LISDEXAMFETAMINE DIMESYLATE

First marketed in 1937

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H25N3O.2CH4O3S
Molecular Weight	455.59
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LISDEXAMFETAMINE DIMESYLATE

Structure Search

SMILES

CS(O)(=O)=O.CS(O)(=O)=O.C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN

InChI

InChIKey=CETWSOHVEGTIBR-FORAGAHYSA-N

InChI=1S/C15H25N3O.2CH4O3S/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16;2*1-5(2,3)4/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19);2*1H3,(H,2,3,4)/t12-,14-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C15H25N3O
Molecular Weight	263.3785
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017078s048lbl.pdf
Curator's Comment: description was created based on several sources, including https://blackpoppymag.wordpress.com/substances/dexedrine-dexamphetamine/

Amphetamine is also prescribed in enantiopure and prodrug form as dextroamphetamine and lisdexamfetamine respectively. Lisdexamfetamine is structurally different from amphetamine, and is inactive until it metabolizes into dextroamphetamine. Dextroamphetamine is useful for those with ADHD and Narcolepsy. It improves self-control for people who have a hard time naturally controlling themselves. Dextroamphetamine aids a person learning and memory of words, and perhaps makes the brain stronger. When a person given dextroamphetamine is tested, their brain is extremely active in the brain parts required for the test and radically less active in other parts. Short practice sessions with dextroamphetamine have a greater effect on learning than sessions without dextroamphetamine. Dextroamphetamine raises decision-making scores, improves choices, and changes beliefs about rewards; at the same time, dextroamphetamine barely—if at all—affects guesses of time. Those who feel lower amounts of joy from dextroamphetamine have greater impulsivity improvements compared to those who feel extreme happiness. The drug should be avoided for those who have hypersensitivity to amphetamines, a history of drug abuse, cardiovascular diseases, hypertensive disease, hyperthyroidism, or in those with glaucoma. In 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dextroamphetamine, and in 1937 Smith, Kline, and French introduced Dexedrine tablets, under the tradename Dexedrine. In the United States, Dexedrine tablets were approved to treat narcolepsy, attention disorders, depression, and obesity. Dexedrine, along with other sympathomimetic, was eventually classified as schedule II, the most restrictive category possible for a drug with recognized medical uses. The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). Modulation of serotonergic pathways may contribute to the calming effect.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
catecholamine secretion 14 Target ID: GO:0050432 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021977lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/28376679	Modulator 828
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17239355	Modulator 828
Synaptic vesicular amine transporter 57 Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7751968	Inhibitor 8297
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19244097	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Attention deficit hyperactivity disorder 68 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf	Primary	Approved 8429	VYVANSE Approved Use VYVANSE® is indicated for the treatment of: Attention Deficit Hyperactivity Disorder (ADHD) [see Clinical Studies (14.1) Launch Date 2007
Moderate to severe binge eating disorder 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf	Primary	Approved 8429	VYVANSE Approved Use VYVANSE® is indicated for the treatment of: Attention Deficit Hyperactivity Disorder (ADHD) [see Clinical Studies (14.1) Launch Date 2007
Attention deficit hyperactivity disorder 68 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017078s048lbl.pdf	Primary	Approved 8429	DEXEDRINE Approved Use Narcolepsy. Attention Deficit Disorder with Hyperactivity. As an integral part of a total treatment program that typically includes other measures (psychological, educational, social) for patients (ages 6 years to 16 years) with this syndrome. A diagnosis of Attention Deficit Hyperactivity Disorder (ADHD; DSM-IV) implies the presence of the hyperactive-impulsive or inattentive symptoms that caused impairment and were present before age 7 years. The symptoms must cause clinically significant impairment, e.g., in social, academic, or occupational functioning, and be present in 2 or more settings, e.g., school (or work) and at home. The symptoms must not be better accounted for by another mental disorder. For the Inattentive Type, at least 6 of the following symptoms must have persisted for at least 6 months: lack of attention to details/careless mistakes; lack of sustained attention; poor listener; failure to follow through on tasks; poor organization; avoids tasks requiring sustained mental effort; loses things; easily distracted; forgetful. For the Hyperactive-Impulsive Type, at least 6 of the following symptoms must have persisted for at least 6 months: fidgeting/squirming; leaving seat; inappropriate running/climbing; difficulty with quiet activities; “on the go”; excessive talking; blurting answers; can't wait turn; intrusive. The Combined Type requires both inattentive and hyperactive-impulsive criteria to be met. Launch Date 1980

C_max

Value	Dose	Analyte	Population
47.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18021493/	70 mg 1 times / day multiple, oral dose: 70 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LISDEXAMFETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
24.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
36.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/040361Orig1s017lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
60.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18021493/	70 mg 1 times / day multiple, oral dose: 70 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LISDEXAMFETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
431 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18021493/	70 mg 1 times / day multiple, oral dose: 70 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LISDEXAMFETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/040361Orig1s017lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
70 mg 1 times / day multiple, oral (max) Recommended Dose: 70 mg, 1 times / day Route: oral Route: multiple Dose: 70 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	unhealthy, 13 - 17 n = 233 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorder Age Group: 13 - 17 Sex: M+F Population Size: 233 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	Disc. AE: Irritability, Decreased appetite... AEs leading to discontinuation/dose reduction: Irritability (1.3%) Decreased appetite (0.86%) Insomnia (0.86%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8
1200 mg single, oral Overdose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/30730334 Page: e771	healthy, 17 n = 1 Health Status: healthy Age Group: 17 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30730334 Page: e771	Disc. AE: Delirium, Tachycardia... AEs leading to discontinuation/dose reduction: Delirium (acute) Tachycardia Hypertension Tachypnea Creatine kinase increased (mild) Sources: https://pubmed.ncbi.nlm.nih.gov/30730334 Page: e771
70 mg 1 times / day multiple, oral (max) Recommended Dose: 70 mg, 1 times / day Route: oral Route: multiple Dose: 70 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	unhealthy, 18 - 55 n = 358 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorder Age Group: 18 - 55 Sex: M+F Population Size: 358 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	Disc. AE: Insomnia, Tachycardia... AEs leading to discontinuation/dose reduction: Insomnia (2%) Tachycardia (1%) Irritability (1%) Hypertension (1%) Headache (1%) Anxiety (1%) Dyspnea (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8
70 mg 1 times / day multiple, oral (max) Recommended Dose: 70 mg, 1 times / day Route: oral Route: multiple Dose: 70 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	unhealthy, 6 - 12 n = 218 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorder Age Group: 6 - 12 Sex: M+F Population Size: 218 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	Disc. AE: Ventricular hypertrophy, Tic... AEs leading to discontinuation/dose reduction: Ventricular hypertrophy (1%) Tic (1%) Vomiting (1%) Psychomotor hyperactivity (1%) Insomnia (1%) Rash (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8
30 mg 1 times / day steady, oral Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00735371	unhealthy, adolescents n = 78 Health Status: unhealthy Condition: Attention-Deficit/Hyperactivity Disorder Age Group: adolescents Population Size: 78 Sources: https://clinicaltrials.gov/ct2/show/NCT00735371	Other AEs: Decreased appetite, Insomnia... Other AEs: Decreased appetite (below serious, 29 patients) Insomnia (below serious, 7 patients) Weight decreased (below serious, 3 patients) Irritability (below serious, 6 patients) Fatigue (below serious, 4 patients) Nasopharyngitis (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00735371
20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	healthy, adult n = 27 Health Status: healthy Condition: Acute Sleep Loss Age Group: adult Sex: M Population Size: 27 Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	Other AEs: Nausea... Other AEs: Nausea (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT01096680
50 mg single, oral Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	healthy, adult n = 27 Health Status: healthy Condition: Acute Sleep Loss Age Group: adult Sex: M Population Size: 27 Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	Other AEs: Headache, Nausea... Other AEs: Headache (below serious, 4 patients) Nausea (below serious, 1 patient) Vomiting (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01096680
70 mg single, oral Dose: 70 mg Route: oral Route: single Dose: 70 mg Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	healthy, adult n = 27 Health Status: healthy Condition: Acute Sleep Loss Age Group: adult Sex: M Population Size: 27 Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	Other AEs: Headache, Nausea... Other AEs: Headache (below serious, 2 patients) Nausea (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01096680
70 mg 1 times / day steady, oral (max) Dose: 70 mg, 1 times / day Route: oral Route: steady Dose: 70 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01101022	unhealthy, adult n = 79 Health Status: unhealthy Condition: Attention-Deficit/Hyperactivity Disorder Age Group: adult Population Size: 79 Sources: https://clinicaltrials.gov/ct2/show/NCT01101022	Other AEs: Diarrhea, Dry mouth... Other AEs: Diarrhea (below serious, 6 patients) Dry mouth (below serious, 25 patients) Fatigue (below serious, 6 patients) Feeling jittery (below serious, 10 patients) Irritability (below serious, 8 patients) Upper respiratory tract infection (below serious, 5 patients) Heart rate increased (below serious, 4 patients) Weight decreased (below serious, 8 patients) Anorexia (below serious, 4 patients) Decreased appetite (below serious, 26 patients) Headache (below serious, 20 patients) Initial insomnia (below serious, 8 patients) Insomnia (below serious, 10 patients) Libido decreased (below serious, 4 patients) Hyperhidrosis (below serious, 5 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01101022
70 mg 1 times / day multiple, oral Recommended Dose: 70 mg, 1 times / day Route: oral Route: multiple Dose: 70 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorder\|Binge Eating Disorder Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.1	Disc. AE: Abuse, Dependence... AEs leading to discontinuation/dose reduction: Abuse Dependence Cardiovascular disorder (NOS) (grade 3-5) Stroke (serious) Myocardial infarction (serious) Blood pressure increased Heart rate increased Psychiatric symptom NOS Psychotic symptom Manic symptom Growth suppression Vascular disorders Raynaud's phenomenon Serotonin syndrome Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.1
50 mg 1 times / day steady, oral (max) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01148979	unhealthy n = 28 Health Status: unhealthy Condition: Major Depressive Disorder Population Size: 28 Sources: https://clinicaltrials.gov/ct2/show/NCT01148979	Other AEs: Decreased appetite, Dry mouth... Other AEs: Decreased appetite (below serious, 8 patients) Dry mouth (below serious, 7 patients) Insomnia (below serious, 10 patients) Irritability (below serious, 3 patients) Diaphoresis (below serious, 2 patients) Libido decreased (below serious, 2 patients) Tinnitus (below serious, 2 patients) Muscle tension (below serious, 4 patients) Tachycardia (below serious, 3 patients) Paresthesia (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01148979

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852 substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2B6 810 CYP2C19 1478	CYP 270

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4	likely
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 87.3 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 89 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 90 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 90.8 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 92.1 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 92.5 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 94.2 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4 Page: 4.0	likely		likely (co-administration study) Comment: Amphetamines and amphetamine derivatives are known to be metabolized, to some degree, by cytochrome P450 2D6 (CYP2D6) and display minor inhibition of CYP2D6 metabolism; concomitant use of DEXEDRINE and CYP2D6 inhibitors may increase the exposure of DEXEDRINE; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4 Page: 4.0
CYP 270	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021977s034,208510s002lbl.pdf Page: 21.0	no

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00E9T8
AA Blocks	AA00DRV1	https://www.aablocks.com/goods/Goods/detail?id=AA00DRV1
Alfa Chemistry	ACM608137333
Angene	AGN-PC-0WH4QC
Aurora Fine Chemicals LLC	A17.876.402	http://online.aurorafinechemicals.com/info?ID=A17.876.402
Aurora Fine Chemicals LLC	K16.670.581	http://online.aurorafinechemicals.com/info?ID=K16.670.581
Avantor Inc	101096-690	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-690
Avantor Inc	75835-260	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
BioCrick	BCC5942	http://www.biocrick.com/D-Amphetamine-sulfate-BCC5942.html
Cayman Chemical	18050
ChemMol	44007218	http://www.chemmol.com/chemmol/44007218.html
Compound Cloud	11597697
Compound Cloud	11597698
LGC Standards	LGCFOR1359.00	https://www.lgcstandards.com/US/en/p/LGCFOR1359.00
LGC Standards	MM1359.00	https://www.lgcstandards.com/US/en/p/MM1359.00
MolPort	MolPort-046-693-343
Parchem	16880	http://www.parchem.com/chemical-supplier-distributor/DITAB-006880.aspx
Sigma Aldrich	L-026
Sigma Aldrich	L-026\|CERILLIAN
Sigma-Aldrich	A3278_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/a3278?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A5880_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a5880?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1180004_USP	https://www.sigmaaldrich.com/catalog/product/usp/1180004?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S525797	http://www.smolecule.com/products/s525797
THE BioTek	bt-267390	https://www.thebiotek.com/product/inhibitors/bt-267390
THE BioTek	bt-386638	https://www.thebiotek.com/product/others/bt-386638
Tocris	2813	https://www.tocris.com/products/d-amphetamine-sulfate_2813
Toronto Research Chemicals	KIT2550
Toronto Research Chemicals	L468880
Toronto Research Chemicals	L468885
ZINC	ZINC000011680943	http://zinc15.docking.org/substances/ZINC000011680943
iChemical	EBD10545	http://www.ichemical.com/chemicals/cas-608137-33-3
iChemical	EBD2638102	http://www.ichemical.com/products/51-63-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-1818516035
mcule	MCULE-7002483605

PubMed

Title	Date	PubMed
Lithium prevention of amphetamine-induced 'manic' excitement and of reserpine-induced 'depression' in mice: possible role of 2-phenylethylamine.	1978 Dec 8	104329
Changes in striatal D2-receptor density following chronic treatment with amphetamine as assessed with PET in nonhuman primates.	1999 Feb	10024013
Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons.	1999 Jun	10336889
Using amphetamine isomer ratios to determine the compliance of amphetamine abusers prescribed dexedrine.	2000 Apr	10774542
Neuronal degeneration in the limbic system of weanling rats exposed to saline, hyperthermia or d-amphetamine.	2000 Dec 8	11102570
Dopaminergic mRNA expression in the intact substantia nigra of unilaterally 6-OHDA-lesioned and grafted rats: an in situ hybridization study.	2001	11314769
Effects of systemic injections of dopaminergic agents on the habituation of rats submitted to an open field test.	2001	11174051
Interleukin-2 potentiates novelty- and GBR 12909-induced exploratory activity.	2001 Apr 27	11311862
Tyrosine improves behavioral and neurochemical deficits caused by cold exposure.	2001 Feb	11274672
Differences in locomotor response to an inescapable novel environment predict sensitivity to aversive effects of amphetamine.	2001 Feb	11270513
Transcranial magnetic stimulation in an amphetamine hyperactivity model of mania.	2001 Feb	11256461
Conditioned activity to amphetamine in transgenic mice expressing an antisense RNA against the glucocorticoid receptor.	2001 Feb	11256444
Relevance of pharmacokinetic parameters in animal models of methamphetamine abuse.	2001 Feb	11180503
Regional distribution of methamphetamine in autopsied brain of chronic human methamphetamine users.	2001 Feb 15	11182268
Neuroprotective effect of vitamin E on the early model of Parkinson's disease in rat: behavioral and histochemical evidence.	2001 Feb 16	11172767
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry.	2001 Feb 25	11236083
Selective inhibition of amine oxidases differently potentiate the hypophagic effect of benzylamine in mice.	2001 Feb 9	11173067
Acute hydrocortisone administration does not affect subjective responses to d-amphetamine in humans.	2001 Jan	11271411
What is a "low dose" of d-amphetamine for inducing behavioral effects in laboratory rats?	2001 Jan 1	11205415
Amphetamine-induced dopamine release in human ventral striatum correlates with euphoria.	2001 Jan 15	11164755
Cannabinoid CB1 receptor knockout mice fail to self-administer morphine but not other drugs of abuse.	2001 Jan 8	11163634
Differential sensitivity to NaCl for inhibitors and substrates that recognize mutually exclusive binding sites on the neuronal transporter of dopamine in rat striatal membranes.	2001 Mar	11248372
Previous exposure to amphetamine enhances the subsequent locomotor response to a D1 dopamine receptor agonist when glutamate reuptake is inhibited.	2001 Mar 1	11222671
Addition of a 5-HT receptor agonist to methylphenidate potentiates the reduction of [123I]FP-CIT binding to dopamine transporters in rat frontal cortex and hippocampus.	2001 Mar 1	11169768
Dissociations between the effects of intra-accumbens administration of amphetamine and exposure to a novel environment on accumbens dopamine and cortical acetylcholine release.	2001 Mar 16	11251215
Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene.	2001 May 1	11312315
Poison centers detect an unexpectedly frequent number of adverse drug reactions to lisdexamfetamine.	2008 Jul	18594051
Alopecia following initiation of lisdexamfetamine in a pediatric patient.	2009	20098534
Lisdexamfetamine dimesylate: in attention-deficit hyperactivity disorder in adults.	2009	19453202
Lisdexamfetamine for treatment of attention-deficit/hyperactivity disorder.	2009 Apr	19318601
Case histories in pharmaceutical risk management.	2009 Dec 1	19767156
An update on central nervous system stimulant formulations in children and adolescents with attention-deficit/hyperactivity disorder.	2009 Jun	19470858
Advances in the treatment of attention-deficit/hyperactivity disorder: a guide for pediatric neurologists.	2010 Dec	21183129
Focus on Lisdexamfetamine: A Review of its use in Child and Adolescent Psychiatry.	2010 Nov	21037922

Patents

Sample Use Guides

In Vivo Use Guide

Attention-deficit/hyperactivity disorder: Initial: 30 mg once daily in the morning; may increase in increments of 10 mg or 20 mg at weekly intervals until optimal response is obtained; maximum: 70 mg/day. Binge eating disorder: Initial: 30 mg once daily in the morning; may titrate in increments of 20 mg at weekly intervals to target dose of 50 to 70 mg once daily (maximum: 70 mg/day).

Route of Administration: Oral

In Vitro Use Guide

Incubation of lisdexamfetamine in microsomal suspensions at concentrations ranging from 0.01 to 100 M showed no concentration-dependent inhibition for any of the isoenzymes under investigation (CYP1A2, CYP2A6, CYP2B6, CYP2C9, CYP2C19, CYP2D6, CYP3A, CYP3A4).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:52:55 GMT 2023` Edited by `admin` on `Fri Dec 15 15:52:55 GMT 2023`
Record UNII	SJT761GEGS
Record Status	`Validated (UNII)`
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Name

Type

Language

LISDEXAMFETAMINE DIMESYLATE

Official Name

English

NRP104

Code

English

(2S)-2,6-DIAMINO-N-((1S)-1-METHYL-2-PHENYLETHYL)HEXANAMIDE DIMETHANESULPHONATE

Systematic Name

English

VYVANSE

Brand Name

English

Lisdexamfetamine Mesilate [WHO-DD]

Common Name

English

HEXANAMIDE, 2,6-DIAMINO-N-((1S)-1-METHYL-2-PHENYLETHYL), (2S), DIMETHANESULPHONATE

Common Name

English

SPD-489

Code

English

LISDEXAMFETAMINE DIMESYLATE [USAN]

Common Name

English

HEXANAMIDE, 2,6-DIAMINO-N-((1S)-1-METHYL-2-PHENYLETHYL), (2S), DIMETHANESULFONATE

Common Name

English

LISDEXAMFETAMINE DIMETHANESULFONATE [MI]

Common Name

English

LISDEXAMFETAMINE DIMESYLATE [ORANGE BOOK]

Common Name

English

LISDEXAMFETAMINE MESILATE [MART.]

Common Name

English

LISDEXAMFETAMINE DIMESYLATE [VANDF]

Common Name

English

TYVENSE

Brand Name

English

SPD489

Code

English

LISDEXAMFETAMINE MESILATE

Common Name

English

LISDEXAMFETAMINE DIMETHANESULFONATE

Common Name

English

LISDEXAMFETAMINE MESILATE [JAN]

Common Name

English

(2S)-2,6-Diamino-N-[(1S)-1-methyl-2-phenylethyl]hexanamide dimethanesulfonate

Systematic Name

English

NRP-104

Code

English

LISDEXAMPHETAMINE DIMESILATE

Common Name

English

LISDEXAMFETAMINE DIMESILATE

Common Name

English

Classification Tree Code System Code

DEA NO.

1205