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

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

Structure

Similar Structures

Synonyms

Lisdexamfetamine

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Lisdexamfetamine dimesylate	SJT761GEGS	608137-33-3	CETWSOHVEGTIBR-FORAGAHYSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Vyvanse	Tablet, chewable	20 mg/1	Oral	Shire LLC	2017-01-28	Not applicable
Vyvanse	Capsule	40 mg/1	Oral	Shire LLC	2007-12-10	Not applicable
Vyvanse	Capsule	10 mg/1	Oral	Avera McKennan Hospital	2015-03-26	2018-06-07
Vyvanse	Tablet, chewable	30 mg	Oral	Shire Pharma Canada Ulc	2019-08-06	Not applicable
Vyvanse	Capsule	30 mg/1	Oral	Physicians Total Care, Inc.	2008-07-11	Not applicable
Vyvanse	Capsule	60 mg	Oral	Shire Pharma Canada Ulc	2010-04-14	Not applicable
Vyvanse	Tablet, chewable	60 mg/1	Oral	Shire LLC	2017-01-28	Not applicable
Vyvanse	Tablet, chewable	10 mg/1	Oral	Shire LLC	2017-01-28	Not applicable
Vyvanse	Capsule	30 mg/1	Oral	Shire LLC	2007-02-23	Not applicable
Vyvanse	Capsule	70 mg/1	Oral	Avera McKennan Hospital	2015-09-30	2018-05-25

Additional Data Available

Application Number

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

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Product Code

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

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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) and for moderate to severe binge eating disorder in adults ^Label, ⁴.

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

Associated Conditions

Pharmacodynamics

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

Mechanism of action

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

Target	Actions	Organism
UTrace amine-associated receptor 1	agonist	Humans

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

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

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

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

Volume of distribution

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

Protein binding

Not Available

Metabolism

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

Lisdexamfetamine
L-Lysine and Dextroamphetamine

Route of elimination

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

Half life

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

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

Clearance

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

Toxicity

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

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

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

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

Use in Pregnancy

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

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine	The metabolism of Lisdexamfetamine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	The risk or severity of hypertension can be increased when Lisdexamfetamine is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazole	The therapeutic efficacy of 1-benzylimidazole can be decreased when used in combination with Lisdexamfetamine.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of serotonin syndrome can be increased when Lisdexamfetamine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of serotonin syndrome can be increased when Lisdexamfetamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthine	The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acid	The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with 3,5-diiodothyropropionic acid.
3,5-Diiodotyrosine	The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with 3,5-Diiodotyrosine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of serotonin syndrome can be increased when Lisdexamfetamine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The risk or severity of hypertension can be increased when Lisdexamfetamine is combined with 4-Methoxyamphetamine.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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]
Goodman DW: Lisdexamfetamine dimesylate (vyvanse), a prodrug stimulant for attention-deficit/hyperactivity disorder. P T. 2010 May;35(5):273-87. [PubMed:20514273]
Miller GM: The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity. J Neurochem. 2011 Jan;116(2):164-76. doi: 10.1111/j.1471-4159.2010.07109.x. [PubMed:21073468]
Liu JF, Li JX: TAAR1 in Addiction: Looking Beyond the Tip of the Iceberg. Front Pharmacol. 2018 Mar 27;9:279. doi: 10.3389/fphar.2018.00279. eCollection 2018. [PubMed:29636691]
Pei Y, Asif-Malik A, Canales JJ: Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications. Front Neurosci. 2016 Apr 5;10:148. doi: 10.3389/fnins.2016.00148. eCollection 2016. [PubMed:27092049]
Vyvanse, Canadian Monograph [File]
EPAR: Lisdexamfetamine dimesylate [File]
WHO Summary: Lisdexamfetamine [File]

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

FDA label

Download (371 KB)

MSDS

Download (33.8 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Active Not Recruiting	Treatment	Methamphetamine Dependence	1
1	Completed	Not Available	Attention Deficit Disorder With Hyperactivity (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	2
1	Terminated	Not Available	Healthy Volunteers	1
1	Terminated	Basic Science	Dependence, Cocaine	1
1, 2	Completed	Basic Science	Attention Deficit Disorder With Hyperactivity (ADHD)	1
1, 2	Completed	Treatment	Amphetamine-Related Disorders / Attention Deficit Disorder With Hyperactivity / Substance-Related Disorders	1
1, 2	Completed	Treatment	Dependence, Cocaine	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 (ADD) / Attention Deficit Disorder With Hyperactivity (ADHD)	1
2	Completed	Treatment	Attention Deficit Disorder With Hyperactivity	1
2	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD)	1
2	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / Deficient Emotional Self-Regulation (DESR)	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	Bulimia Nervosa (BN)	1
3	Active Not Recruiting	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / Attention-Deficit/Hyperactivity Disorder	1
3	Completed	Not Available	Attention Deficit Disorder With Hyperactivity (ADHD)	1
3	Completed	Treatment	Attention Deficit Disorder (ADD) / Traumatic Brain Injury (TBI)	1
3	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD)	8
3	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / Attention Deficit Disorders With Hyperactivity	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	Binge Eating Disorder (BED) / BMI >30 kg/m2	1
3	Terminated	Treatment	Bipolar / Depression	1
3	Terminated	Treatment	Depression, Bipolar	1
3	Terminated	Treatment	Major Depressive Disorder (MDD)	1
3	Terminated	Treatment	Schizophrenic Disorders	3
3	Unknown Status	Not Available	Attention Deficit Disorder With Hyperactivity (ADHD)	1
3	Withdrawn	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD)	1
3	Withdrawn	Treatment	Negative Symptoms of Schizophrenia	1
4	Completed	Not Available	Attention Deficit Disorder With Hyperactivity (ADHD)	2
4	Completed	Basic Science	Attention Deficit Disorder With Hyperactivity (ADHD)	2
4	Completed	Basic Science	Attention Deficit/Hyperactivity Disorder	1
4	Completed	Treatment	ADHD Specifically With Executive Function Impairment	1
4	Completed	Treatment	Adult Attention Deficit Hyperactivity Disorder (ADHD) With Co-occuring Anxiety and Depressive Disorders	1
4	Completed	Treatment	Attention Deficit Disorder (ADD) / Traumatic Brain Injury (TBI)	1
4	Completed	Treatment	Attention Deficit Disorder With Hyperactivity	1
4	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD)	7
4	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / Deficient Emotional Self-Regulation (DESR)	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	Recruiting	Other	Lisdexamfetamine	1
4	Recruiting	Treatment	Attention Deficit Disorder With Hyperactivity	1
4	Recruiting	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD)	1
4	Recruiting	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / Autism Spectrum Conditions/Disorders	1
4	Recruiting	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / Problem Behavior	1
4	Recruiting	Treatment	Attention Deficit/Hyperactivity Disorder	1
4	Recruiting	Treatment	Cognitive Impairments / RRSO	1
4	Terminated	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / BMI >30 kg/m2 / Glucose tolerance impaired	1
4	Terminated	Treatment	Depression, Bipolar	1
Not Available	Active Not Recruiting	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD)	3
Not Available	Completed	Not Available	Attention Deficit Disorder With Hyperactivity	1
Not Available	Completed	Not Available	Attention Deficit/Hyperactivity Disorder / Bipolar Disorder (BD)	1
Not Available	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD)	1
Not Available	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / Nicotine Dependence	1
Not Available	Completed	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD) / Sleep	1
Not Available	Not Yet Recruiting	Basic Science	Attention Deficit Disorder With Hyperactivity (ADHD)	1
Not Available	Recruiting	Not Available	Obesity, Morbid	1
Not Available	Recruiting	Treatment	Attention Deficit Disorder With Hyperactivity (ADHD)	1
Not Available	Withdrawn	Prevention	Planned RRSO	1
Not Available	Withdrawn	Treatment	Cognitive Impairments / RRSO	1

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

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)
Unlock Additional Data
US7659253	No	2010-02-09	2023-02-24
US7718619	No	2010-05-18	2023-02-24
US7659254	No	2010-02-09	2023-02-24
US7671030	No	2010-03-02	2023-02-24
US7662788	No	2010-02-16	2023-02-24
US7687467	No	2010-03-30	2023-02-24
US7678770	No	2010-03-16	2023-02-24
US7671031	No	2010-03-02	2023-02-24
US7713936	No	2010-05-11	2023-02-24
US7674774	No	2010-03-09	2023-02-24
US7678771	No	2010-03-16	2023-02-24
US7655630	No	2010-02-02	2023-02-24
US7687466	No	2010-03-30	2023-02-24
US7223735	No	2007-05-29	2023-02-24
US7700561	No	2010-04-20	2023-02-24
US7662787	No	2010-02-16	2023-02-24
US7723305	No	2010-05-25	2023-02-24
US7105486	No	2006-09-12	2023-02-24

Additional Data Available

Filed On

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

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Properties

State

Liquid

Experimental Properties

Property	Value	Source
water solubility	792 mg/mL (dimesylate salt)	FDA label
logP	-1.76	https://www.tga.gov.au/sites/.../auspar-lisdexamfetamine-dimesilate-131023-pi.docx
pKa	10.5	https://www.tga.gov.au/sites/.../auspar-lisdexamfetamine-dimesilate-131023-pi.docx

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	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

Details1. Trace amine-associated receptor 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Trace-amine receptor activity
Specific Function: Receptor for trace amines, including beta-phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amin...
Gene Name: TAAR1
Uniprot ID: Q96RJ0
Uniprot Name: Trace amine-associated receptor 1
Molecular Weight: 39091.34 Da

References

Miller GM: The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity. J Neurochem. 2011 Jan;116(2):164-76. doi: 10.1111/j.1471-4159.2010.07109.x. [PubMed:21073468]
Liu JF, Li JX: TAAR1 in Addiction: Looking Beyond the Tip of the Iceberg. Front Pharmacol. 2018 Mar 27;9:279. doi: 10.3389/fphar.2018.00279. eCollection 2018. [PubMed:29636691]
Pei Y, Asif-Malik A, Canales JJ: Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications. Front Neurosci. 2016 Apr 5;10:148. doi: 10.3389/fnins.2016.00148. eCollection 2016. [PubMed:27092049]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Hutson PH, Pennick M, Secker R: Preclinical pharmacokinetics, pharmacology and toxicology of lisdexamfetamine: a novel d-amphetamine pro-drug. Neuropharmacology. 2014 Dec;87:41-50. doi: 10.1016/j.neuropharm.2014.02.014. Epub 2014 Mar 1. [PubMed:24594478]
Tan-Kam T, Suthisisang C, Pavasuthipaisit C, Limsila P, Puangpetch A, Sukasem C: Importance of pharmacogenetics in the treatment of children with attention deficit hyperactive disorder: a case report. Pharmgenomics Pers Med. 2013;6:3-7. doi: 10.2147/PGPM.S36782. Epub 2013 Jan 11. [PubMed:23526481]
Vyvanse FDA label [File]

Transporters

Details1. Solute carrier family 15 member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Curator comments: These data are based on in vitro studies.

General Function: Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name: SLC15A1
Uniprot ID: P46059
Uniprot Name: Solute carrier family 15 member 1
Molecular Weight: 78805.265 Da

References

Pennick M: Absorption of lisdexamfetamine dimesylate and its enzymatic conversion to d-amphetamine. Neuropsychiatr Dis Treat. 2010 Jun 24;6:317-27. [PubMed:20628632]
Elvanse EPAR [File]

Drug created on May 14, 2007 19:24 / Updated on November 12, 2019 22:44

Lisdexamfetamine

Identification

Structure for Lisdexamfetamine (DB01255)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

Enzymes

References

Transporters

References