Identification

Name
Lisdexamfetamine
Accession Number
DB01255
Type
Small Molecule
Groups
Approved, Investigational
Description

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
Thumb
Synonyms
  • Lisdexamfetamine
Product Ingredients
IngredientUNIICASInChI Key
Lisdexamfetamine dimesylateSJT761GEGS608137-33-3CETWSOHVEGTIBR-FORAGAHYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VyvanseCapsule40 mg/1OralPhysicians Total Care, Inc.2009-03-20Not applicableUs
VyvanseCapsule10 mg/1OralShire LLC2014-08-30Not applicableUs
VyvanseCapsule70 mg/1OralShire LLC2007-02-23Not applicableUs
VyvanseTablet, chewable60 mg/1OralShire LLC2017-01-28Not applicableUs
VyvanseCapsule10 mgOralShire Pharma Canada Ulc2015-06-26Not applicableCanada
VyvanseCapsule10 mg/1OralAvera McKennan Hospital2015-03-262018-06-07Us
VyvanseCapsule50 mg/1OralShire LLC2007-02-23Not applicableUs
VyvanseTablet, chewable40 mg/1OralShire LLC2017-01-28Not applicableUs
VyvanseCapsule40 mgOralShire Pharma Canada Ulc2010-04-14Not applicableCanada
VyvanseCapsule70 mg/1OralPhysicians Total Care, Inc.2010-03-04Not applicableUs
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].

TargetActionsOrganism
UTrace amine-associated receptor 1
agonist
Humans
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].

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
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Lisdexamfetamine is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe therapeutic efficacy of 1-benzylimidazole can be decreased when used in combination with Lisdexamfetamine.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Lisdexamfetamine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Lisdexamfetamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Lisdexamfetamine is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Lisdexamfetamine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when Lisdexamfetamine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Lisdexamfetamine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with 6-O-benzylguanine.
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
  1. Jasinski DR, Krishnan S: Human pharmacology of intravenous lisdexamfetamine dimesylate: abuse liability in adult stimulant abusers. J Psychopharmacol. 2009 Jun;23(4):410-8. doi: 10.1177/0269881108093841. Epub 2008 Jul 17. [PubMed:18635707]
  2. Madaan V: Lisdexamfetamine dimesylate for childhood ADHD. Drugs Today (Barc). 2008 May;44(5):319-24. doi: 10.1358/dot.2008.44.5.1215724. [PubMed:18548134]
  3. Krishnan S, Moncrief S: An evaluation of the cytochrome p450 inhibition potential of lisdexamfetamine in human liver microsomes. Drug Metab Dispos. 2007 Jan;35(1):180-4. Epub 2006 Oct 11. [PubMed:17035599]
  4. Goodman DW: Lisdexamfetamine dimesylate (vyvanse), a prodrug stimulant for attention-deficit/hyperactivity disorder. P T. 2010 May;35(5):273-87. [PubMed:20514273]
  5. Miller GM: The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity. J Neurochem. 2011 Jan;116(2):164-76. doi: 10.1111/j.1471-4159.2010.07109.x. [PubMed:21073468]
  6. Liu JF, Li JX: TAAR1 in Addiction: Looking Beyond the Tip of the Iceberg. Front Pharmacol. 2018 Mar 27;9:279. doi: 10.3389/fphar.2018.00279. eCollection 2018. [PubMed:29636691]
  7. Pei Y, Asif-Malik A, Canales JJ: Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications. Front Neurosci. 2016 Apr 5;10:148. doi: 10.3389/fnins.2016.00148. eCollection 2016. [PubMed:27092049]
  8. Vyvanse, Canadian Monograph [File]
  9. EPAR: Lisdexamfetamine dimesylate [File]
  10. WHO Summary: Lisdexamfetamine [File]
External Links
Human Metabolome Database
HMDB0015385
PubChem Compound
11597698
PubChem Substance
46505358
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
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentMethamphetamine Dependence1
1CompletedNot AvailableAttention Deficit Disorder With Hyperactivity (ADHD)1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableSchizophrenic Disorders1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentDrug Users / Healthy Volunteers1
1CompletedTreatmentHealthy Volunteers1
1TerminatedNot AvailableHealthy Volunteers1
1, 2CompletedBasic ScienceAttention Deficit Disorder With Hyperactivity (ADHD)1
1, 2CompletedTreatmentAmphetamine-Related Disorders / Attention Deficit Disorder With Hyperactivity / Substance-Related Disorders1
1, 2CompletedTreatmentDependence, Cocaine2
2CompletedNot AvailableSleep Deprivation1
2CompletedTreatmentAmphetamine-Related Disorders / Attention Deficit Disorder With Hyperactivity / Substance-Related Disorders1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Deficient Emotional Self-Regulation (DESR)1
2CompletedTreatmentBinge Eating Disorder (BED)1
2CompletedTreatmentDependence, Cocaine1
2CompletedTreatmentDisseminated Sclerosis1
2CompletedTreatmentMajor Depressive Disorder (MDD)3
2CompletedTreatmentSchizophrenia and Predominant Negative Symptoms1
2CompletedTreatmentSevere Mood Dysregulation1
2RecruitingNot AvailableBinge Eating Disorder (BED)1
2RecruitingTreatmentAttention Deficit Disorder (ADD) / Attention Deficit Disorder With Hyperactivity (ADHD)1
2RecruitingTreatmentBulimia Nervosa (BN)1
3Active Not RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Attention-Deficit/Hyperactivity Disorder1
3CompletedNot AvailableAttention Deficit Disorder With Hyperactivity (ADHD)1
3CompletedTreatmentAttention Deficit Disorder (ADD) / Traumatic Brain Injury (TBI)1
3CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)8
3CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Attention Deficit Disorders With Hyperactivity1
3CompletedTreatmentAttention-Deficit/Hyperactivity Disorder1
3CompletedTreatmentBinge Eating Disorder (BED)5
3CompletedTreatmentMajor Depressive Disorder (MDD)2
3TerminatedTreatmentBipolar / Depression1
3TerminatedTreatmentDepression, Bipolar1
3TerminatedTreatmentMajor Depressive Disorder (MDD)1
4CompletedNot AvailableAttention Deficit Disorder With Hyperactivity (ADHD)2
4CompletedBasic ScienceAttention Deficit Disorder With Hyperactivity (ADHD)2
4CompletedBasic ScienceAttention Deficit/Hyperactivity Disorder1
4CompletedTreatmentADHD Specifically With Executive Function Impairment1
4CompletedTreatmentAdult Attention Deficit Hyperactivity Disorder (ADHD) With Co-occuring Anxiety and Depressive Disorders1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)7
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Deficient Emotional Self-Regulation (DESR)1
4CompletedTreatmentAttention-Deficit/Hyperactivity Disorder4
4CompletedTreatmentBrain Activity / Cognition / Menopause1
4CompletedTreatmentCognitive Impairments / Myalgic Encephalomyelitis (ME)1
4CompletedTreatmentCognitive Impairments / Symptomatic Menopause1
4CompletedTreatmentMajor Depressive Disorder (MDD)1
4RecruitingOtherLisdexamfetamine1
4RecruitingTreatmentAttention Deficit Disorder (ADD) / Traumatic Brain Injury (TBI)1
4RecruitingTreatmentAttention Deficit Disorder With Hyperactivity1
4RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
4RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Autism Spectrum Conditions/Disorders1
4RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Problem Behavior1
4RecruitingTreatmentCognitive Impairments / RRSO1
4TerminatedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / BMI >30 kg/m2 / Glucose tolerance impaired1
4TerminatedTreatmentDepression, Bipolar1
Not AvailableActive Not RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)3
Not AvailableCompletedNot AvailableAttention Deficit/Hyperactivity Disorder / Bipolar Disorder (BD)1
Not AvailableCompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
Not AvailableCompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Nicotine Dependence1
Not AvailableCompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Sleep1
Not AvailableNot Yet RecruitingBasic ScienceAttention Deficit Disorder With Hyperactivity (ADHD)1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
Not AvailableWithdrawnPreventionPlanned RRSO1
Not AvailableWithdrawnTreatmentCognitive Impairments / RRSO1

Pharmacoeconomics

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

Properties

State
Liquid
Experimental Properties
PropertyValueSource
water solubility792 mg/mL (dimesylate salt)FDA label
logP-1.76https://www.tga.gov.au/sites/.../auspar-lisdexamfetamine-dimesilate-131023-pi.docx
pKa10.5https://www.tga.gov.au/sites/.../auspar-lisdexamfetamine-dimesilate-131023-pi.docx
Predicted Properties
PropertyValueSource
Water Solubility0.0877 mg/mLALOGPS
logP1.01ALOGPS
logP1.14ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)15.89ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81.14 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.31 m3·mol-1ChemAxon
Polarizability31.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9858
Blood Brain Barrier+0.9444
Caco-2 permeable+0.664
P-glycoprotein substrateSubstrate0.6919
P-glycoprotein inhibitor INon-inhibitor0.9264
P-glycoprotein inhibitor IINon-inhibitor0.9802
Renal organic cation transporterNon-inhibitor0.8398
CYP450 2C9 substrateNon-substrate0.8303
CYP450 2D6 substrateNon-substrate0.621
CYP450 3A4 substrateNon-substrate0.7228
CYP450 1A2 substrateNon-inhibitor0.7025
CYP450 2C9 inhibitorNon-inhibitor0.9337
CYP450 2D6 inhibitorNon-inhibitor0.858
CYP450 2C19 inhibitorNon-inhibitor0.7568
CYP450 3A4 inhibitorNon-inhibitor0.5499
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8494
Ames testNon AMES toxic0.7156
CarcinogenicityNon-carcinogens0.854
BiodegradationNot ready biodegradable0.8575
Rat acute toxicity2.0058 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9688
hERG inhibition (predictor II)Non-inhibitor0.9004
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

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

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

Enzymes

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

Transporters

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

Drug created on May 14, 2007 19:24 / Updated on February 13, 2019 05:18