ACETYLLEUCINE

Acetylleucine
	; (S)-(−)-N-Acetyl-leucine
Names
	IUPAC name 2-Acetamido-4-methylpentanoic acid
	Other names N-Acetylleucine; N-Acetyl-L-Leucine
Identifiers
CAS Number	Racemic: 99-15-0 ; S (−): 1188-21-2 ; R (+): 19764-30-8 ;
3D model ( JSmol)	Racemic: Interactive image;
3DMet	Racemic: B00487;
Beilstein Reference	1724849 (S)-(−)
ChEBI	Racemic: CHEBI:17786 ;
ChEMBL	Racemic: ChEMBL174357 ; S (−): ChEMBL56021 ;
ChemSpider	Racemic: 1918 ; S (−): 64075 ; R (+): 1042393 ;
EC Number	Racemic: 202-734-9;
Gmelin Reference	985259 (S)-(−)
KEGG	Racemic: D07350 ;
MeSH	acetylleucine
PubChem CID	Racemic: 1995; S (−): 70912; R (+): 1241420;
UNII	Racemic: K76S41V71X ; S (−): E915HL7K2O ; R (+): 91WU82GA22 ;
	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) Key: WXNXCEHXYPACJF-UHFFFAOYSA-N ;
	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 a modified amino acid used in the treatment of vertigo^[2] and cerebellar ataxia.

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]

References

^ "N-Acetyl-DL-leucine". PubChem Open Chemistry Database. Retrieved 26 Mar 2017.
^ "N07CA04 (acetylleucine)". WHO Collaborating Centre for Drug Statistics Methodology. Norwegian Institute of Public Health. 19 Dec 2016. Retrieved 26 Mar 2017.
^ "IntraBio". Archived from the original on 2019-08-01. Retrieved 2019-08-01.
^ "N-Acetyl-L-Leucine for Niemann-Pick Disease, Type C (NPC) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2019-08-01.
^ "N-Acetyl-L-Leucine for GM2 Gangliosdisosis (Tay-Sachs and Sandhoff Disease) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2019-08-01.
^ "N-Acetyl-L-Leucine for Ataxia-Telangiectasia (A-T) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2019-08-01.
^ "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.
^ 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)
^ 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.
^ "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
^ "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
^ "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
^ "Search Orphan Drug Designations and Approvals". www.accessdata.fda.gov. Retrieved 2019-08-03.
^ "Public Health - European Commission". Union Register of medicinal products. Retrieved 2019-08-03.
^ "Public Health - European Commission". Union Register of medicinal products. Retrieved 2019-08-03.
^ "Public Health - European Commission". Union Register of medicinal products. Retrieved 2019-08-03.
^ "Public Health - European Commission". Union Register of medicinal products. Retrieved 2019-08-03.

[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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Names
(S)-(−)-N-Acetyl-leucine
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 (−): 1188-21-2^Y R (+): 19764-30-8^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 S (−): E915HL7K2O^Y R (+): 91WU82GA22^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 (pK_a)	3.666
Basicity (pK_b)	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