the circulation and central nervous system 10.

Small Molecule
Approved, Investigational
Average: 263.3785
Monoisotopic: 263.199762437
Chemical Formula
  • Lisdexamfetamine



For the treatment of Attention-deficit/hyperactivity disorder (ADHD) and for moderate to severe binge eating disorder in adults Label, 4.

This drug is not indicated for weight loss. Use of other sympathomimetic drugs for weight loss is associated with serious cardiovascular effects. The safety and effectiveness of this drug for the treatment of obesity have not yet been determined Label.

Associated Conditions
Contraindications & Blackbox Warnings
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Lisdexamfetamine dimesylate is a prodrug of d-amphetamine. Amphetamines are non-catecholamine sympathomimetic amines with CNS stimulating properties Label. This agent works primarily by inducing the release of the neurotransmitters dopamine and norepinephrine from their storage areas in presynaptic nerve terminals 9. Both of these transmitters contribute to alertness, increased concentration, in addition to effort and motivation.

Mechanism of action

Lisdexamfetamine is a prodrug of dextroamphetamine. The active form of this drug blocks the reuptake of norepinephrine and dopamine into the presynaptic neuron and increase the release of these monoamines into the extraneuronal space. The parent drug, lisdexamfetamine, does not bind to the sites for the reuptake of norepinephrine and dopamine in vitro Label. The mechanism of therapeutic action in attention deficit hyperactivity disorder (ADHD) is not fully understood 8, Label. Amphetamines have been recently found to target the trace amine-associated receptor 1 (TAAR1), which was recently discovered. This may explain some of its effects on the extraneuronal space 5, 6,7. Ultimately, the ability of this agent to increase synaptic concentrations of the catecholamine neurotransmitters noradrenaline and dopamine in the prefrontal cortex (PFC), and in the striatum, results in several behavioral changes 9, Label.

UTrace amine-associated receptor 1

After oral administration, lisdexamfetamine is rapidly absorbed from the gastrointestinal tract Label, 8.

Chewable tablet form: After a single dose of 60 mg a chewable tablet in healthy subjects under fasted conditions, the Tmax of lisdexamfetamine and dextroamphetamine was reached at about 1 hour and 4.4 hour post administration, respectively Label.

Capsule form: Following single-dose oral (30 mg, 50 mg, or 70 mg) in patients ages 6 to 12 years with ADHD under fasted conditions, Tmax of lisdexamfetamine and dextroamphetamine was reached at about 1 hour and 3.5 hours post administration, respectively Label.

Volume of distribution

There is no accumulation of d-amphetamine (as measured by AUC) at steady state in healthy adults and no accumulation of lisdexamfetamine dimesylate after once-daily dosing for seven consecutive days Label, 8.

Protein binding
Not Available

THe conversion of Lisdexamfetamine dimesylate (LDX) to the active metabolite d-amphetamine occurs primarily in the blood through enzymatic cleavage after active absorption of LDX from the gastrointestinal lumen 4. Lisdexamfetamine dimesylate is hydrolyzed in the blood to d-amphetamine, which is responsible for the drug’s therapeutic activity, as well as L-lysine. Amphetamine is reported to be oxidized at the 4 position of the benzene ring to form 4-hydroxyamphetamine, or on the side chain α or β carbons to form alpha-hydroxy-amphetamine or norephedrine, respectively. Norephedrine and 4-hydroxy-amphetamine are both active and each is subsequently oxidized to form 4-hydroxy-norephedrine. Alpha-hydroxy-amphetamine undergoes the process of deamination to form phenylacetone, which finally forms benzoic acid and its glucuronide and the glycine conjugate, hippuric acid. Although the enzymes involved in amphetamine metabolism have not been clearly identified, CYP2D6 is known to be involved with the formation of 4-hydroxy-amphetamine from amphetamine 8.

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Route of elimination

After the oral administration of a 70mg dose of radiolabeled lisdexamfetamine dimesylate to six healthy subjects, about 96% of the oral dose radioactivity was recovered in the urine and only 0.3% recovered in the feces Label, 8.


The mean plasma elimination half-life of dextroamphetamine was about 12 hours after oral administration of lisdexamfetamine dimesylate Label.

The plasma elimination half-life of lisdexamfetamine alone averaged less than one hour in studies of lisdexamfetamine dimesylate administered in volunteer subjects Label.


In a study of 47 subjects aged 55 years of age or older, amphetamine clearance was approximately 0.7L/hr/kg for subjects 55-74 years of age and 0.55L/hr/kg for subjects ≥75 years of age. This is slightly reduced compared to younger adults (approximately 1L/hr/kg for subjects 18-45 years of age) 8.

Adverse Effects
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Acute toxicity: Symptoms of acute overdosage with amphetamines include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, panic states, hyperpyrexia, and rhabdomyolysis. Fatigue and depression generally follow the symptoms central nervous system stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension and/or circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Lethal poisoning is usually preceded by convulsions and coma Label. Prescribers should consider that serious cardiovascular (CV) events have been reported with this class of drugs 8.

Long-term effects: Acute administration of high doses of amphetamine (d- or d,l-) has been shown to produce long-term neurotoxic effects, which include irreversible nerve fiber damage, in rodents. The relevance of these findings to humans is currently unknown Label.

Oral LD50 (rat): 7,060 mg/kg MSDS

Oral LD50 (mouse): 3,450 mg/kg MSDS

Use in Pregnancy

This drug is categorized as a Pregnancy Category C: Animal studies have shown risk to the fetus, there are no controlled studies in women, or studies in women and animals are not available Label.

Affected organisms
  • Humans and other mammals
Not Available
Pharmacogenomic Effects/ADRs
Not Available


Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
AbaloparatideThe risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Abaloparatide.
AbataceptThe metabolism of Lisdexamfetamine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Lisdexamfetamine can be decreased when combined with Abiraterone.
AcebutololThe therapeutic efficacy of Acebutolol can be decreased when used in combination with Lisdexamfetamine.
AceclofenacThe risk or severity of hypertension can be increased when Lisdexamfetamine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Lisdexamfetamine is combined with Acemetacin.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Lisdexamfetamine.
AcetazolamideAcetazolamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Lisdexamfetamine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Lisdexamfetamine.
Additional Data Available
  • Extended Description
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  • Severity

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  • Evidence Level
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  • Action

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Food Interactions
  • Avoid antacids. Urinary excretion of lisdexamfetamine is elevated when the urine is more acidic. Antacids like sodium bicarbonate alkalinize the urine; therefore, they may reduce lisdexamfetamine elimination.
  • Limit foods and supplements high in vitamin C. Urinary excretion of lisdexamfetamine is elevated when the urine is more acidic. Vitamin C acidifies the urine and, therefore, may increase lisdexamfetamine elimination.
  • Take with or without food.


Product Ingredients
IngredientUNIICASInChI Key
Lisdexamfetamine dimesylateSJT761GEGS608137-33-3CETWSOHVEGTIBR-FORAGAHYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VyvanseTablet, chewable50 mg/1OralShire LLC2017-01-28Not applicableUS flag
VyvanseCapsule50 mgOralTakeda2009-08-04Not applicableCanada flag
VyvanseCapsule70 mgOralTakeda2017-01-05Not applicableCanada flag
VyvanseTablet, chewable50 mgOralTakeda2019-08-06Not applicableCanada flag
VyvanseCapsule40 mg/1OralShire LLC2007-12-10Not applicableUS flag
VyvanseTablet, chewable20 mg/1OralShire LLC2017-01-28Not applicableUS flag
VyvanseCapsule10 mg/1OralAvera McKennan Hospital2015-03-262017-05-24US flag
VyvanseCapsule40 mgOralTakeda2010-04-14Not applicableCanada flag
VyvanseCapsule10 mg/1OralShire LLC2014-08-30Not applicableUS flag
VyvanseTablet, chewable20 mgOralTakeda2019-08-06Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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ATC Codes
N06BA12 — Lisdexamfetamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Organic compounds
Super Class
Organic acids and derivatives
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Amphetamines and derivatives / Phenylpropanes / N-acyl amines / Secondary carboxylic acid amides / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Alpha-amino acid amide / Amine / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Fatty acyl / Fatty amide / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

CAS number
InChI Key
C[[email protected]@H](CC1=CC=CC=C1)NC(=O)[[email protected]@H](N)CCCCN


Synthesis Reference

Michael J. Bauer, Gary Richard Callen, Judi Christine Humphrey, Todd Jeffrey Johnson, Matthew Wendell Schiesher, "Methods and Compositions for Preparing Lisdexamfetamine and Salts Thereof." U.S. Patent US20120157706, issued June 21, 2012.

General References
  1. Jasinski DR, Krishnan S: Human pharmacology of intravenous lisdexamfetamine dimesylate: abuse liability in adult stimulant abusers. J Psychopharmacol. 2009 Jun;23(4):410-8. doi: 10.1177/0269881108093841. Epub 2008 Jul 17. [PubMed:18635707]
  2. Madaan V: Lisdexamfetamine dimesylate for childhood ADHD. Drugs Today (Barc). 2008 May;44(5):319-24. doi: 10.1358/dot.2008.44.5.1215724. [PubMed:18548134]
  3. 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:17035599]
  4. Goodman DW: Lisdexamfetamine dimesylate (vyvanse), a prodrug stimulant for attention-deficit/hyperactivity disorder. P T. 2010 May;35(5):273-87. [PubMed:20514273]
  5. Miller GM: The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity. J Neurochem. 2011 Jan;116(2):164-76. doi: 10.1111/j.1471-4159.2010.07109.x. [PubMed:21073468]
  6. Liu JF, Li JX: TAAR1 in Addiction: Looking Beyond the Tip of the Iceberg. Front Pharmacol. 2018 Mar 27;9:279. doi: 10.3389/fphar.2018.00279. eCollection 2018. [PubMed:29636691]
  7. Pei Y, Asif-Malik A, Canales JJ: Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications. Front Neurosci. 2016 Apr 5;10:148. doi: 10.3389/fnins.2016.00148. eCollection 2016. [PubMed:27092049]
  8. Vyvanse, Canadian Monograph [File]
  9. EPAR: Lisdexamfetamine dimesylate [File]
  10. WHO Summary: Lisdexamfetamine [File]
Human Metabolome Database
PubChem Compound
PubChem Substance
Therapeutic Targets Database
RxList Drug Page Drug Page
AHFS Codes
  • 28:20.04 — Amphetamines
FDA label
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Clinical Trials

Clinical Trials
4CompletedNot AvailableAttention Deficit Hyperactivity Disorder (ADHD)2
4CompletedBasic ScienceAttention Deficit Hyperactivity Disorder (ADHD)1
4CompletedBasic ScienceAttention Deficit/Hyperactivity Disorder1
4CompletedTreatmentADHD Specifically With Executive Function Impairment1
4CompletedTreatmentAdult Attention Deficit Hyperactivity Disorder (ADHD) With Co-occuring Anxiety and Depressive Disorders1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD)3
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Attention Deficit/Hyperactivity Disorder4
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Attention Deficit/Hyperactivity Disorder / Deficient Emotional Self-Regulation (DESR)1
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Traumatic Brain Injury (TBI)1


Not Available
  • New River Pharmaceuticals Inc.
  • Patheon Inc.
  • Physicians Total Care Inc.
  • Quality Care
  • Shire Inc.
Dosage Forms
CapsuleOral30 mg
CapsuleOral50 mg
CapsuleOral70 mg
Capsule, coatedOral50 mg
Capsule, coatedOral70 mg
Capsule, coatedOral30 mg
CapsuleOral10 mg
CapsuleOral10 mg/1
CapsuleOral20 mg/1
CapsuleOral20 mg
CapsuleOral30 mg/1
CapsuleOral40 mg
CapsuleOral40 mg/1
CapsuleOral50 mg/1
CapsuleOral60 mg
CapsuleOral60 mg/1
CapsuleOral70 mg/1
Tablet, chewableOral10 mg/1
Tablet, chewableOral10 mg
Tablet, chewableOral20 mg/1
Tablet, chewableOral20 mg
Tablet, chewableOral30 mg/1
Tablet, chewableOral30 mg
Tablet, chewableOral40 mg
Tablet, chewableOral40 mg/1
Tablet, chewableOral50 mg
Tablet, chewableOral50 mg/1
Tablet, chewableOral60 mg/1
Tablet, chewableOral60 mg
Unit descriptionCostUnit
Vyvanse 30 mg capsule6.24USD capsule
Vyvanse 50 mg capsule6.02USD capsule
Vyvanse 70 mg capsule5.85USD capsule
Vyvanse 40 mg capsule5.8USD capsule
Vyvanse 20 mg capsule5.26USD capsule
Vyvanse 60 mg capsule5.02USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7659253No2010-02-092023-02-24US flag
US7718619No2010-05-182023-02-24US flag
US7659254No2010-02-092023-02-24US flag
US7671030No2010-03-022023-02-24US flag
US7662788No2010-02-162023-02-24US flag
US7687467No2010-03-302023-02-24US flag
US7678770No2010-03-162023-02-24US flag
US7671031No2010-03-022023-02-24US flag
US7713936No2010-05-112023-02-24US flag
US7674774No2010-03-092023-02-24US flag
US7678771No2010-03-162023-02-24US flag
US7655630No2010-02-022023-02-24US flag
US7687466No2010-03-302023-02-24US flag
US7223735No2007-05-292023-02-24US flag
US7700561No2010-04-202023-02-24US flag
US7662787No2010-02-162023-02-24US flag
US7723305No2010-05-252023-02-24US flag
US7105486No2006-09-122023-02-24US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more


Experimental Properties
water solubility792 mg/mL (dimesylate salt)FDA label
Predicted Properties
Water Solubility0.0877 mg/mLALOGPS
pKa (Strongest Acidic)15.89ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81.14 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.31 m3·mol-1ChemAxon
Polarizability31.28 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Human Intestinal Absorption+0.9858
Blood Brain Barrier+0.9444
Caco-2 permeable+0.664
P-glycoprotein substrateSubstrate0.6919
P-glycoprotein inhibitor INon-inhibitor0.9264
P-glycoprotein inhibitor IINon-inhibitor0.9802
Renal organic cation transporterNon-inhibitor0.8398
CYP450 2C9 substrateNon-substrate0.8303
CYP450 2D6 substrateNon-substrate0.621
CYP450 3A4 substrateNon-substrate0.7228
CYP450 1A2 substrateNon-inhibitor0.7025
CYP450 2C9 inhibitorNon-inhibitor0.9337
CYP450 2D6 inhibitorNon-inhibitor0.858
CYP450 2C19 inhibitorNon-inhibitor0.7568
CYP450 3A4 inhibitorNon-inhibitor0.5499
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8494
Ames testNon AMES toxic0.7156
BiodegradationNot ready biodegradable0.8575
Rat acute toxicity2.0058 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9688
hERG inhibition (predictor II)Non-inhibitor0.9004
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)


Mass Spec (NIST)
Not Available
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available


Pharmacological action
General Function
Trace-amine receptor activity
Specific Function
Receptor for trace amines, including beta-phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amin...
Gene Name
Uniprot ID
Uniprot Name
Trace amine-associated receptor 1
Molecular Weight
39091.34 Da
  1. Miller GM: The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity. J Neurochem. 2011 Jan;116(2):164-76. doi: 10.1111/j.1471-4159.2010.07109.x. [PubMed:21073468]
  2. Liu JF, Li JX: TAAR1 in Addiction: Looking Beyond the Tip of the Iceberg. Front Pharmacol. 2018 Mar 27;9:279. doi: 10.3389/fphar.2018.00279. eCollection 2018. [PubMed:29636691]
  3. Pei Y, Asif-Malik A, Canales JJ: Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications. Front Neurosci. 2016 Apr 5;10:148. doi: 10.3389/fnins.2016.00148. eCollection 2016. [PubMed:27092049]


Pharmacological action
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
Uniprot ID
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
  1. Hutson PH, Pennick M, Secker R: Preclinical pharmacokinetics, pharmacology and toxicology of lisdexamfetamine: a novel d-amphetamine pro-drug. Neuropharmacology. 2014 Dec;87:41-50. doi: 10.1016/j.neuropharm.2014.02.014. Epub 2014 Mar 1. [PubMed:24594478]
  2. Tan-Kam T, Suthisisang C, Pavasuthipaisit C, Limsila P, Puangpetch A, Sukasem C: Importance of pharmacogenetics in the treatment of children with attention deficit hyperactive disorder: a case report. Pharmgenomics Pers Med. 2013;6:3-7. doi: 10.2147/PGPM.S36782. Epub 2013 Jan 11. [PubMed:23526481]
  3. Vyvanse FDA label [File]


Pharmacological action
Curator comments
These data are based on in vitro studies.
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
Uniprot ID
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
  1. Pennick M: Absorption of lisdexamfetamine dimesylate and its enzymatic conversion to d-amphetamine. Neuropsychiatr Dis Treat. 2010 Jun 24;6:317-27. [PubMed:20628632]
  2. Elvanse EPAR [File]

Drug created on May 14, 2007 19:24 / Updated on October 21, 2020 01:55

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