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	Racemic: 99-15-0^Y S (-): 19764-30-8^Y R (+): 1188-21-2^Y
3D model (JSmol)	Racemic: Interactive image
3DMet	Racemic: B00487
Beilstein Reference	1724849 (S)-(-)
ChEBI	Racemic: CHEBI:17786^Y
ChEMBL	Racemic: ChEMBL174357^Y S (-): ChEMBL56021^Y
ChemSpider	Racemic: 1918^Y S (-): 64075^Y R (+): 1042393^Y
EC Number	Racemic: 202-734-9
Gmelin Reference	985259 (S)-(-)
KEGG	Racemic: D07350^Y
MeSH	acetylleucine
PubChem CID	Racemic: 1995 S (-): 70912 R (+): 1241420
UNII	Racemic: K76S41V71X^Y
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
ATC code	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] IntraBio is also investigating acetylleucine for the treatment of common inherited and acquired neurological diseases including Lewy body dementia,[7] amyotrophic lateral sclerosis, restless legs syndrome, multiple sclerosis, and migraine[8] Acetylleucine has received orphan drug designations from the U.S. Food & Drug Administration (FDA)[9][10][11][12] and the European Commission.[13][14][15][16]

See also

• Leucine

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. Passmore, Peter (2014-04-15). "A clinical trial to test amlodipine as a new treatment for vascular dementia". doi:10.1186/isrctn31208535. Cite journal requires |journal= (help)
8. 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.
9. "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
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. "Public Health - European Commission". Union Register of medicinal products. 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.