Lisdexamfetamine
- Lisdexamfetamine
- 608137-32-2
- lisdexamphetamine
- Lisdexamfetamine [INN]
- UNII-H645GUL8KJ
- Create:2006-10-26
- Modify:2024-12-28
- Dimesylate, Lis-dexamfetamine
- Dimesylate, Lisdexamfetamine
- elvanse
- Lis dexamfetamine Dimesylate
- lis-dexamfetamine dimesylate
- lisdexamfetamine
- lisdexamfetamine dimesylate
- NRP 104
- NRP-104
- NRP104
- Vyvanse
- Lisdexamfetamine
- 608137-32-2
- lisdexamphetamine
- Lisdexamfetamine [INN]
- UNII-H645GUL8KJ
- H645GUL8KJ
- L-lysine-d-amphetamine
- NRP104
- L-lysine-dextroamphetamine
- HSDB 8277
- Lisdexamfetamine (INN)
- (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide
- (2S)-2,6-Diamino-N-((1S)-1-methyl-2-phenylethyl)hexanamide
- DTXSID00209652
- N-((1S)-1-METHYL-2-PHENYLETHYL)-L-LYSINAMIDE
- Dimesylate, Lis-dexamfetamine
- (2S, 2'S)-2,6-DIAMINO-N-(1-PHENYLPROPAN-2-YL)HEXANAMIDE
- HEXANAMIDE, 2,6-DIAMINO-N-((1S)-1-METHYL-2-PHENYLETHYL)-, (2S)-
- (2S)-2,6-diamino-N-((2S)-1-phenylpropan-2-yl)hexanamide
- lisdexanfetamina
- lisdexamfetaminum
- LISDEXAMFETAMINE [MI]
- SCHEMBL158949
- GTPL7213
- LISDEXAMFETAMINE [VANDF]
- CHEMBL1201222
- DTXCID50132143
- LISDEXAMFETAMINE [WHO-DD]
- N06BA12
- CHEBI:135925
- DB01255
- NS00017968
- D08130
- Q6558704
- (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanimidic acid
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
H301: Toxic if swallowed [Danger Acute toxicity, oral]
H311: Toxic in contact with skin [Danger Acute toxicity, dermal]
H331: Toxic if inhaled [Danger Acute toxicity, inhalation]
H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]
P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P308+P316, P316, P321, P330, P361+P364, P370+P378, P403+P233, P403+P235, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)
M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007
M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
◉ Summary of Use during Lactation
Lisdexamfetamine is a prodrug of dextroamphetamine. In dosages prescribed for medical indications, some evidence indicates that dextroamphetamine might not affect nursing infants adversely. The effect of dextroamphetamine in milk on the neurological development of the infant has not been well studied. It is possible that large dosages of dextroamphetamine might interfere with milk production, especially in women whose lactation is not well established. Therapeutic dosages of amphetamine can be used during nursing with monitoring of the infant for irritability, insomnia, and feeding difficulty. Breastfeeding is generally discouraged in mothers who are actively abusing amphetamines.
◉ Effects in Breastfed Infants
The author of a 1973 newsletter reported a personal communication from the drug manufacturer which stated that of 103 nursing mothers treated with dextroamphetamine (dosage unspecified) for postpartum depression, no infant showed any evidence of stimulation or insomnia.
Four mothers averaging 5.5 months postpartum (range 3.3 to 10 months) were taking dextroamphetamine in an average dosage of 18 mg daily (range 15 to 45 mg daily in 2 to 4 divided doses) for attention deficit hyperactivity disorder. Their infants had been breastfed (extent not stated) since birth. The infants all had weights between the 10th and 75th percentiles for their age, normal progress, and no adverse effects according to their pediatricians. Denver developmental ages for 2 of the infants were 100% and 117% of normal.
In a prospective study, lactating women taking either lisdexamfetamine (Vyvanse®, Shire; n = 6) or mixed racemic amphetamine salts (n = 7) for attention deficit hyperactivity disorder were followed by telephone for several months to 5 years. Seven had also taken one of the drugs during pregnancy. At an average age of follow-up of 18 months, 5 of their 13 infants (5 fully breastfed) had experienced an adverse reaction possibly related to amphetamine in milk; 1 infant had somnolence, 3 had crying or restlessness, and 4 had colic or constipation. Four of these 5 were only partially breastfed from birth onward. All infants had normal Denver developmental scale and pediatric quality of life scores. The authors concluded that therapeutic used of amphetamines is likely compatible with breastfeeding.
◉ Effects on Lactation and Breastmilk
In 2 papers by the same authors, 20 women with normal physiologic hyperprolactinemia were studied on days 2 or 3 postpartum. Eight received dextroamphetamine 7.5 mg intravenously, 6 received 15 mg intravenously and 6 who served as controls received intravenous saline. The 7.5 mg dose reduced serum prolactin by 25 to 32% compared to control, but the difference was not statistically significant. The 15 mg dose significantly decreased serum prolactin by 30 to 37% at times after the infusion. No assessment of milk production was presented. The authors also quoted data from another study showing that a 20 mg oral dose of dextroamphetamine produced a sustained suppression of serum prolactin by 40% in postpartum women. The maternal prolactin level in a mother with established lactation may not affect her ability to breastfeed.
In a retrospective Australian study, mothers who used intravenous amphetamines during pregnancy were less likely to be breastfeeding their newborn infants at discharge than mothers who abused other drugs (27% vs 42%). The cause of this difference was not determined.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=VOBHXZCDAVEXEY-JSGCOSHPSA-N
- Avoid antacids. Urinary excretion of lisdexamfetamine is elevated when the urine is more acidic. Antacids like sodium bicarbonate alkalinize the urine; therefore, they may reduce lisdexamfetamine elimination.
- Limit foods and supplements high in vitamin C. Urinary excretion of lisdexamfetamine is elevated when the urine is more acidic. Vitamin C acidifies the urine and, therefore, may increase lisdexamfetamine elimination.
- Take with or without food. Food prolongs Tmax by approximately one hour, but does not significantly affect drug exposure.
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/Lisdexamfetaminehttps://commonchemistry.cas.org/detail?cas_rn=608137-32-2
- ChemIDplusLisdexamfetamine [INN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0608137322ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useLisdexamfetaminehttps://www.drugbank.ca/drugs/DB01255
- EPA DSSToxLisdexamfetaminehttps://comptox.epa.gov/dashboard/DTXSID00209652CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingLISDEXAMFETAMINEhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/H645GUL8KJ
- Hazardous Substances Data Bank (HSDB)Lisdexamfetaminehttps://pubchem.ncbi.nlm.nih.gov/source/hsdb/8277
- Human Metabolome Database (HMDB)LICENSEHMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.http://www.hmdb.ca/citingLisdexamfetaminehttp://www.hmdb.ca/metabolites/HMDB0015385
- ChEBILisdexamfetaminehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:135925
- FDA Pharm ClassesLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingLISDEXAMFETAMINEhttps://dailymed.nlm.nih.gov/dailymed/browse-drug-classes.cfmFDA Pharmacological Classificationhttps://www.fda.gov/ForIndustry/DataStandards/StructuredProductLabeling/ucm162549.htm
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- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licenceLISDEXAMFETAMINEhttps://platform.opentargets.org/drug/CHEMBL1201222
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- DailyMed
- Drug Induced Liver Injury Rank (DILIrank) DatasetLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- Therapeutic Target Database (TTD)Lisdexamfetaminehttps://idrblab.net/ttd/data/drug/details/D00DEF
- Drugs and Lactation Database (LactMed)Lisdexamfetaminehttps://www.ncbi.nlm.nih.gov/books/n/lactmed/LM834/
- EPA Chemical and Products Database (CPDat)EPA CPDat Classificationhttps://www.epa.gov/chemical-research/chemical-and-products-database-cpdat
- EU Clinical Trials Register
- National Drug Code (NDC) DirectoryLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlAnatomical Therapeutic Chemical (ATC) classificationhttp://www.genome.jp/kegg-bin/get_htext?br08303.kegTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.keg
- Metabolomics Workbench
- NLM RxNorm TerminologyLICENSEThe RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.htmllisdexamfetaminehttps://rxnav.nlm.nih.gov/id/rxnorm/700810
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/LISDEXAMFETAMINENORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/aboutlisdexamfetaminehttps://pharos.nih.gov/ligands/D59LKVNCMD2M
- SpectraBaseLisdexamfetaminehttps://spectrabase.com/spectrum/7KjnqvoLAd0Lisdexamphetaminehttps://spectrabase.com/spectrum/JFe43hwCQSm
- Springer Nature
- WHO Anatomical Therapeutic Chemical (ATC) ClassificationLICENSEUse of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.https://www.whocc.no/copyright_disclaimer/Lisdexamfetaminehttps://www.whocc.no/atc_ddd_index/?code=N06BA12
- Wikidatalisdexamfetaminehttps://www.wikidata.org/wiki/Q6558704
- Wikipedia1,2,4-Trichlorobenzenehttps://en.wikipedia.org/wiki/1,2,4-TrichlorobenzeneLisdexamfetaminehttps://en.wikipedia.org/wiki/Lisdexamfetamine
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlLisdexamfetamine Dimesylatehttps://www.ncbi.nlm.nih.gov/mesh/2010014Central Nervous System Stimulantshttps://www.ncbi.nlm.nih.gov/mesh/68000697Dopamine Uptake Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68018765
- PubChem
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 402479794https://pubchem.ncbi.nlm.nih.gov/substance/402479794
- NCBI