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Latest revision as of 08:36, 3 October 2024 edit undoEntranced98 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers173,901 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper |
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{{Short description|Chemical compound}} |
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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{chembox |
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{{Infobox drug |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| Verifiedfields = verified |
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| UNII = 42O8UF5CJB |
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| Watchedfields = verified |
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| verifiedrevid = 437142357 |
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| verifiedrevid = 444354364 |
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| ImageFileL1 = Fasoracetam.svg |
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| ImageSizeL1 = 125px |
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| drug_name = |
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| image = Fasoracetam.svg |
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| ImageFileR1 = Fasoracetam3d.png |
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| ImageSizeR1 = 100px |
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| width = 200px |
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| image2 = Fasoracetam3d.png |
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| IUPACName = (5R)-5-(piperidine-1-carbonyl) pyrrolidin-2-one |
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| OtherNames = |
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| width2 = 125px |
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| caption = |
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| Section1 = {{Chembox Identifiers |
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<!-- Clinical data --> |
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| pronounce = |
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| Drugs.com = |
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| MedlinePlus = |
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| dependency_liability = |
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| routes_of_administration = ] |
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| class = ] |
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| ATC_prefix = |
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<!-- Legal status --> |
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| legal_US = Not FDA-approved |
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| legal_AU = S4 |
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| legal_status = |
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<!-- Pharmacokinetic data --> |
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| bioavailability = 79–97% (animals)<ref name="Malykh2010" /> |
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| protein_bound = |
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| metabolism = |
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| metabolites = |
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| onset = |
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| elimination_half-life = 4–6.5{{nbsp}}hours<ref name="Malykh2010" /> |
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| duration_of_action = |
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| excretion = |
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<!-- Identifiers --> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 110958-19-5 |
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| CAS_supplemental = |
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| PubChem = 198695 |
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| PubChem = 198695 |
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| IUPHAR_ligand = |
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| DrugBank = DB16163 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 171980 |
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| ChemSpiderID = 171980 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 42O8UF5CJB |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C13311 |
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| KEGG = C13311 |
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| ChEBI = 31592 |
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| InChI = 1/C10H16N2O2/c13-9-5-4-8(11-9)10(14)12-6-2-1-3-7-12/h8H,1-7H2,(H,11,13)/t8-/m1/s1 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = GOWRRBABHQUJMX-MRVPVSSYBL |
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| ChEMBL = 2106179 |
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| SMILES1 = O=C(N1CCCCC1)2NC(=O)CC2 |
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| NIAID_ChemDB = |
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| PDB_ligand = |
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| synonyms = AEVI-001; AEVI-004; LAM-105; MDGN-001; NB-001; NFC-1; NS-105; (5''R'')-5-Oxo-<small>D</small>-prolinepiperidinamide |
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<!-- Chemical data --> |
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| IUPAC_name = (5''R'')-5-(piperidine-1-carbonyl)pyrrolidin-2-one |
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| C=10 | H=16 | N=2 | O=2 |
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| SMILES = C1CCN(CC1)C(=O)2CCC(=O)N2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H16N2O2/c13-9-5-4-8(11-9)10(14)12-6-2-1-3-7-12/h8H,1-7H2,(H,11,13)/t8-/m1/s1 |
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| StdInChI = 1S/C10H16N2O2/c13-9-5-4-8(11-9)10(14)12-6-2-1-3-7-12/h8H,1-7H2,(H,11,13)/t8-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GOWRRBABHQUJMX-MRVPVSSYSA-N |
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| StdInChIKey = GOWRRBABHQUJMX-MRVPVSSYSA-N |
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| CASNo =110958-19-5 |
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| ATCCode_prefix = |
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| ATCCode_suffix = |
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| SMILES= C1CCN(CC1)C(=O)C2CCC(=O)N2 }} |
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| Section2 = {{Chembox Properties |
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| Formula = | C=10 | H=16 | N=2 | O=2 |
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| MolarMass = 196.246 g/mol |
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| Section5 = {{Chembox Pharmacology |
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| AdminRoutes = Oral |
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}} |
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'''Fasoracetam''' ({{Abbrlink|INN|International Nonproprietary Name}}) is an ] of the ] group which was never marketed.<ref name="Malykh2010">{{cite journal | vauthors = Malykh AG, Sadaie MR | title = Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders | journal = Drugs | volume = 70 | issue = 3 | pages = 287–312 | date = February 2010 | pmid = 20166767 | doi = 10.2165/11319230-000000000-00000 | s2cid = 12176745 }}</ref><ref name="GualtieriManettiRomanelli2002">{{cite journal | vauthors = Gualtieri F, Manetti D, Romanelli MN, Ghelardini C | title = Design and study of piracetam-like nootropics, controversial members of the problematic class of cognition-enhancing drugs | journal = Current Pharmaceutical Design | volume = 8 | issue = 2 | pages = 125–138 | date = 2002 | pmid = 11812254 | doi = 10.2174/1381612023396582 }}</ref><ref name="ConnollyGlessnerKao2015">{{cite journal | vauthors = Connolly JJ, Glessner JT, Elia J, Hakonarson H | title = ADHD & Pharmacotherapy: Past, Present and Future: A Review of the Changing Landscape of Drug Therapy for Attention Deficit Hyperactivity Disorder | journal = Therapeutic Innovation & Regulatory Science | volume = 49 | issue = 5 | pages = 632–642 | date = September 2015 | pmid = 26366330 | pmc = 4564067 | doi = 10.1177/2168479015599811 }}</ref> It is a putative ] that failed to show sufficient ] in ]s for ].<ref name="ConnollyGlessnerKao2015" /> The drug was also subsequently ] for treatment of a variety of other conditions, such as ] (ADHD), but effectiveness for ADHD was disappointing<ref name="NageyeCortese2019" /> and development of fasoracetam for most other conditions has been discontinued as well.<ref name="AdisInsight-Avalo" /><ref name="AdisInsight-Nobias" /><ref name="AdisInsight-Avalo-Co-Crystal" /><ref>{{cite journal|title=Recommended INN List 40|journal=WHO Drug Information|date=1998|volume=12|issue=2|url=https://mednet-communities.net/inn/db/media/docs/r-innlist40.pdf}}</ref> In any case, it remains under development for treatment of ].<ref name="AdisInsight-Nobias" /> |
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'''Fasoracetam''' is a ] drug of the ] family. |
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==Pharmacology== |
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{{Racetams}} |
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Fasoracetam appears to modulate and stimulate all three groups of ]s (mGluRs).<ref name="ConnollyGlessnerKao2015" /><ref name="Malykh2010" /> It has been found to improve certain aspects of cognitive function in ].<ref name="ConnollyGlessnerKao2015" /><ref name="Malykh2010" /> The drug is ] and is ] mostly unchanged in ].<ref name="Malykh2010" /><ref name="ConnollyGlessnerKao2015" /> |
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==Chemistry== |
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Fasoracetam is a ] and a ] of ].<ref name="Malykh2010" /><ref name="GualtieriManettiRomanelli2002" /> |
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==History== |
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Fasoracetam was developed in the late 1980s.<ref name="ConnollyGlessnerKao2015" /> It was discovered by scientists at the Japanese pharmaceutical company Nippon Shinyaku, which brought it through ] for ], and abandoned it due to lack of ].<ref name="ConnollyGlessnerKao2015" /><ref name="Hoskowitz2017">{{cite book|last1=Moskowitz|first1=D. H.|title=Finding the Genetic Cause and Therapy for ADHD, Autism and 22q|date=2017|publisher=BookBaby (self published)|isbn=9781483590981|url=https://books.google.com/books?id=LSrlDQAAQBAJ&pg=PT117|language=en}}</ref> Subsequently, fasoracetam was repurposed for treatment of ADHD and other indications.<ref name="ConnollyGlessnerKao2015" /><ref name="AdisInsight-Avalo" /><ref name="AdisInsight-Nobias" /><ref name="AdisInsight-Avalo-Co-Crystal" /> |
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Scientists at ] led by Hakon Hakonarson have studied fasoracetam's potential use in ].<ref name="ConnollyGlessnerKao2015" /> Hakonarson's company neuroFix tried to bring the drug to market for this use; neuroFix acquired Nippon Shinyaku's clinical data as part of its efforts.<ref name="Hoskowitz2017" /><ref name="SeekingAlpha2016" /> neuroFix was acquired by Medgenics in 2015.<ref name="SeekingAlpha2016" /> Medgenics changed its name to Aevi Genomic Medicine in 2016.<ref>{{cite web | title=Press Release: Medgenics, Inc. Announces Name Change to Aevi Genomic Medicine, Inc. | url=http://www.prnewswire.com/news-releases/medgenics-inc-announces-name-change-to-aevi-genomic-medicine-inc-300378599.html | publisher=Aevi via MarketWired|date=16 December 2016}}</ref> |
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{{nervous-system-drug-stub}} |
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Clinical trials in adolescents with ADHD who also have mGluR mutations started in 2016.<ref name="SeekingAlpha2016">{{cite news | title=Medgenics: NFC-1 Could Be A Key Future Revenue Driver. | url=https://seekingalpha.com/article/4010894-medgenics-nfcminus-1-key-future-revenue-driver | author=Sharma, B.| newspaper=Seeking Alpha | date=7 October 2016 }}</ref> While fasoracetam may be effective in the treatment of ADHD in people with specific mGluR mutations, these represent around 10% of total ADHD cases, and fasoracetam is likely ineffective in all other cases.<ref name="pmid29339723"/><ref>{{Cite journal|last=Tardner|first=P|title=Fasoracetam as a treatment for ADHD: A systematic review of available clinical data|url=https://www.ijest.org/fasoracetam-treatment-adhd-a-systematic-review/|date=2020-09-09|journal=International Journal of Environmental Science & Technology|language=en-US}}</ref> Studies showing improvements in cognitive function from fasoracetam have exclusively been done on rodents.<ref name="pmid29339723">{{cite journal | vauthors = Elia J, Ungal G, Kao C, Ambrosini A, De Jesus-Rosario N, Larsen L, Chiavacci R, Wang T, Kurian C, Titchen K, Sykes B, Hwang S, Kumar B, Potts J, Davis J, Malatack J, Slattery E, Moorthy G, Zuppa A, Weller A, Byrne E, Li YR, Kraft WK, Hakonarson H | title = Fasoracetam in adolescents with ADHD and glutamatergic gene network variants disrupting mGluR neurotransmitter signaling | journal = Nature Communications | volume = 9 | issue = 1 | pages = 4 | date = January 2018 | pmid = 29339723 | pmc = 5770454 | doi = 10.1038/s41467-017-02244-2 | bibcode = 2018NatCo...9....4E }}</ref> |
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==Society and culture== |
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===Legality=== |
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====Australia==== |
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Fasoracetam is a schedule 4 substance in Australia under the ].<ref name="PoisonsStandard2020">. comlaw.gov.au</ref> A schedule 4 substance is classified as "Prescription Only Medicine, or Prescription Animal Remedy – Substances, the use or supply of which should be by or on the order of persons permitted by State or Territory legislation to prescribe and should be available from a pharmacist on prescription."<ref name="PoisonsStandard2020" /> |
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==Research== |
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Fasoracetam was originally developed for treatment of ] related to ].<ref name="ConnollyGlessnerKao2015" /> It reached ] ]s for this indication.<ref name="ConnollyGlessnerKao2015" /> However, development was discontinued due to lack of effectiveness and fasoracetam was never marketed.<ref name="ConnollyGlessnerKao2015" /> |
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Fasoracetam (developmental code names AEVI-001, LAM-105, MDGN-001, NFC-1, NS-105) was under development by Avalo Therapeutics (previously Cerecor) for the treatment of ] (ADHD), ], ]s, ], and ].<ref name="AdisInsight-Avalo">{{cite web | title=Fasoracetam - Avalo Therapeutics | work = AdisInsight | publisher = Springer Nature Switzerland AG | date=30 August 2021 | url=https://adisinsight.springer.com/drugs/800003134 | access-date=1 October 2024}}</ref> However, development for all indications was discontinued by 2018.<ref name="AdisInsight-Avalo" /> The drug (developmental code name NB-001) is also under development by Nobias Therapeutics for the treatment of DiGeorge syndrome and is in ] ]s for this use as of October 2023.<ref name="AdisInsight-Nobias">{{cite web | title=Fasoracetam - Nobias Therapeutics | work = AdisInsight | publisher = Springer Nature Switzerland AG | date=17 October 2023 | url=https://adisinsight.springer.com/drugs/800067855 | access-date=1 October 2024}}</ref> A ] form of fasoracetam (developmental code name AEVI-004) is under development by Avalo Therapeutics for the treatment of ADHD, autistic disorder, and ] as well.<ref name="AdisInsight-Avalo-Co-Crystal">{{cite web | title=Co-crystallised fasoracetam - Avalo Therapeutics | work = AdisInsight | publisher = Springer Nature Switzerland AG | date=28 April 2023 | url=https://adisinsight.springer.com/drugs/800052566 | access-date=1 October 2024}}</ref> However, no recent development has been reported for these indications as of April 2023.<ref name="AdisInsight-Avalo-Co-Crystal" /> Pharmaceutical developmental code names of fasoracetam include |
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The results of clinical studies of fasoracetam for ADHD have been disappointing.<ref name="NageyeCortese2019">{{cite journal | vauthors = Nageye F, Cortese S | title = Beyond stimulants: a systematic review of randomised controlled trials assessing novel compounds for ADHD | journal = Expert Review of Neurotherapeutics | volume = 19 | issue = 7 | pages = 707–717 | date = July 2019 | pmid = 31167583 | doi = 10.1080/14737175.2019.1628640 | url = https://eprints.soton.ac.uk/431813/1/ERN_main_text_R1_BLACK.doc }}</ref> |
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== References == |
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{{Reflist}} |
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{{Racetams}} |
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