Lisdexamfetamine - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (2)

Targets (2)Biointeractions (2)

Identification

Name

Lisdexamfetamine

Accession Number

DB01255

Type

Small Molecule

Groups

Approved, Investigational

Description

Lisdexamfetamine (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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Lisdexamfetamine

lisdexamfetamine dimesylate

NRP104

External IDs

Not Available

Product Ingredients

Not Available

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Vyvanse	Capsule	30 mg	Oral	Shire Pharma Canada Ulc	2009-08-04	Not applicable	Canada
Vyvanse	Capsule	60 mg	Oral	Shire Pharma Canada Ulc	2010-04-14	Not applicable	Canada
Vyvanse	Capsule	20 mg/1	Oral	Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc	2007-12-10	Not applicable	US
Vyvanse	Capsule	20 mg/1	Oral	Shire	2007-12-10	Not applicable	US
Vyvanse	Capsule	60 mg/1	Oral	Shire	2007-12-10	Not applicable	US
Vyvanse	Capsule	50 mg/1	Oral	Shire	2007-02-23	Not applicable	US
Vyvanse	Tablet, chewable	20 mg/1	Oral	Shire	2017-01-28	Not applicable	US
Vyvanse	Capsule	40 mg	Oral	Shire Pharma Canada Ulc	2010-04-14	Not applicable	Canada
Vyvanse	Capsule	30 mg/1	Oral	Physicians Total Care, Inc.	2008-07-11	Not applicable	US
Vyvanse	Capsule	10 mg/1	Oral	Avera Mc Kennan Hospital	2015-03-26	Not applicable	US
Vyvanse	Tablet, chewable	50 mg/1	Oral	Shire	2017-01-28	Not applicable	US
Vyvanse	Capsule	50 mg	Oral	Shire Pharma Canada Ulc	2009-08-04	Not applicable	Canada
Vyvanse	Capsule	10 mg	Oral	Shire Pharma Canada Ulc	2015-06-26	Not applicable	Canada
Vyvanse	Capsule	70 mg/1	Oral	Physicians Total Care, Inc.	2010-03-04	Not applicable	US
Vyvanse	Capsule	30 mg/1	Oral	Shire	2007-02-23	Not applicable	US
Vyvanse	Capsule	70 mg/1	Oral	Shire	2007-02-23	Not applicable	US
Vyvanse	Capsule	40 mg/1	Oral	Physicians Total Care, Inc.	2009-03-20	Not applicable	US
Vyvanse	Tablet, chewable	30 mg/1	Oral	Shire	2017-01-28	Not applicable	US
Vyvanse	Tablet, chewable	60 mg/1	Oral	Shire	2017-01-28	Not applicable	US
Vyvanse	Capsule	10 mg/1	Oral	Shire	2014-08-30	Not applicable	US
Vyvanse	Capsule	40 mg/1	Oral	Shire	2007-12-10	Not applicable	US
Vyvanse	Tablet, chewable	10 mg/1	Oral	Shire	2017-01-28	Not applicable	US
Vyvanse	Capsule	20 mg	Oral	Shire Pharma Canada Ulc	2010-04-13	Not applicable	Canada
Vyvanse	Capsule	70 mg	Oral	Shire Pharma Canada Ulc	2017-01-05	Not applicable	Canada
Vyvanse	Capsule	50 mg/1	Oral	Physicians Total Care, Inc.	2008-07-11	Not applicable	US
Vyvanse	Capsule	70 mg/1	Oral	Avera Mc Kennan Hospital	2015-09-30	Not applicable	US
Vyvanse	Tablet, chewable	40 mg/1	Oral	Shire	2017-01-28	Not applicable	US

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

Categories

UNII

H645GUL8KJ

CAS number

608137-32-2

Weight

Average: 263.3785
Monoisotopic: 263.199762437

Chemical Formula

C₁₅H₂₅N₃O

InChI Key

VOBHXZCDAVEXEY-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

Indication

For the treatment of Attention Deficit/Hyperactivity Disorder (ADHD) in pediatric populations aged 6 to 12 years.

Structured Indications

Pharmacodynamics

Lisdexamfetamine 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 action

Lisdexamfetamine 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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Alpha-1B adrenergic receptor	Protein	unknown	antagonist	Human	P35368	details
Sodium-dependent dopamine transporter	Protein	yes	inhibitor	Human	Q01959	details

Absorption

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

Volume of distribution

Not Available

Protein binding

Not 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 elimination

Not Available

Half life

The plasma elimination half-life of lisdexamfetamine typically averaged less than one hour.

Clearance

Not Available

Toxicity

Manifestations 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

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of Lisdexamfetamine.	Experimental
Acepromazine	Acepromazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Vet Approved
Aceprometazine	Aceprometazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Acetazolamide	Acetazolamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved, Vet Approved
Acetophenazine	Acetophenazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Acrivastine	Lisdexamfetamine may decrease the sedative activities of Acrivastine.	Approved
Alcaftadine	Lisdexamfetamine may decrease the sedative activities of Alcaftadine.	Approved
Alfentanil	Lisdexamfetamine may increase the analgesic activities of Alfentanil.	Approved, Illicit
Alimemazine	Lisdexamfetamine may decrease the sedative activities of Alimemazine.	Approved, Vet Approved
Alphacetylmethadol	Lisdexamfetamine may increase the analgesic activities of Alphacetylmethadol.	Experimental, Illicit
Aluminum hydroxide	Aluminum hydroxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Amineptine	Amineptine may increase the stimulatory activities of Lisdexamfetamine.	Illicit, Withdrawn
Amisulpride	Amisulpride may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Investigational
Amitriptyline	Amitriptyline may increase the stimulatory activities of Lisdexamfetamine.	Approved
Ammonium chloride	The serum concentration of Lisdexamfetamine can be decreased when it is combined with Ammonium chloride.	Approved, Vet Approved
Amperozide	Amperozide may decrease the stimulatory activities of Lisdexamfetamine.	Experimental
Antazoline	Lisdexamfetamine may decrease the sedative activities of Antazoline.	Approved
Aripiprazole	Aripiprazole may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Investigational
Asenapine	Asenapine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Astemizole	Lisdexamfetamine may decrease the sedative activities of Astemizole.	Approved, Withdrawn
Azatadine	Lisdexamfetamine may decrease the sedative activities of Azatadine.	Approved
Azelastine	Lisdexamfetamine may decrease the sedative activities of Azelastine.	Approved
Benmoxin	Benmoxin may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Benperidol	Benperidol may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Bezitramide	Lisdexamfetamine may increase the analgesic activities of Bezitramide.	Experimental, Illicit, Withdrawn
Bifeprunox	Bifeprunox may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Bismuth Subcitrate	Bismuth Subcitrate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Brexpiprazole	Brexpiprazole may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Bromperidol	Bromperidol may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Brompheniramine	Lisdexamfetamine may decrease the sedative activities of Brompheniramine.	Approved
Buclizine	Lisdexamfetamine may decrease the sedative activities of Buclizine.	Approved
Buprenorphine	Lisdexamfetamine may increase the analgesic activities of Buprenorphine.	Approved, Illicit, Investigational, Vet Approved
Butorphanol	Lisdexamfetamine may increase the analgesic activities of Butorphanol.	Approved, Illicit, Vet Approved
Butyric Acid	Lisdexamfetamine may decrease the sedative activities of Butanoic Acid.	Experimental
Calcium Carbonate	Calcium carbonate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Carbinoxamine	Lisdexamfetamine may decrease the sedative activities of Carbinoxamine.	Approved
Carfentanil	Lisdexamfetamine may increase the analgesic activities of Carfentanil.	Illicit, Vet Approved
Cariprazine	Cariprazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Caroxazone	Caroxazone may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Cetirizine	Lisdexamfetamine may decrease the sedative activities of Cetirizine.	Approved
Chloropyramine	Lisdexamfetamine may decrease the sedative activities of Chloropyramine.	Approved
Chlorphenamine	Lisdexamfetamine may decrease the sedative activities of Chlorphenamine.	Approved
Chlorphenoxamine	Lisdexamfetamine may decrease the sedative activities of Chlorphenoxamine.	Withdrawn
Chlorpromazine	Chlorpromazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Vet Approved
Chlorprothixene	Chlorprothixene may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Withdrawn
Cimetidine	Lisdexamfetamine may decrease the sedative activities of Cimetidine.	Approved
Cinnarizine	Lisdexamfetamine may decrease the sedative activities of Cinnarizine.	Approved
Clemastine	Lisdexamfetamine may decrease the sedative activities of Clemastine.	Approved
Clomipramine	Clomipramine may increase the stimulatory activities of Lisdexamfetamine.	Approved, Vet Approved
Clozapine	Clozapine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Codeine	Lisdexamfetamine may increase the analgesic activities of Codeine.	Approved, Illicit
Cyamemazine	Cyamemazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Cyclizine	Lisdexamfetamine may decrease the sedative activities of Cyclizine.	Approved
Cyclobenzaprine	Cyclobenzaprine may increase the stimulatory activities of Lisdexamfetamine.	Approved
Cyproheptadine	Lisdexamfetamine may decrease the sedative activities of Cyproheptadine.	Approved
Dapiprazole	Dapiprazole may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Desipramine	Desipramine may increase the stimulatory activities of Lisdexamfetamine.	Approved
Desloratadine	Lisdexamfetamine may decrease the sedative activities of Desloratadine.	Approved, Investigational
Dexbrompheniramine	Lisdexamfetamine may decrease the sedative activities of Dexbrompheniramine.	Approved
Dexchlorpheniramine maleate	Lisdexamfetamine may decrease the sedative activities of Dexchlorpheniramine maleate.	Approved
Dextromoramide	Lisdexamfetamine may increase the analgesic activities of Dextromoramide.	Experimental, Illicit
Dextropropoxyphene	Lisdexamfetamine may increase the analgesic activities of Dextropropoxyphene.	Approved, Illicit, Withdrawn
Dezocine	Lisdexamfetamine may increase the analgesic activities of Dezocine.	Approved
Diclofenamide	Diclofenamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Dihydrocodeine	Lisdexamfetamine may increase the analgesic activities of Dihydrocodeine.	Approved, Illicit
Dihydroetorphine	Lisdexamfetamine may increase the analgesic activities of Dihydroetorphine.	Experimental, Illicit
Dihydromorphine	Lisdexamfetamine may increase the analgesic activities of Dihydromorphine.	Experimental, Illicit
Dimenhydrinate	Lisdexamfetamine may decrease the sedative activities of Dimenhydrinate.	Approved
Dimetindene	Lisdexamfetamine may decrease the sedative activities of Dimetindene.	Approved
Dimetotiazine	Lisdexamfetamine may decrease the sedative activities of Dimetotiazine.	Approved
Diphenhydramine	Lisdexamfetamine may decrease the sedative activities of Diphenhydramine.	Approved
Diphenoxylate	Lisdexamfetamine may increase the analgesic activities of Diphenoxylate.	Approved, Illicit
Dosulepin	Dosulepin may increase the stimulatory activities of Lisdexamfetamine.	Approved
Doxepin	Lisdexamfetamine may decrease the sedative activities of Doxepin.	Approved
Doxylamine	Lisdexamfetamine may decrease the sedative activities of Doxylamine.	Approved, Vet Approved
Droperidol	Droperidol may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Vet Approved
Ebastine	Lisdexamfetamine may decrease the sedative activities of Ebastine.	Investigational
Ecopipam	Ecopipam may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Emedastine	Lisdexamfetamine may decrease the sedative activities of Emedastine.	Approved
Epinastine	Lisdexamfetamine may decrease the sedative activities of Epinastine.	Approved, Investigational
Esmirtazapine	Lisdexamfetamine may decrease the sedative activities of Esmirtazapine.	Investigational
Ethopropazine	Lisdexamfetamine may decrease the sedative activities of Ethopropazine.	Approved
Ethosuximide	The therapeutic efficacy of Ethosuximide can be decreased when used in combination with Lisdexamfetamine.	Approved
Ethoxzolamide	Ethoxzolamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Withdrawn
Ethylmorphine	Lisdexamfetamine may increase the analgesic activities of Ethylmorphine.	Approved, Illicit
Etorphine	Lisdexamfetamine may increase the analgesic activities of Etorphine.	Illicit, Vet Approved
Famotidine	Lisdexamfetamine may decrease the sedative activities of Famotidine.	Approved
Fencamfamine	Fencamfamine may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Illicit, Withdrawn
Fentanyl	Lisdexamfetamine may increase the analgesic activities of Fentanyl.	Approved, Illicit, Investigational, Vet Approved
Fexofenadine	Lisdexamfetamine may decrease the sedative activities of Fexofenadine.	Approved
Flunarizine	Lisdexamfetamine may decrease the sedative activities of Flunarizine.	Approved
Flupentixol	Flupentixol may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Withdrawn
Fluphenazine	Fluphenazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Fluspirilene	Fluspirilene may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Furazolidone	Furazolidone may increase the hypertensive activities of Lisdexamfetamine.	Approved, Vet Approved
Glutamic Acid	The serum concentration of Lisdexamfetamine can be decreased when it is combined with L-Glutamic Acid.	Approved, Nutraceutical
Guanethidine	The serum concentration of Lisdexamfetamine can be decreased when it is combined with Guanethidine.	Approved
Haloperidol	Haloperidol may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Heroin	Lisdexamfetamine may increase the analgesic activities of Heroin.	Approved, Illicit
Hydracarbazine	Hydracarbazine may increase the hypertensive activities of Lisdexamfetamine.	Experimental
Hydrocodone	Lisdexamfetamine may increase the analgesic activities of Hydrocodone.	Approved, Illicit
Hydromorphone	Lisdexamfetamine may increase the analgesic activities of Hydromorphone.	Approved, Illicit
Hydroxyzine	Lisdexamfetamine may decrease the sedative activities of Hydroxyzine.	Approved
Iloperidone	Iloperidone may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Imipramine	Imipramine may increase the stimulatory activities of Lisdexamfetamine.	Approved
Ioflupane I-123	Lisdexamfetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.	Approved
Iproclozide	Iproclozide may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Iproniazid	Iproniazid may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Isocarboxazid	Isocarboxazid may increase the hypertensive activities of Lisdexamfetamine.	Approved
Isothipendyl	Lisdexamfetamine may decrease the sedative activities of Isothipendyl.	Approved
Ketobemidone	Lisdexamfetamine may increase the analgesic activities of Ketobemidone.	Approved
Ketotifen	Lisdexamfetamine may decrease the sedative activities of Ketotifen.	Approved
Levocabastine	Lisdexamfetamine may decrease the sedative activities of Levocabastine.	Approved
Levocetirizine	Lisdexamfetamine may decrease the sedative activities of Levocetirizine.	Approved
Levomethadyl Acetate	Lisdexamfetamine may increase the analgesic activities of Levomethadyl Acetate.	Approved
Levorphanol	Lisdexamfetamine may increase the analgesic activities of Levorphanol.	Approved
Lithium	Lithium may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Lodoxamide	Lisdexamfetamine may decrease the sedative activities of Lodoxamide.	Approved
Lofentanil	Lisdexamfetamine may increase the analgesic activities of Lofentanil.	Illicit
Loratadine	Lisdexamfetamine may decrease the sedative activities of Loratadine.	Approved
Loxapine	Loxapine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Lurasidone	Lurasidone may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Magaldrate	Magaldrate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Withdrawn
Magnesium carbonate	Magnesium carbonate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Magnesium Hydroxide	Magnesium hydroxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Magnesium oxide	Magnesium oxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Magnesium Trisilicate	Magnesium Trisilicate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Mebanazine	Mebanazine may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Meclizine	Lisdexamfetamine may decrease the sedative activities of Meclizine.	Approved
Melperone	Melperone may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Mepyramine	Lisdexamfetamine may decrease the sedative activities of Mepyramine.	Approved, Vet Approved
Mequitazine	Lisdexamfetamine may decrease the sedative activities of Mequitazine.	Approved
Mesoridazine	Mesoridazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Methadone	Lisdexamfetamine may increase the analgesic activities of Methadone.	Approved
Methadyl Acetate	Lisdexamfetamine may increase the analgesic activities of Methadyl Acetate.	Approved, Illicit
Methapyrilene	Lisdexamfetamine may decrease the sedative activities of Methapyrilene.	Withdrawn
Methazolamide	Methazolamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.	Approved
Methenamine	The serum concentration of Lisdexamfetamine can be decreased when it is combined with Hexamethylenetetramine.	Approved, Vet Approved
Methotrimeprazine	Methotrimeprazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Methylene blue	Methylene blue may increase the hypertensive activities of Lisdexamfetamine.	Investigational
Metiamide	Lisdexamfetamine may decrease the sedative activities of Metiamide.	Experimental
Mianserin	Lisdexamfetamine may decrease the sedative activities of Mianserin.	Approved
Minaprine	Minaprine may increase the hypertensive activities of Lisdexamfetamine.	Approved
Mirtazapine	Lisdexamfetamine may decrease the sedative activities of Mirtazapine.	Approved
Mizolastine	Lisdexamfetamine may decrease the sedative activities of Mizolastine.	Investigational
Moclobemide	Moclobemide may increase the hypertensive activities of Lisdexamfetamine.	Approved
Molindone	Molindone may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Morphine	Lisdexamfetamine may increase the analgesic activities of Morphine.	Approved, Investigational
Nalbuphine	Lisdexamfetamine may increase the analgesic activities of Nalbuphine.	Approved
Nialamide	Nialamide may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Nizatidine	Lisdexamfetamine may decrease the sedative activities of Nizatidine.	Approved
Normethadone	Lisdexamfetamine may increase the analgesic activities of Normethadone.	Approved, Illicit
Nortriptyline	Nortriptyline may increase the stimulatory activities of Lisdexamfetamine.	Approved
Octamoxin	Octamoxin may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Olanzapine	Olanzapine may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Investigational
Olopatadine	Lisdexamfetamine may decrease the sedative activities of Olopatadine.	Approved
Ondansetron	Ondansetron may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Opipramol	Opipramol may increase the stimulatory activities of Lisdexamfetamine.	Investigational
Opium	Lisdexamfetamine may increase the analgesic activities of Opium.	Approved, Illicit
Osanetant	Osanetant may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Oxycodone	Lisdexamfetamine may increase the analgesic activities of Oxycodone.	Approved, Illicit, Investigational
Oxymorphone	Lisdexamfetamine may increase the analgesic activities of Oxymorphone.	Approved, Investigational, Vet Approved
Ozagrel	Lisdexamfetamine may decrease the sedative activities of Kct 0809.	Investigational
Paliperidone	Paliperidone may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Pargyline	Pargyline may increase the hypertensive activities of Lisdexamfetamine.	Approved
Pemirolast	Lisdexamfetamine may decrease the sedative activities of Pemirolast.	Approved
Pentazocine	Lisdexamfetamine may increase the analgesic activities of Pentazocine.	Approved, Vet Approved
Perazine	Perazine may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Perospirone	Perospirone may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Perphenazine	Perphenazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Pethidine	Lisdexamfetamine may increase the analgesic activities of Pethidine.	Approved
Phenelzine	Phenelzine may increase the hypertensive activities of Lisdexamfetamine.	Approved
Phenindamine	Lisdexamfetamine may decrease the sedative activities of Phenindamine.	Approved
Pheniprazine	Pheniprazine may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Pheniramine	Lisdexamfetamine may decrease the sedative activities of Pheniramine.	Approved
Phenobarbital	The serum concentration of Phenobarbital can be decreased when it is combined with Lisdexamfetamine.	Approved
Phenoxypropazine	Phenoxypropazine may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Phenytoin	The serum concentration of Phenytoin can be decreased when it is combined with Lisdexamfetamine.	Approved, Vet Approved
Pimozide	Pimozide may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Pipamperone	Pipamperone may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Pipotiazine	Pipotiazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Piritramide	Lisdexamfetamine may increase the analgesic activities of Piritramide.	Investigational
Pirlindole	Pirlindole may increase the hypertensive activities of Lisdexamfetamine.	Approved
Pivhydrazine	Pivhydrazine may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Prochlorperazine	Prochlorperazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Vet Approved
Promazine	Promazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Vet Approved
Promethazine	Lisdexamfetamine may decrease the sedative activities of Promethazine.	Approved
Propericiazine	Propericiazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Prothipendyl	Prothipendyl may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Protriptyline	Protriptyline may increase the stimulatory activities of Lisdexamfetamine.	Approved
Quetiapine	Quetiapine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Raclopride	Raclopride may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Ranitidine	Lisdexamfetamine may decrease the sedative activities of Ranitidine.	Approved
Rasagiline	Rasagiline may increase the hypertensive activities of Lisdexamfetamine.	Approved
Remifentanil	Lisdexamfetamine may increase the analgesic activities of Remifentanil.	Approved
Remoxipride	Remoxipride may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Withdrawn
Reserpine	Reserpine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Risperidone	Risperidone may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Investigational
Ritanserin	Ritanserin may decrease the stimulatory activities of Lisdexamfetamine.	Investigational
Roxatidine acetate	Lisdexamfetamine may decrease the sedative activities of Roxatidine acetate.	Approved
Safrazine	Safrazine may increase the hypertensive activities of Lisdexamfetamine.	Withdrawn
Selegiline	Selegiline may increase the hypertensive activities of Lisdexamfetamine.	Approved, Investigational, Vet Approved
Sertindole	Sertindole may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Withdrawn
Spaglumic Acid	Lisdexamfetamine may decrease the sedative activities of Spaglumic Acid.	Approved
Sufentanil	Lisdexamfetamine may increase the analgesic activities of Sufentanil.	Approved, Investigational
Sulpiride	Sulpiride may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Tapentadol	Lisdexamfetamine may increase the analgesic activities of Tapentadol.	Approved
Terfenadine	Lisdexamfetamine may decrease the sedative activities of Terfenadine.	Withdrawn
Tesmilifene	Lisdexamfetamine may decrease the sedative activities of Tesmilifene.	Investigational
Thioproperazine	Thioproperazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Thioridazine	Thioridazine may decrease the stimulatory activities of Lisdexamfetamine.	Withdrawn
Thiothixene	Thiothixene may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Tianeptine	Tianeptine may increase the stimulatory activities of Lisdexamfetamine.	Approved
Tiapride	Tiapride may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Investigational
Toloxatone	Toloxatone may increase the hypertensive activities of Lisdexamfetamine.	Approved
Tramadol	Lisdexamfetamine may increase the analgesic activities of Tramadol.	Approved, Investigational
Tranilast	Lisdexamfetamine may decrease the sedative activities of Tranilast.	Approved, Investigational
Trans-2-Phenylcyclopropylamine	Trans-2-Phenylcyclopropylamine may increase the hypertensive activities of Lisdexamfetamine.	Experimental
Tranylcypromine	Tranylcypromine may increase the hypertensive activities of Lisdexamfetamine.	Approved
Trifluoperazine	Trifluoperazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Triflupromazine	Triflupromazine may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Vet Approved
Trimipramine	Trimipramine may increase the stimulatory activities of Lisdexamfetamine.	Approved
Tripelennamine	Lisdexamfetamine may decrease the sedative activities of Tripelennamine.	Approved, Vet Approved
Triprolidine	Lisdexamfetamine may decrease the sedative activities of Triprolidine.	Approved
Vitamin C	The serum concentration of Lisdexamfetamine can be decreased when it is combined with Vitamin C.	Approved, Nutraceutical
Ziprasidone	Ziprasidone may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Zotepine	Zotepine may decrease the stimulatory activities of Lisdexamfetamine.	Approved
Zuclopenthixol	Zuclopenthixol may decrease the stimulatory activities of Lisdexamfetamine.	Approved, Investigational

Food Interactions

Not 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

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 ]
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 ]
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

Resource	Link
Human Metabolome Database (HMDB)	HMDB15385
PubChem Compound	11597698
PubChem Substance	46505358
ChemSpider	9772458
ChEBI	135925
ChEMBL	CHEMBL1201222
Therapeutic Targets Database	DAP000571
PharmGKB	PA164748975
Drug Product Database	20437
RxList	http://www.rxlist.com/cgi/generic/vyvanse.htm
Drugs.com	http://www.drugs.com/cdi/lisdexamfetamine.html
Wikipedia	Lisdexamfetamine

ATC Codes

N06BA12 — Lisdexamfetamine

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Active Not Recruiting	Treatment	Methamphetamine Dependence	1
1	Completed	Not Available	Attention-Deficit Hyperactivity Disorder (ADHD)	1
1	Completed	Not Available	Healthy Volunteers	2
1	Completed	Not Available	Schizophrenic Disorders	1
1	Completed	Basic Science	Healthy Volunteers	1
1	Completed	Treatment	Drug Users / Healthy Volunteers	1
1	Completed	Treatment	Healthy Volunteers	1
1	Terminated	Not Available	Healthy Volunteers	1
1, 2	Completed	Basic Science	Adhd	1
1, 2	Completed	Treatment	Amphetamine-Related Disorders / Attention Deficit Disorder With Hyperactivity / Substance-Related Disorders	1
1, 2	Completed	Treatment	Dependence, Cocaine	2
2	Active Not Recruiting	Treatment	Attention Deficit Hyperactivity Disorder (ADHD) / Deficient Emotional Self-Regulation (DESR)	1
2	Completed	Not Available	Sleep Deprivation	1
2	Completed	Treatment	Amphetamine-Related Disorders / Attention Deficit Disorder With Hyperactivity / Substance-Related Disorders	1
2	Completed	Treatment	Attention Deficit Disorder With Hyperactivity	1
2	Completed	Treatment	Binge Eating Disorder (BED)	1
2	Completed	Treatment	Dependence, Cocaine	1
2	Completed	Treatment	Disseminated Sclerosis	1
2	Completed	Treatment	Major Depressive Disorder (MDD)	3
2	Completed	Treatment	Schizophrenia and Predominant Negative Symptoms	1
2	Completed	Treatment	Severe Mood Dysregulation	1
2	Recruiting	Not Available	Binge Eating Disorder (BED)	1
2	Recruiting	Treatment	Attention Deficit Disorder (ADD) / Attention Deficit Hyperactivity Disorder (ADHD)	1
3	Completed	Not Available	Adhd	1
3	Completed	Treatment	Adhd	5
3	Completed	Treatment	Attention Deficit Disorder (ADD) / Traumatic Brain Injury (TBI)	1
3	Completed	Treatment	Attention Deficit Disorders With Hyperactivity / Attention Deficit Hyperactivity Disorder (ADHD)	1
3	Completed	Treatment	Attention Deficit Hyperactivity Disorder (ADHD)	2
3	Completed	Treatment	Attention-Deficit/Hyperactivity Disorder	1
3	Completed	Treatment	Binge Eating Disorder (BED)	5
3	Completed	Treatment	Major Depressive Disorder (MDD)	2
3	Recruiting	Treatment	Attention Deficit Hyperactivity Disorder (ADHD) / Attention-Deficit/Hyperactivity Disorder	1
3	Terminated	Treatment	BiPolar / Depressive State	1
3	Terminated	Treatment	Depression, Bipolar	1
3	Terminated	Treatment	Major Depressive Disorder (MDD)	1
4	Active Not Recruiting	Treatment	Adult Attention Deficit Hyperactivity Disorder (ADHD) With Co-occuring Anxiety and Depressive Disorders	1
4	Completed	Not Available	Attention Deficit Hyperactivity Disorder (ADHD)	2
4	Completed	Basic Science	Attention Deficit Hyperactivity Disorder (ADHD)	1
4	Completed	Basic Science	Attention Deficit/Hyperactivity Disorder	1
4	Completed	Treatment	ADHD Specifically With Executive Function Impairment	1
4	Completed	Treatment	Adhd	1
4	Completed	Treatment	Attention Deficit Disorder With Hyperactivity	1
4	Completed	Treatment	Attention Deficit Hyperactivity Disorder (ADHD)	3
4	Completed	Treatment	Attention Deficit Hyperactivity Disorder (ADHD) / Deficient Emotional Self-Regulation (DESR)	1
4	Completed	Treatment	Attention Deficit/Hyperactivity Disorder (ADHD)	1
4	Completed	Treatment	Attention-Deficit/Hyperactivity Disorder	4
4	Completed	Treatment	Brain Activity / Cognition / Menopause	1
4	Completed	Treatment	Cognitive Impairments / Myalgic Encephalomyelitis (ME)	1
4	Completed	Treatment	Cognitive Impairments / Symptomatic Menopause	1
4	Completed	Treatment	Major Depressive Disorder (MDD)	1
4	Not Yet Recruiting	Other	Lisdexamfetamine	1
4	Not Yet Recruiting	Treatment	Cognitive Impairments / RRSO	1
4	Recruiting	Treatment	Adhd / Attention Deficit/Hyperactivity Disorder (ADHD)	1
4	Recruiting	Treatment	Attention Deficit Disorder (ADD) / Traumatic Brain Injury (TBI)	1
4	Recruiting	Treatment	Attention Deficit Hyperactivity Disorder (ADHD)	2
4	Terminated	Treatment	Attention Deficit Hyperactivity Disorder (ADHD) / BMI >30 kg/m2 / Glucose tolerance impaired	1
4	Terminated	Treatment	Depression, Bipolar	1
4	Unknown Status	Basic Science	Adhd	1
Not Available	Active Not Recruiting	Treatment	Attention Deficit Hyperactivity Disorder (ADHD)	1
Not Available	Completed	Not Available	Attention Deficit/Hyperactivity Disorder / Bipolar Disorder (BD)	1
Not Available	Completed	Treatment	Attention Deficit Hyperactivity Disorder (ADHD) / Nicotine Dependence	1
Not Available	Completed	Treatment	Attention Deficit Hyperactivity Disorder (ADHD) / Sleep	1
Not Available	Recruiting	Treatment	Attention Deficit Hyperactivity Disorder (ADHD)	4
Not Available	Withdrawn	Prevention	Planned RRSO	1
Not Available	Withdrawn	Treatment	Cognitive Impairments / RRSO	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Dosage forms

Form	Route	Strength
Capsule	Oral	10 mg/1
Capsule	Oral	10 mg
Capsule	Oral	20 mg/1
Capsule	Oral	20 mg
Capsule	Oral	30 mg
Capsule	Oral	30 mg/1
Capsule	Oral	40 mg
Capsule	Oral	40 mg/1
Capsule	Oral	50 mg
Capsule	Oral	50 mg/1
Capsule	Oral	60 mg
Capsule	Oral	60 mg/1
Capsule	Oral	70 mg/1
Capsule	Oral	70 mg
Tablet, chewable	Oral	10 mg/1
Tablet, chewable	Oral	20 mg/1
Tablet, chewable	Oral	30 mg/1
Tablet, chewable	Oral	40 mg/1
Tablet, chewable	Oral	50 mg/1
Tablet, chewable	Oral	60 mg/1

Prices

Unit description	Cost	Unit
Vyvanse 30 mg capsule	6.24USD	capsule
Vyvanse 50 mg capsule	6.02USD	capsule
Vyvanse 70 mg capsule	5.85USD	capsule
Vyvanse 40 mg capsule	5.8USD	capsule
Vyvanse 20 mg capsule	5.26USD	capsule
Vyvanse 60 mg capsule	5.02USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US7105486	No	2003-02-24	2023-02-24	US
US7223735	No	2003-02-24	2023-02-24	US
US7655630	No	2003-02-24	2023-02-24	US
US7659253	No	2003-02-24	2023-02-24	US
US7659254	No	2003-02-24	2023-02-24	US
US7662787	No	2003-02-24	2023-02-24	US
US7662788	No	2003-02-24	2023-02-24	US
US7671030	No	2003-02-24	2023-02-24	US
US7671031	No	2003-02-24	2023-02-24	US
US7674774	No	2003-02-24	2023-02-24	US
US7678770	No	2003-02-24	2023-02-24	US
US7678771	No	2003-02-24	2023-02-24	US
US7687466	No	2003-02-24	2023-02-24	US
US7687467	No	2003-02-24	2023-02-24	US
US7700561	No	2003-02-24	2023-02-24	US
US7713936	No	2003-02-24	2023-02-24	US
US7718619	No	2003-02-24	2023-02-24	US
US7723305	No	2003-02-24	2023-02-24	US

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	792 mg/mL (dimesylate salt)	Not Available
logP	1.06	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0877 mg/mL	ALOGPS
logP	1.01	ALOGPS
logP	1.14	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	15.89	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.14 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	78.31 m³·mol^-1	ChemAxon
Polarizability	31.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9858
Blood Brain Barrier	+	0.9444
Caco-2 permeable	+	0.664
P-glycoprotein substrate	Substrate	0.6919
P-glycoprotein inhibitor I	Non-inhibitor	0.9264
P-glycoprotein inhibitor II	Non-inhibitor	0.9802
Renal organic cation transporter	Non-inhibitor	0.8398
CYP450 2C9 substrate	Non-substrate	0.8303
CYP450 2D6 substrate	Non-substrate	0.621
CYP450 3A4 substrate	Non-substrate	0.7228
CYP450 1A2 substrate	Non-inhibitor	0.7025
CYP450 2C9 inhibitor	Non-inhibitor	0.9337
CYP450 2D6 inhibitor	Non-inhibitor	0.858
CYP450 2C19 inhibitor	Non-inhibitor	0.7568
CYP450 3A4 inhibitor	Non-inhibitor	0.5499
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8494
Ames test	Non AMES toxic	0.7156
Carcinogenicity	Non-carcinogens	0.854
Biodegradation	Not ready biodegradable	0.8575
Rat acute toxicity	2.0058 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9688
hERG inhibition (predictor II)	Non-inhibitor	0.9004

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organic acids and derivatives

Sub Class

Carboxylic acids and derivatives

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

Substituents

Alpha-amino acid amide / Amphetamine or derivatives / Phenylpropane / Monocyclic benzene moiety / Fatty amide / Fatty acyl / Benzenoid / N-acyl-amine / Carboxamide group / Secondary carboxylic acid amide

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Targets

Details

1. Alpha-1B adrenergic receptor

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

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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Details

2. Sodium-dependent dopamine transporter

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

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 ]

Drug created on May 14, 2007 19:24 / Updated on July 22, 2017 18:08

Get DrugBank to go!

Structure for DB01255 (Lisdexamfetamine)

Targets

References

References