Fasoracetam

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Fasoracetam

  • Molecular FormulaC10H16N2O2
  • Average mass196.246 Da
(5R)-5-(1-Piperidinylcarbonyl)-2-pyrrolidinone
(5R)-5-(Piperidin-1-ylcarbonyl)pyrrolidin-2-one
110958-19-5 [RN]
2-Pyrrolidinone, 5-(1-piperidinylcarbonyl)-, (5R)-
7708, UNII: 42O8UF5CJB
NS 105
N-(5-Oxo-D-prolyl)piperidine
(+)-1-(((R)-5-Oxo-2-pyrrolidinyl)carbonyl)piperidine
AEVI GENOMIC MEDICINE, INC. [US/US]; 435 Devon Park Drive, Suite 715 Wayne, Pennsylvania 19087, US

Fasoracetam is a research chemical of the racetam family.[3] It is a putative nootropic that failed to show sufficient efficacy in clinical trials for vascular dementia. It is currently being studied for its potential use for attention deficit hyperactivity disorder.[2][4]

Fasoracetam appears to agonize all three groups of metabotropic glutamate receptors and has improved cognitive function in rodent studies.[5] It is orally bioavailable and is excreted mostly unchanged via the urine.[6]

Fasoracetam was discovered by scientists at the Japanese pharmaceutical company Nippon Shinyaku, which brought it through Phase 3 clinical trials for vascular dementia, and abandoned it due to lack of efficacy.[5][7]

Scientists at Children’s Hospital of Philadelphia led by Hakon Hakonarson have studied fasoracetam’s potential use in attention deficit hyperactivity disorder.[5] Hakonarson started a company called neuroFix Therapeutics to try to bring the drug to market for this use; neuroFix acquired Nippon Shinyaku’s clinical data as part of its efforts.[7][8] neuroFix was acquired by Medgenics in 2015.[8] Medgenics changed its name to Aevi Genomic Medicine in 2016.[9] Clinical trials in adolescents with ADHD who also have mGluR mutations started in 2016.[8]

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SYN

str1-1

Chemistry – A European Journal, 24(27), 7033-7043; 2018

PAPER

Chemistry – A European Journal (2018), 24, (27), 7033-7043

https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201800372

image

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

Patent

WO-2019143829

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2019143829&tab=PCTDESCRIPTION&_cid=P10-JYNTFB-68856-1

Novel crystalline forms of fasoracetam , processes for their preparation and compositions comprising them are claimed.

PATENT

WO2019143824

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2019143824&_cid=P10-JYNTH3-69052-1

Novel crystalline and cocrystal forms of fasoracetam (R-fasoracetam) and a co-former, processes for their preparation and compositions comprising them are claimed. Also claims are novel crystalline forms of fasoracetam and 4-aminobenzoic acid or trimesic acid or R- ibuprofen or phloroglucinol or methyl-3,4-5-trihydroxybenzoate or ethyl gallate or phthalic acid or 6-hydroxy-2-napthoic acid or 4-nitrobenzoic acid or 2-indole-3-acetic acid or urea and their monohydrate and dihydrate (designated as Form B).

PATENT

WO2018195184

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2018195184&_cid=P10-JYNTI8-69210-1

claiming methods for diagnosing and treating ADHD in biomarker positive subjects, assigned to Aevi Genomics Medicine, Inc and The Childrens Hospital of Philadelphia , naming different teams.

PAPER

https://advances.sciencemag.org/content/3/9/e1701028

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References

  1. ^ FDA/NIH Substance registration system. Page accessed March 21, 2016
  2. Jump up to:a b “Drug Profile Fasoracetam”.
  3. ^ “5-oxo-D-prolinepiperidinamide monohydrate – Compound Summary”. Retrieved 21 July 2013.
  4. ^ “Recommended INN List 40” (PDF)WHO Drug Information12 (2). 1998.
  5. Jump up to:a b c Connolly, J; Glessner, J; Kao, C; Elia, J; Hakonarson, H. “ADHD & Pharmacotherapy: Past, Present and Future: A Review of the Changing Landscape of Drug Therapy for Attention Deficit Hyperactivity Disorder”Ther Innov Regul Sci49 (5): 632–642. doi:10.1177/2168479015599811PMC 4564067PMID 26366330.
  6. ^ Malykh, AG; Sadaie, MR (12 February 2010). “Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders”. Drugs70 (3): 287–312. doi:10.2165/11319230-000000000-00000PMID 20166767.
  7. Jump up to:a b Moskowitz, D. H. (2017). Finding the Genetic Cause and Therapy for ADHD, Autism and 22q. BookBaby (self published). ISBN 9781483590981.
  8. Jump up to:a b c Sharma, B. “Medgenics: NFC-1 Could Be A Key Future Revenue Driver”.
  9. ^ “Press Release: Medgenics, Inc. Announces Name Change to Aevi Genomic Medicine, Inc”. Aevi via MarketWired. 16 December 2016.
Fasoracetam
Fasoracetam.svg
Fasoracetam3d.png
Names
IUPAC name

(5R)-5-(Piperidine-1-carbonyl)pyrrolidin-2-one
Other names

(5R)-5-Oxo-D-prolinepiperidinamide monohydrate, NS-105, AEVI-001, LAM 105, MDGN-001, NFC 1[1][2]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
Properties
C10H16N2O2
Molar mass 196.250 g·mol−1
Pharmacology
Oral
Legal status
  • US: Not FDA approved
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

/////////Fasoracetam, attention deficit hyperactivity disorder, NS 105, Phase 3,  vascular dementia

C1CCN(CC1)C(=O)[C@H]2CCC(=O)N2

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