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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyLisdexamfetamine
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
Structure for DB01255 (Lisdexamfetamine)
- Synonyms
- Lisdexamfetamine
- lisdexamfetamine dimesylate
- NRP104
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Vyvanse Capsule 20 mg/1 Oral Shire 2007-12-10 Not applicable US 
Vyvanse Capsule 70 mg/1 Oral Shire 2007-02-23 Not applicable US Vyvanse Capsule 70 mg Oral Shire Pharma Canada Ulc 2017-01-05 Not applicable Canada 
Vyvanse Capsule 50 mg Oral Shire Pharma Canada Ulc 2009-08-04 Not applicable Canada Vyvanse Capsule 20 mg/1 Oral Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc 2007-12-10 2018-03-22 US Vyvanse Tablet, chewable 50 mg/1 Oral Shire 2017-01-28 Not applicable US Vyvanse Capsule 70 mg/1 Oral Avera Mc Kennan Hospital 2015-09-30 Not applicable US Vyvanse Capsule 50 mg/1 Oral Physicians Total Care, Inc. 2008-07-11 Not applicable US Vyvanse Capsule 40 mg/1 Oral Shire 2007-12-10 Not applicable US Vyvanse Tablet, chewable 20 mg/1 Oral Shire 2017-01-28 Not applicable US - Categories
- Alpha1 Antagonists
- Amines
- Amphetamine
- Amphetamines
- Central Nervous System Agents
- Central Nervous System Stimulants
- Centrally Acting Sympathomimetics
- Dextroamphetamine
- Dopamine Agents
- Dopamine Uptake Inhibitors
- Ethylamines
- Membrane Transport Modulators
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Phenethylamines
- Psychoanaleptics
- Psychostimulants, Agents Used for Adhd and Nootropics
- 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[[email protected]@H](CC1=CC=CC=C1)NC(=O)[[email protected]@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 Actions Organism UAlpha-1B adrenergic receptor antagonistHuman ASodium-dependent dopamine transporter inhibitorHuman - 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 Almasilate Almasilate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Experimental Aloglutamol Aloglutamol may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved Alphacetylmethadol Lisdexamfetamine may increase the analgesic activities of Alphacetylmethadol. Experimental, Illicit Alphaprodine Lisdexamfetamine may increase the analgesic activities of Alphaprodine. Illicit Aluminium Aluminium may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Investigational Aluminium acetoacetate Aluminium acetoacetate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Experimental Aluminium glycinate Aluminium glycinate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Experimental Aluminum hydroxide Aluminum hydroxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Investigational 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, Investigational, Vet Approved Amoxapine Amoxapine may increase the stimulatory activities of Lisdexamfetamine. Approved Amperozide Amperozide may decrease the stimulatory activities of Lisdexamfetamine. Experimental Amphetamine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Amphetamine. Approved, Illicit, Investigational 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 Azaperone Azaperone may decrease the stimulatory activities of Lisdexamfetamine. Investigational, Vet Approved Azatadine Lisdexamfetamine may decrease the sedative activities of Azatadine. Approved Azelastine Lisdexamfetamine may decrease the sedative activities of Azelastine. Approved Bamipine Lisdexamfetamine may decrease the sedative activities of Bamipine. Experimental Benmoxin The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Benmoxin. Withdrawn Benperidol Benperidol may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Benzatropine Lisdexamfetamine may decrease the sedative activities of Benzatropine. Approved 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, Investigational Bismuth subnitrate Bismuth subnitrate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Experimental Brexpiprazole Brexpiprazole may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Brofaromine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Brofaromine. Experimental Bromperidol Bromperidol may decrease the stimulatory activities of Lisdexamfetamine. Approved, 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 Butaperazine Butaperazine may decrease the stimulatory activities of Lisdexamfetamine. Experimental Butorphanol Lisdexamfetamine may increase the analgesic activities of Butorphanol. Approved, Illicit, Vet Approved Butyric Acid Lisdexamfetamine may decrease the sedative activities of Butyric Acid. Experimental, Investigational Calcium Carbonate Calcium Carbonate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Investigational Calcium silicate Calcium silicate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Experimental Carbinoxamine Lisdexamfetamine may decrease the sedative activities of Carbinoxamine. Approved Carfentanil Lisdexamfetamine may increase the analgesic activities of Carfentanil. Illicit, Investigational, Vet Approved Cariprazine Cariprazine may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Caroxazone The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Caroxazone. 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 Chlorproethazine Chlorproethazine may decrease the stimulatory activities of Lisdexamfetamine. Experimental Chlorpromazine Chlorpromazine may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational, Vet Approved Chlorprothixene Chlorprothixene may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational, Withdrawn Cimetidine Lisdexamfetamine may decrease the sedative activities of Cimetidine. Approved, Investigational Cinnarizine Lisdexamfetamine may decrease the sedative activities of Cinnarizine. Approved, Investigational Clemastine Lisdexamfetamine may decrease the sedative activities of Clemastine. Approved, Investigational Clomipramine Clomipramine may increase the stimulatory activities of Lisdexamfetamine. Approved, Investigational, Vet Approved Clopenthixol Clopenthixol may decrease the stimulatory activities of Lisdexamfetamine. Experimental Clothiapine Clothiapine may decrease the stimulatory activities of Lisdexamfetamine. Experimental 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, Investigational Desloratadine Lisdexamfetamine may decrease the sedative activities of Desloratadine. Approved, Investigational Dexbrompheniramine Lisdexamfetamine may decrease the sedative activities of Dexbrompheniramine. Approved Dexchlorpheniramine Lisdexamfetamine may decrease the sedative activities of Dexchlorpheniramine. Experimental, Investigational 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, Investigational, Withdrawn Dezocine Lisdexamfetamine may increase the analgesic activities of Dezocine. Approved, Investigational Dibenzepin Dibenzepin may increase the stimulatory activities of Lisdexamfetamine. Experimental Diclofenamide Diclofenamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Investigational 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, Investigational Dimetotiazine Lisdexamfetamine may decrease the sedative activities of Dimetotiazine. Approved Diphenhydramine Lisdexamfetamine may decrease the sedative activities of Diphenhydramine. Approved, Investigational Diphenoxylate Lisdexamfetamine may increase the analgesic activities of Diphenoxylate. Approved, Illicit Dixyrazine Dixyrazine may decrease the stimulatory activities of Lisdexamfetamine. Experimental Dosulepin Dosulepin may increase the stimulatory activities of Lisdexamfetamine. Approved Doxepin Lisdexamfetamine may decrease the sedative activities of Doxepin. Approved, Investigational Doxylamine Lisdexamfetamine may decrease the sedative activities of Doxylamine. Approved, Vet Approved DPDPE Lisdexamfetamine may increase the analgesic activities of DPDPE. Experimental Droperidol Droperidol may decrease the stimulatory activities of Lisdexamfetamine. Approved, Vet Approved Ebastine Lisdexamfetamine may decrease the sedative activities of Ebastine. Approved, 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 Lisdexamfetamine can cause a decrease in the absorption of Ethosuximide resulting in a reduced serum concentration and potentially a decrease in efficacy. 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, Investigational Fluanisone Fluanisone may decrease the stimulatory activities of Lisdexamfetamine. Experimental Flunarizine Lisdexamfetamine may decrease the sedative activities of Flunarizine. Approved Flupentixol Flupentixol may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational, Withdrawn Fluphenazine Fluphenazine may decrease the stimulatory activities of Lisdexamfetamine. Approved Fluspirilene Fluspirilene may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Furazolidone Furazolidone may increase the hypertensive activities of Lisdexamfetamine. Approved, Investigational, Vet Approved Glutamic Acid The serum concentration of Lisdexamfetamine can be decreased when it is combined with 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 Harmaline The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Harmaline. Experimental Heroin Lisdexamfetamine may increase the analgesic activities of Heroin. Approved, Illicit, Investigational Hydracarbazine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Hydracarbazine. Experimental Hydrocodone Lisdexamfetamine may increase the analgesic activities of Hydrocodone. Approved, Illicit Hydromorphone Lisdexamfetamine may increase the analgesic activities of Hydromorphone. Approved, Illicit Hydrotalcite Hydrotalcite may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Experimental, Investigational 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 Iprindole Iprindole may increase the stimulatory activities of Lisdexamfetamine. Experimental Iproclozide The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Iproclozide. 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, Investigational Ketotifen Lisdexamfetamine may decrease the sedative activities of Ketotifen. Approved Lafutidine Lisdexamfetamine may decrease the sedative activities of Lafutidine. Investigational Lavoltidine Lisdexamfetamine may decrease the sedative activities of Lavoltidine. Investigational Levocabastine Lisdexamfetamine may decrease the sedative activities of Levocabastine. Approved, Investigational Levocetirizine Lisdexamfetamine may decrease the sedative activities of Levocetirizine. Approved Levomethadyl Acetate Lisdexamfetamine may increase the analgesic activities of Levomethadyl Acetate. Approved, Investigational 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 Lofepramine Lofepramine may increase the stimulatory activities of Lisdexamfetamine. Experimental Loratadine Lisdexamfetamine may decrease the sedative activities of Loratadine. Approved, Investigational Loxapine Loxapine may decrease the stimulatory activities of Lisdexamfetamine. Approved Lurasidone Lurasidone may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Magaldrate Magaldrate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Withdrawn Magnesium hydroxide Magnesium hydroxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Investigational Magnesium oxide Magnesium oxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved Magnesium peroxide Magnesium peroxide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Experimental Magnesium silicate Magnesium silicate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved, Experimental Magnesium Trisilicate Magnesium Trisilicate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved Mebanazine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Mebanazine. Withdrawn Meclizine Lisdexamfetamine may decrease the sedative activities of Meclizine. Approved Melperone Melperone may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Meptazinol Lisdexamfetamine may increase the analgesic activities of Meptazinol. Experimental 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, Investigational 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 Methenamine. Approved, Vet Approved Methotrimeprazine Methotrimeprazine may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Methylene blue The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Methylene blue. Approved, Investigational Metiamide Lisdexamfetamine may decrease the sedative activities of Metiamide. Experimental Mianserin Lisdexamfetamine may decrease the sedative activities of Mianserin. Approved, Investigational 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, Investigational Molindone Molindone may decrease the stimulatory activities of Lisdexamfetamine. Approved Moperone Moperone may decrease the stimulatory activities of Lisdexamfetamine. Experimental Morphine Lisdexamfetamine may increase the analgesic activities of Morphine. Approved, Investigational Mosapramine Mosapramine may decrease the stimulatory activities of Lisdexamfetamine. Experimental Nalbuphine Lisdexamfetamine may increase the analgesic activities of Nalbuphine. Approved Nialamide Nialamide may increase the hypertensive activities of Lisdexamfetamine. Withdrawn Nicomorphine Lisdexamfetamine may increase the analgesic activities of Nicomorphine. Experimental 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 The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Octamoxin. 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 Oxatomide Lisdexamfetamine may decrease the sedative activities of Oxatomide. 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 Oxypertine Oxypertine may decrease the stimulatory activities of Lisdexamfetamine. Experimental Ozagrel Lisdexamfetamine may decrease the sedative activities of Ozagrel. 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, Investigational Penfluridol Penfluridol may decrease the stimulatory activities of Lisdexamfetamine. Experimental Pentazocine Lisdexamfetamine may increase the analgesic activities of Pentazocine. Approved, Vet Approved Perazine Perazine may decrease the stimulatory activities of Lisdexamfetamine. Approved, 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 Phenazocine Lisdexamfetamine may increase the analgesic activities of Phenazocine. Experimental Phenelzine Phenelzine may increase the hypertensive activities of Lisdexamfetamine. Approved Phenindamine Lisdexamfetamine may decrease the sedative activities of Phenindamine. Approved Pheniprazine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Pheniprazine. 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, Investigational Phenoperidine Lisdexamfetamine may increase the analgesic activities of Phenoperidine. Experimental Phenoxypropazine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Phenoxypropazine. 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, Investigational Pipotiazine Pipotiazine may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Piritramide Lisdexamfetamine may increase the analgesic activities of Piritramide. Approved, Investigational Pirlindole Pirlindole may increase the hypertensive activities of Lisdexamfetamine. Approved Pivhydrazine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Pivhydrazine. Withdrawn Procarbazine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Procarbazine. Approved, Investigational 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, Investigational Propericiazine Propericiazine may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational 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 Quifenadine Lisdexamfetamine may decrease the sedative activities of Quifenadine. Experimental 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, Investigational 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, Investigational Safrazine The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Safrazine. Withdrawn Selegiline The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Selegiline. Approved, Investigational, Vet Approved Sertindole Sertindole may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational, Withdrawn Sodium bicarbonate Sodium bicarbonate may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved Sufentanil Lisdexamfetamine may increase the analgesic activities of Sufentanil. Approved, Investigational Sulpiride Sulpiride may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Sultopride Sultopride may decrease the stimulatory activities of Lisdexamfetamine. Experimental Tapentadol Lisdexamfetamine may increase the analgesic activities of Tapentadol. Approved Terfenadine Lisdexamfetamine may decrease the sedative activities of Terfenadine. Approved, Withdrawn Tesmilifene Lisdexamfetamine may decrease the sedative activities of Tesmilifene. Investigational Tetrahydropalmatine Tetrahydropalmatine may decrease the stimulatory activities of Lisdexamfetamine. Investigational Thiopropazate Thiopropazate may decrease the stimulatory activities of Lisdexamfetamine. Experimental Thioproperazine Thioproperazine may decrease the stimulatory activities of Lisdexamfetamine. Approved Thioridazine Thioridazine may decrease the stimulatory activities of Lisdexamfetamine. Approved, Withdrawn Thiothixene Thiothixene may decrease the stimulatory activities of Lisdexamfetamine. Approved Thonzylamine Lisdexamfetamine may decrease the sedative activities of Thonzylamine. Approved Tianeptine Tianeptine may increase the stimulatory activities of Lisdexamfetamine. Approved, Investigational Tiapride Tiapride may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Tilidine Lisdexamfetamine may increase the analgesic activities of Tilidine. Experimental 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 Tranylcypromine Tranylcypromine may increase the hypertensive activities of Lisdexamfetamine. Approved, Investigational Trifluoperazine Trifluoperazine may decrease the stimulatory activities of Lisdexamfetamine. Approved, Investigational Trifluperidol Trifluperidol may decrease the stimulatory activities of Lisdexamfetamine. Experimental 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 Tritoqualine Lisdexamfetamine may decrease the sedative activities of Tritoqualine. Experimental Tromethamine Tromethamine may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level. Approved Veralipride Veralipride may decrease the stimulatory activities of Lisdexamfetamine. Experimental 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, Investigational, Withdrawn 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
- Human Metabolome Database
- HMDB0015385
- PubChem Compound
- 11597698
- PubChem Substance
- 46505358
- ChemSpider
- 9772458
- ChEBI
- 135925
- ChEMBL
- CHEMBL1201222
- Therapeutic Targets Database
- DAP000571
- PharmGKB
- PA164748975
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Lisdexamfetamine
- ATC Codes
- N06BA12 — Lisdexamfetamine
- AHFS Codes
- 28:20.04 — Amphetamines
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- New River Pharmaceuticals Inc.
- Patheon Inc.
- Physicians Total Care Inc.
- Quality Care
- Shire Inc.
- 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) US7659253 No 2003-02-24 2023-02-24 US US7718619 No 2003-02-24 2023-02-24 US US7659254 No 2003-02-24 2023-02-24 US US7671030 No 2003-02-24 2023-02-24 US US7662788 No 2003-02-24 2023-02-24 US US7687467 No 2003-02-24 2023-02-24 US US7678770 No 2003-02-24 2023-02-24 US US7671031 No 2003-02-24 2023-02-24 US US7713936 No 2003-02-24 2023-02-24 US US7674774 No 2003-02-24 2023-02-24 US US7678771 No 2003-02-24 2023-02-24 US US7655630 No 2003-02-24 2023-02-24 US US7687466 No 2003-02-24 2023-02-24 US US7223735 No 2003-02-24 2023-02-24 US US7700561 No 2003-02-24 2023-02-24 US US7662787 No 2003-02-24 2023-02-24 US US7723305 No 2003-02-24 2023-02-24 US US7105486 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- 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
- 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
- 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) prot...
- Gene Name
- ADRA1B
- Uniprot ID
- P35368
- Uniprot Name
- Alpha-1B adrenergic receptor
- 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]
- 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
- Uniprot Name
- Sodium-dependent dopamine transporter
- 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 April 23, 2018 23:08