Wikipedia

Acetylleucine

Acetylleucine (N-acetyl-leucine) is a modified leucine amino acid used in the treatment of vertigo[2] and cerebellar ataxia.

Acetylleucine
Stereo, skeletal model of acetylleucine (S)
(S)-(−)-N-Acetyl-leucine
Names
IUPAC name
2-Acetamido-4-methylpentanoic acid[1]
Other names
N-Acetylleucine; N-Acetyl-L-Leucine
Identifiers
3D model (JSmol)
3DMet
1724849 (S)-(−)
ChEBI
ChEMBL
ChemSpider
EC Number
  • Racemic: 202-734-9
985259 (S)-(−)
KEGG
MeSH acetylleucine
UNII
  • 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) checkY
    Key: WXNXCEHXYPACJF-UHFFFAOYSA-N checkY
  • Racemic: CC(C)CC(NC(C)=O)C(O)=O
Properties
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).

Two forms exist: acetyl-DL-leucine (sold under the brand Tanganil, among others) and N-acetyl-L-leucine (levacetylleucine).[3]

Acetylleucine is also being developed as a possible treatment for several neurological disorders by IntraBio Inc.[4] Clinical trials with acetylleucine for the treatment of three orphan, fatal, neurodegenerative disorders are underway: Niemann-Pick disease type C,[5] GM2 gangliosidoses (Tay-Sachs and Sandhoff diseases),[6] and ataxia–telangiectasia.[7] In 2020, IntraBio announced the successful multinational clinical trial results of the Niemann-Pick type C clinical trial.[8] IntraBio is also investigating acetylleucine for the treatment of common inherited and acquired neurological diseases including Lewy body dementia,[9] amyotrophic lateral sclerosis, restless legs syndrome, multiple sclerosis, and migraine[10] Acetylleucine has received orphan drug designations from the U.S. Food & Drug Administration (FDA)[11][12][13][14] and the European Commission.[15][16][17][18]

References

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  1. ^ "N-Acetyl-DL-leucine". PubChem Open Chemistry Database. Retrieved 26 March 2017.
  2. ^ "N07CA04 (acetylleucine)". WHO Collaborating Centre for Drug Statistics Methodology. Norwegian Institute of Public Health. 19 December 2016. Retrieved 26 March 2017.
  3. ^ Oertel WH, Janzen A, Henrich MT, Geibl FF, Sittig E, Meles SK, et al. (2 September 2024). "Acetyl-DL-leucine in two individuals with REM sleep behavior disorder improves symptoms, reverses loss of striatal dopamine-transporter binding and stabilizes pathological metabolic brain pattern—case reports". Nature Communications. 15 (1): 7619. doi:10.1038/s41467-024-51502-7. ISSN 2041-1723. PMC 11369233. PMID 39223119.
  4. ^ "IntraBio". Archived from the original on 1 August 2019. Retrieved 1 August 2019.
  5. ^ "N-Acetyl-L-Leucine for Niemann-Pick Disease, Type C (NPC) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 1 August 2019.
  6. ^ "N-Acetyl-L-Leucine for GM2 Gangliosdisosis (Tay-Sachs and Sandhoff Disease) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 1 August 2019.
  7. ^ "N-Acetyl-L-Leucine for Ataxia-Telangiectasia (A-T) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 1 August 2019.
  8. ^ "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 1 August 2021.
  9. ^ Passmore P (15 April 2014). "A clinical trial to test amlodipine as a new treatment for vascular dementia". doi:10.1186/isrctn31208535. {{cite journal}}: Cite journal requires |journal= (help)
  10. ^ Strupp M, Bayer O, Feil K, Straube A (1 February 2019). "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.
  11. ^ "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 3 August 2019.
  12. ^ "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 3 August 2019.
  13. ^ "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 3 August 2019.
  14. ^ "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 3 August 2019.
  15. ^ "Public Health - European Commission". Union Register of medicinal products. Retrieved 3 August 2019.
  16. ^ "Public Health - European Commission". Union Register of medicinal products. Retrieved 3 August 2019.
  17. ^ "Public Health - European Commission". Union Register of medicinal products. Retrieved 3 August 2019.
  18. ^ "Public Health - European Commission". Union Register of medicinal products. Retrieved 3 August 2019.
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