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Identification
NameLisdexamfetamine
Accession NumberDB01255
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionLisdexamfetamine (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.
Structure
Thumb
Synonyms
Lisdexamfetamine
lisdexamfetamine dimesylate
NRP104
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VyvanseCapsule50 mgOralShire Pharma Canada Ulc2009-08-04Not applicableCanada
VyvanseCapsule20 mg/1OralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2007-12-10Not applicableUs
VyvanseCapsule30 mg/1OralShire LLC2007-02-23Not applicableUs
VyvanseCapsule10 mgOralShire Pharma Canada Ulc2015-06-26Not applicableCanada
VyvanseCapsule40 mg/1OralPhysicians Total Care, Inc.2009-03-20Not applicableUs
VyvanseCapsule70 mg/1OralShire LLC2007-02-23Not applicableUs
VyvanseCapsule20 mgOralShire Pharma Canada Ulc2010-04-13Not applicableCanada
VyvanseCapsule70 mg/1OralPhysicians Total Care, Inc.2010-03-04Not applicableUs
VyvanseCapsule40 mg/1OralShire LLC2007-12-10Not applicableUs
VyvanseCapsule10 mg/1OralAvera Mc Kennan Hospital2015-03-26Not applicableUs
VyvanseCapsule70 mg/1OralAvera Mc Kennan Hospital2015-09-30Not applicableUs
VyvanseCapsule70 mgOralShire Pharma Canada UlcNot applicableNot applicableCanada
VyvanseCapsule40 mgOralShire Pharma Canada Ulc2010-04-14Not applicableCanada
VyvanseCapsule50 mg/1OralPhysicians Total Care, Inc.2008-07-11Not applicableUs
VyvanseCapsule50 mg/1OralShire LLC2007-02-23Not applicableUs
VyvanseCapsule10 mg/1OralShire LLC2014-08-30Not applicableUs
VyvanseCapsule30 mgOralShire Pharma Canada Ulc2009-08-04Not applicableCanada
VyvanseCapsule60 mgOralShire Pharma Canada Ulc2010-04-14Not applicableCanada
VyvanseCapsule30 mg/1OralPhysicians Total Care, Inc.2008-07-11Not applicableUs
VyvanseCapsule60 mg/1OralShire LLC2007-12-10Not applicableUs
VyvanseCapsule20 mg/1OralShire LLC2007-12-10Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIH645GUL8KJ
CAS number608137-32-2
WeightAverage: 263.3785
Monoisotopic: 263.199762437
Chemical FormulaC15H25N3O
InChI KeyVOBHXZCDAVEXEY-JSGCOSHPSA-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
IUPAC Name
(2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide
SMILES
C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN
Pharmacology
IndicationFor the treatment of Attention Deficit/Hyperactivity Disorder (ADHD) in pediatric populations aged 6 to 12 years.
Structured Indications
PharmacodynamicsLisdexamfetamine 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.
Mechanism of actionLisdexamfetamine is a pro-drug of dextroamphetamine. Amphetamines are thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron and increase the release of these monoamines into the extraneuronal space. Norepinephrine and dopamine contribute to maintaining alertness, increasing focus, and sustaining thought, effort, and motivation. However, the exact therapeutic action in ADHD is not known.
TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-1B adrenergic receptorProteinunknown
antagonist
HumanP35368 details
Sodium-dependent dopamine transporterProteinyes
inhibitor
HumanQ01959 details
Related Articles
AbsorptionAfter oral administration, lisdexamfetamine is rapidly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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.

Route of eliminationNot Available
Half lifeThe plasma elimination half-life of lisdexamfetamine typically averaged less than one hour.
ClearanceNot Available
ToxicityManifestations 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of Lisdexamfetamine.Experimental
AcepromazineAcepromazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Vet Approved
AceprometazineAceprometazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
AcetazolamideAcetazolamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved, Vet Approved
AcetophenazineAcetophenazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
AcrivastineLisdexamfetamine may decrease the sedative activities of Acrivastine.Approved
AlcaftadineLisdexamfetamine may decrease the sedative activities of Alcaftadine.Approved
AlfentanilLisdexamfetamine may increase the analgesic activities of Alfentanil.Approved, Illicit
AlimemazineLisdexamfetamine may decrease the sedative activities of Alimemazine.Approved, Vet Approved
AlphacetylmethadolLisdexamfetamine may increase the analgesic activities of Alphacetylmethadol.Experimental, Illicit
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
Aluminum phosphateAluminum phosphate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
AmineptineAmineptine may increase the stimulatory activities of Lisdexamfetamine.Illicit, Withdrawn
AmisulprideAmisulpride may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
AmitriptylineAmitriptyline may increase the stimulatory activities of Lisdexamfetamine.Approved
Ammonium chlorideThe serum concentration of Lisdexamfetamine can be decreased when it is combined with Ammonium chloride.Approved, Vet Approved
AmperozideAmperozide may decrease the stimulatory activities of Lisdexamfetamine.Experimental
AntazolineLisdexamfetamine may decrease the sedative activities of Antazoline.Approved
AripiprazoleAripiprazole may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
AsenapineAsenapine may decrease the stimulatory activities of Lisdexamfetamine.Approved
AstemizoleLisdexamfetamine may decrease the sedative activities of Astemizole.Approved, Withdrawn
AzaperoneAzaperone may decrease the stimulatory activities of Lisdexamfetamine.Vet Approved
AzatadineLisdexamfetamine may decrease the sedative activities of Azatadine.Approved
AzelastineLisdexamfetamine may decrease the sedative activities of Azelastine.Approved
BenmoxinBenmoxin may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
BenperidolBenperidol may decrease the stimulatory activities of Lisdexamfetamine.Investigational
BezitramideLisdexamfetamine may increase the analgesic activities of Bezitramide.Experimental, Illicit, Withdrawn
BifeprunoxBifeprunox may decrease the stimulatory activities of Lisdexamfetamine.Investigational
Bismuth SubcitrateBismuth Subcitrate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
BrexpiprazoleBrexpiprazole may decrease the stimulatory activities of Lisdexamfetamine.Approved
BromperidolBromperidol may decrease the stimulatory activities of Lisdexamfetamine.Investigational
BrompheniramineLisdexamfetamine may decrease the sedative activities of Brompheniramine.Approved
BuclizineLisdexamfetamine may decrease the sedative activities of Buclizine.Approved
BuprenorphineLisdexamfetamine may increase the analgesic activities of Buprenorphine.Approved, Illicit, Investigational, Vet Approved
Butanoic AcidLisdexamfetamine may decrease the sedative activities of Butanoic Acid.Experimental
ButorphanolLisdexamfetamine may increase the analgesic activities of Butorphanol.Approved, Illicit, Vet Approved
Calcium carbonateCalcium carbonate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
CarbinoxamineLisdexamfetamine may decrease the sedative activities of Carbinoxamine.Approved
CarfentanilLisdexamfetamine may increase the analgesic activities of Carfentanil.Illicit, Vet Approved
CariprazineCariprazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
CetirizineLisdexamfetamine may decrease the sedative activities of Cetirizine.Approved
ChloropyramineLisdexamfetamine may decrease the sedative activities of Chloropyramine.Approved
ChlorphenamineLisdexamfetamine may decrease the sedative activities of Chlorphenamine.Approved
ChlorphenoxamineLisdexamfetamine may decrease the sedative activities of Chlorphenoxamine.Withdrawn
ChlorpromazineChlorpromazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Vet Approved
ChlorprothixeneChlorprothixene may decrease the stimulatory activities of Lisdexamfetamine.Approved, Withdrawn
CimetidineLisdexamfetamine may decrease the sedative activities of Cimetidine.Approved
CinnarizineLisdexamfetamine may decrease the sedative activities of Cinnarizine.Approved
ClemastineLisdexamfetamine may decrease the sedative activities of Clemastine.Approved
ClomipramineClomipramine may increase the stimulatory activities of Lisdexamfetamine.Approved, Vet Approved
ClozapineClozapine may decrease the stimulatory activities of Lisdexamfetamine.Approved
CodeineLisdexamfetamine may increase the analgesic activities of Codeine.Approved, Illicit
CyamemazineCyamemazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
CyclizineLisdexamfetamine may decrease the sedative activities of Cyclizine.Approved
CyclobenzaprineCyclobenzaprine may increase the stimulatory activities of Lisdexamfetamine.Approved
CyproheptadineLisdexamfetamine may decrease the sedative activities of Cyproheptadine.Approved
DapiprazoleDapiprazole may decrease the stimulatory activities of Lisdexamfetamine.Approved
DesipramineDesipramine may increase the stimulatory activities of Lisdexamfetamine.Approved
DesloratadineLisdexamfetamine may decrease the sedative activities of Desloratadine.Approved, Investigational
DexbrompheniramineLisdexamfetamine may decrease the sedative activities of Dexbrompheniramine.Approved
Dexchlorpheniramine maleateLisdexamfetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
DextromoramideLisdexamfetamine may increase the analgesic activities of Dextromoramide.Experimental, Illicit
DextropropoxypheneLisdexamfetamine may increase the analgesic activities of Dextropropoxyphene.Approved, Illicit, Withdrawn
DezocineLisdexamfetamine may increase the analgesic activities of Dezocine.Approved
DiclofenamideDiclofenamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
DihydrocodeineLisdexamfetamine may increase the analgesic activities of Dihydrocodeine.Approved, Illicit
DihydroetorphineLisdexamfetamine may increase the analgesic activities of Dihydroetorphine.Experimental, Illicit
DihydromorphineLisdexamfetamine may increase the analgesic activities of Dihydromorphine.Experimental, Illicit
DimenhydrinateLisdexamfetamine may decrease the sedative activities of Dimenhydrinate.Approved
DimetindeneLisdexamfetamine may decrease the sedative activities of Dimetindene.Approved
DimetotiazineLisdexamfetamine may decrease the sedative activities of Dimetotiazine.Approved
DiphenhydramineLisdexamfetamine may decrease the sedative activities of Diphenhydramine.Approved
DiphenoxylateLisdexamfetamine may increase the analgesic activities of Diphenoxylate.Approved, Illicit
DosulepinDosulepin may increase the stimulatory activities of Lisdexamfetamine.Approved
DoxepinLisdexamfetamine may decrease the sedative activities of Doxepin.Approved
DoxylamineLisdexamfetamine may decrease the sedative activities of Doxylamine.Approved, Vet Approved
DPDPELisdexamfetamine may increase the analgesic activities of DPDPE.Investigational
DroperidolDroperidol may decrease the stimulatory activities of Lisdexamfetamine.Approved, Vet Approved
EbastineLisdexamfetamine may decrease the sedative activities of Ebastine.Investigational
EcopipamEcopipam may decrease the stimulatory activities of Lisdexamfetamine.Investigational
EmedastineLisdexamfetamine may decrease the sedative activities of Emedastine.Approved
EpinastineLisdexamfetamine may decrease the sedative activities of Epinastine.Approved, Investigational
EsmirtazapineLisdexamfetamine may decrease the sedative activities of Esmirtazapine.Investigational
EthopropazineLisdexamfetamine may decrease the sedative activities of Ethopropazine.Approved
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with Lisdexamfetamine.Approved
EthoxzolamideEthoxzolamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Withdrawn
EthylmorphineLisdexamfetamine may increase the analgesic activities of Ethylmorphine.Approved, Illicit
EtorphineLisdexamfetamine may increase the analgesic activities of Etorphine.Illicit, Vet Approved
FamotidineLisdexamfetamine may decrease the sedative activities of Famotidine.Approved
FencamfamineFencamfamine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Illicit, Withdrawn
FentanylLisdexamfetamine may increase the analgesic activities of Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineLisdexamfetamine may decrease the sedative activities of Fexofenadine.Approved
FlunarizineLisdexamfetamine may decrease the sedative activities of Flunarizine.Approved
FlupentixolFlupentixol may decrease the stimulatory activities of Lisdexamfetamine.Approved, Withdrawn
FluphenazineFluphenazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
FluspirileneFluspirilene may decrease the stimulatory activities of Lisdexamfetamine.Approved
FurazolidoneFurazolidone may increase the hypertensive activities of Lisdexamfetamine.Approved, Vet Approved
GuanethidineThe serum concentration of Lisdexamfetamine can be decreased when it is combined with Guanethidine.Approved
HaloperidolHaloperidol may decrease the stimulatory activities of Lisdexamfetamine.Approved
HeroinLisdexamfetamine may increase the analgesic activities of Heroin.Approved, Illicit
HexamethylenetetramineThe serum concentration of Lisdexamfetamine can be decreased when it is combined with Hexamethylenetetramine.Approved, Vet Approved
HydracarbazineHydracarbazine may increase the hypertensive activities of Lisdexamfetamine.Approved
HydrocodoneLisdexamfetamine may increase the analgesic activities of Hydrocodone.Approved, Illicit
HydromorphoneLisdexamfetamine may increase the analgesic activities of Hydromorphone.Approved, Illicit
HydroxyzineLisdexamfetamine may decrease the sedative activities of Hydroxyzine.Approved
IloperidoneIloperidone may decrease the stimulatory activities of Lisdexamfetamine.Approved
ImipramineImipramine may increase the stimulatory activities of Lisdexamfetamine.Approved
Ioflupane I-123Lisdexamfetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
IproclozideIproclozide may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Lisdexamfetamine.Approved
IsothipendylLisdexamfetamine may decrease the sedative activities of Isothipendyl.Approved
Kct 0809Lisdexamfetamine may decrease the sedative activities of Kct 0809.Investigational
KetobemidoneLisdexamfetamine may increase the analgesic activities of Ketobemidone.Approved
KetotifenLisdexamfetamine may decrease the sedative activities of Ketotifen.Approved
L-Glutamic AcidThe serum concentration of Lisdexamfetamine can be decreased when it is combined with L-Glutamic Acid.Nutraceutical
LevocabastineLisdexamfetamine may decrease the sedative activities of Levocabastine.Approved
LevocetirizineLisdexamfetamine may decrease the sedative activities of Levocetirizine.Approved
Levomethadyl AcetateLisdexamfetamine may increase the analgesic activities of Levomethadyl Acetate.Approved
LevorphanolLisdexamfetamine may increase the analgesic activities of Levorphanol.Approved
LithiumLithium may decrease the stimulatory activities of Lisdexamfetamine.Approved
LodoxamideLisdexamfetamine may decrease the sedative activities of Lodoxamide.Approved
LofentanilLisdexamfetamine may increase the analgesic activities of Lofentanil.Illicit
LoratadineLisdexamfetamine may decrease the sedative activities of Loratadine.Approved
LoxapineLoxapine may decrease the stimulatory activities of Lisdexamfetamine.Approved
LurasidoneLurasidone may decrease the stimulatory activities of Lisdexamfetamine.Approved
MagaldrateMagaldrate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Withdrawn
Magnesium carbonateMagnesium carbonate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
Magnesium hydroxideMagnesium hydroxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
Magnesium oxideMagnesium oxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
Magnesium TrisilicateMagnesium Trisilicate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
MebanazineMebanazine may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
MeclizineLisdexamfetamine may decrease the sedative activities of Meclizine.Approved
MelperoneMelperone may decrease the stimulatory activities of Lisdexamfetamine.Approved
MepyramineLisdexamfetamine may decrease the sedative activities of Mepyramine.Approved, Vet Approved
MequitazineLisdexamfetamine may decrease the sedative activities of Mequitazine.Approved
MesoridazineMesoridazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
MethadoneLisdexamfetamine may increase the analgesic activities of Methadone.Approved
Methadyl AcetateLisdexamfetamine may increase the analgesic activities of Methadyl Acetate.Approved, Illicit
MethapyrileneLisdexamfetamine may decrease the sedative activities of Methapyrilene.Withdrawn
MethazolamideMethazolamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved
MethotrimeprazineMethotrimeprazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
Methylene blueMethylene blue may increase the hypertensive activities of Lisdexamfetamine.Investigational
MetiamideLisdexamfetamine may decrease the sedative activities of Metiamide.Experimental
MianserinLisdexamfetamine may decrease the sedative activities of Mianserin.Approved
MinaprineMinaprine may increase the hypertensive activities of Lisdexamfetamine.Approved
MirtazapineLisdexamfetamine may decrease the sedative activities of Mirtazapine.Approved
MizolastineLisdexamfetamine may decrease the sedative activities of Mizolastine.Investigational
MoclobemideMoclobemide may increase the hypertensive activities of Lisdexamfetamine.Approved
MolindoneMolindone may decrease the stimulatory activities of Lisdexamfetamine.Approved
MorphineLisdexamfetamine may increase the analgesic activities of Morphine.Approved, Investigational
NalbuphineLisdexamfetamine may increase the analgesic activities of Nalbuphine.Approved
NialamideNialamide may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
NizatidineLisdexamfetamine may decrease the sedative activities of Nizatidine.Approved
NormethadoneLisdexamfetamine may increase the analgesic activities of Normethadone.Approved, Illicit
NortriptylineNortriptyline may increase the stimulatory activities of Lisdexamfetamine.Approved
OctamoxinOctamoxin may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
OlanzapineOlanzapine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
OlopatadineLisdexamfetamine may decrease the sedative activities of Olopatadine.Approved
OndansetronOndansetron may decrease the stimulatory activities of Lisdexamfetamine.Approved
OpipramolOpipramol may increase the stimulatory activities of Lisdexamfetamine.Investigational
OpiumLisdexamfetamine may increase the analgesic activities of Opium.Approved, Illicit
OsanetantOsanetant may decrease the stimulatory activities of Lisdexamfetamine.Investigational
OxycodoneLisdexamfetamine may increase the analgesic activities of Oxycodone.Approved, Illicit, Investigational
OxymorphoneLisdexamfetamine may increase the analgesic activities of Oxymorphone.Approved, Investigational, Vet Approved
PaliperidonePaliperidone may decrease the stimulatory activities of Lisdexamfetamine.Approved
PargylinePargyline may increase the hypertensive activities of Lisdexamfetamine.Approved
PemirolastLisdexamfetamine may decrease the sedative activities of Pemirolast.Approved
PentazocineLisdexamfetamine may increase the analgesic activities of Pentazocine.Approved, Vet Approved
PerazinePerazine may decrease the stimulatory activities of Lisdexamfetamine.Investigational
PerospironePerospirone may decrease the stimulatory activities of Lisdexamfetamine.Approved
PerphenazinePerphenazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
PethidineLisdexamfetamine may increase the analgesic activities of Pethidine.Approved
PhenelzinePhenelzine may increase the hypertensive activities of Lisdexamfetamine.Approved
PhenindamineLisdexamfetamine may decrease the sedative activities of Phenindamine.Approved
PheniprazinePheniprazine may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
PheniramineLisdexamfetamine may decrease the sedative activities of Pheniramine.Approved
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Lisdexamfetamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Lisdexamfetamine.Approved, Vet Approved
PimozidePimozide may decrease the stimulatory activities of Lisdexamfetamine.Approved
PipamperonePipamperone may decrease the stimulatory activities of Lisdexamfetamine.Approved
PipotiazinePipotiazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
PiritramideLisdexamfetamine may increase the analgesic activities of Piritramide.Investigational
PirlindolePirlindole may increase the hypertensive activities of Lisdexamfetamine.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
ProchlorperazineProchlorperazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Vet Approved
PromazinePromazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Vet Approved
PromethazineLisdexamfetamine may decrease the sedative activities of Promethazine.Approved
PropericiazinePropericiazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
ProthipendylProthipendyl may decrease the stimulatory activities of Lisdexamfetamine.Investigational
ProtriptylineProtriptyline may increase the stimulatory activities of Lisdexamfetamine.Approved
QuetiapineQuetiapine may decrease the stimulatory activities of Lisdexamfetamine.Approved
RacloprideRaclopride may decrease the stimulatory activities of Lisdexamfetamine.Investigational
RanitidineLisdexamfetamine may decrease the sedative activities of Ranitidine.Approved
RasagilineRasagiline may increase the hypertensive activities of Lisdexamfetamine.Approved
RemifentanilLisdexamfetamine may increase the analgesic activities of Remifentanil.Approved
RemoxiprideRemoxipride may decrease the stimulatory activities of Lisdexamfetamine.Approved, Withdrawn
ReserpineReserpine may decrease the stimulatory activities of Lisdexamfetamine.Approved
RisperidoneRisperidone may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
RitanserinRitanserin may decrease the stimulatory activities of Lisdexamfetamine.Investigational
Roxatidine acetateLisdexamfetamine may decrease the sedative activities of Roxatidine acetate.Approved
SafrazineSafrazine may increase the hypertensive activities of Lisdexamfetamine.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of Lisdexamfetamine.Approved, Investigational, Vet Approved
SertindoleSertindole may decrease the stimulatory activities of Lisdexamfetamine.Approved, Withdrawn
Spaglumic AcidLisdexamfetamine may decrease the sedative activities of Spaglumic Acid.Approved
SufentanilLisdexamfetamine may increase the analgesic activities of Sufentanil.Approved, Investigational
SulpirideSulpiride may decrease the stimulatory activities of Lisdexamfetamine.Approved
TapentadolLisdexamfetamine may increase the analgesic activities of Tapentadol.Approved
TerfenadineLisdexamfetamine may decrease the sedative activities of Terfenadine.Withdrawn
TesmilifeneLisdexamfetamine may decrease the sedative activities of Tesmilifene.Investigational
ThioproperazineThioproperazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
ThioridazineThioridazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
ThiothixeneThiothixene may decrease the stimulatory activities of Lisdexamfetamine.Approved
ThonzylamineLisdexamfetamine may decrease the sedative activities of Thonzylamine.Approved
TianeptineTianeptine may increase the stimulatory activities of Lisdexamfetamine.Approved
TiaprideTiapride may decrease the stimulatory activities of Lisdexamfetamine.Investigational
ToloxatoneToloxatone may increase the hypertensive activities of Lisdexamfetamine.Approved
TramadolLisdexamfetamine may increase the analgesic activities of Tramadol.Approved, Investigational
TranilastLisdexamfetamine may decrease the sedative activities of Tranilast.Approved, Investigational
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Lisdexamfetamine.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Lisdexamfetamine.Approved
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of Lisdexamfetamine.Approved
TriflupromazineTriflupromazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Vet Approved
TrimipramineTrimipramine may increase the stimulatory activities of Lisdexamfetamine.Approved
TripelennamineLisdexamfetamine may decrease the sedative activities of Tripelennamine.Approved, Vet Approved
TriprolidineLisdexamfetamine may decrease the sedative activities of Triprolidine.Approved
Vitamin CThe serum concentration of Lisdexamfetamine can be decreased when it is combined with Vitamin C.Approved, Nutraceutical
ZiprasidoneZiprasidone may decrease the stimulatory activities of Lisdexamfetamine.Approved
ZotepineZotepine may decrease the stimulatory activities of Lisdexamfetamine.Approved
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
Food InteractionsNot Available
References
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.

US20120157706
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 ]
External Links
ATC CodesN06BA12
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
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
CarcinogenicityNon-carcinogens0.854
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral10 mg
CapsuleOral10 mg/1
CapsuleOral20 mg/1
CapsuleOral20 mg
CapsuleOral30 mg/1
CapsuleOral30 mg
CapsuleOral40 mg
CapsuleOral40 mg/1
CapsuleOral50 mg
CapsuleOral50 mg/1
CapsuleOral60 mg
CapsuleOral60 mg/1
CapsuleOral70 mg
CapsuleOral70 mg/1
Prices
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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7105486 No2003-02-242023-02-24Us
US7223735 No2003-02-242023-02-24Us
US7655630 No2003-02-242023-02-24Us
US7659253 No2003-02-242023-02-24Us
US7659254 No2003-02-242023-02-24Us
US7662787 No2003-02-242023-02-24Us
US7662788 No2003-02-242023-02-24Us
US7671030 No2003-02-242023-02-24Us
US7671031 No2003-02-242023-02-24Us
US7674774 No2003-02-242023-02-24Us
US7678770 No2003-02-242023-02-24Us
US7678771 No2003-02-242023-02-24Us
US7687466 No2003-02-242023-02-24Us
US7687467 No2003-02-242023-02-24Us
US7700561 No2003-02-242023-02-24Us
US7713936 No2003-02-242023-02-24Us
US7718619 No2003-02-242023-02-24Us
US7723305 No2003-02-242023-02-24Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility792 mg/mL (dimesylate salt)Not Available
logP1.06Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0877 mg/mLALOGPS
logP1.01ALOGPS
logP1.14ChemAxon
logS-3.5ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Amphetamine or derivatives
  • Phenylpropane
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 Da
References
  1. Hamidovic A, Dlugos A, Palmer AA, de Wit H: Polymorphisms in dopamine transporter (SLC6A3) are associated with stimulant effects of D-amphetamine: an exploratory pharmacogenetic study using healthy volunteers. Behav Genet. 2010 Mar;40(2):255-61. doi: 10.1007/s10519-009-9331-7. Epub 2010 Jan 21. [PubMed:20091113 ]
Comments
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Drug created on May 14, 2007 19:24 / Updated on December 06, 2016 02:40