Acetylleucine

Acetylleucine is a modified amino acid used in the treatment of vertigo[2] and cerebellar ataxia.

Acetylleucine

(S)-(-)-N-Acetyl-leucine
Names
IUPAC name
2-Acetamido-4-methylpentanoic acid[1]
Other names
N-Acetylleucine; N-Acetyl-L-Leucine
Identifiers
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference
 1724849 (S)-(-)
ChEBI
ChEMBL
ChemSpider
EC Number
  • Racemic: 202-734-9
Gmelin Reference
 985259 (S)-(-)
KEGG
MeSH acetylleucine
PubChem CID
UNII
InChI
  • InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12) Y
    Key: WXNXCEHXYPACJF-UHFFFAOYSA-N Y
SMILES
  • Racemic: CC(C)CC(NC(C)=O)C(O)=O
Properties
Chemical formula
 C8H15NO3
Molar mass 173.212 g·mol−1
Appearance White crystals
Melting point −115 to −113 °C; −175 to −172 °F; 158 to 160 K
log P −0.265
Acidity (pKa) 3.666
Basicity (pKb) 10.331
Pharmacology
N07CA04 (WHO)
Related compounds
Related compounds
 ENU
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetylleucine is also being developed as a possible treatment for several neurological disorders by IntraBio Inc.[3] Clinical trials with acetylleucine for the treatment of three orphan, fatal, neurodegenerative disorders are underway: Niemann-Pick disease type C,[4] GM2 gangliosidoses (Tay-Sachs and Sandhoff diseases),[5] and ataxia–telangiectasia.[6] In 2020, IntraBio announced the successful multinational clinical trial results of the Niemann-Pick type C clinical trial.[7] IntraBio is also investigating acetylleucine for the treatment of common inherited and acquired neurological diseases including Lewy body dementia,[8] amyotrophic lateral sclerosis, restless legs syndrome, multiple sclerosis, and migraine[9] Acetylleucine has received orphan drug designations from the U.S. Food & Drug Administration (FDA)[10][11][12][13] and the European Commission.[14][15][16][17]

See also

References
  1. "N-Acetyl-DL-leucine". PubChem Open Chemistry Database. Retrieved 26 Mar 2017.
  2. "N07CA04 (acetylleucine)". WHO Collaborating Centre for Drug Statistics Methodology. Norwegian Institute of Public Health. 19 Dec 2016. Retrieved 26 Mar 2017.
  3. "IntraBio". Archived from the original on 2019-08-01. Retrieved 2019-08-01.
  4. "N-Acetyl-L-Leucine for Niemann-Pick Disease, Type C (NPC) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2019-08-01.
  5. "N-Acetyl-L-Leucine for GM2 Gangliosdisosis (Tay-Sachs and Sandhoff Disease) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2019-08-01.
  6. "N-Acetyl-L-Leucine for Ataxia-Telangiectasia (A-T) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2019-08-01.
  7. "IntraBio Reports Further Detail on Positive Data from IB1001 Multinational Clinical Trial for the Treatment of Niemann-Pick disease Type C". intrabio.com. 19 October 2020. Retrieved 2021-08-01.
  8. Passmore, Peter (2014-04-15). "A clinical trial to test amlodipine as a new treatment for vascular dementia". doi:10.1186/isrctn31208535. {{cite journal}}: Cite journal requires |journal= (help)
  9. Strupp, Michael; Bayer, Otmar; Feil, Katharina; Straube, Andreas (2019-02-01). "Prophylactic treatment of migraine with and without aura with acetyl-dl-leucine: a case series". Journal of Neurology. 266 (2): 525–529. doi:10.1007/s00415-018-9155-6. ISSN 1432-1459. PMID 30547273. S2CID 56148131.
  10. "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
  11. "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
  12. "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
  13. "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
  14. "Public Health - European Commission". Union Register of medicinal products. Retrieved 2019-08-03.
  15. "Public Health - European Commission". Union Register of medicinal products. Retrieved 2019-08-03.
  16. "Public Health - European Commission". Union Register of medicinal products. Retrieved 2019-08-03.
  17. "Public Health - European Commission". Union Register of medicinal products. Retrieved 2019-08-03.
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