N-Acetylleucin
N-Acetyl-L-leucine
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Grundinformationen
- CAS
1188-21-2- Standard-SMILES
CC(=O)N[C@@H](CC(C)C)C(=O)O- InChIKey
WXNXCEHXYPACJF-ZETCQYMHSA-N- Summenformel
- C8H15NO3
- Durchschnittliche Molmasse
- 173,21 g/mol
- Monoisotopische Masse
- 173,10519334
Überblick
N-acetyl-L-leucine is the N-acetyl derivative of L-leucine. It has a role as a metabolite. It is a N-acetyl-L-amino acid and a L-leucine derivative. It is a conjugate acid of a N-acetyl-L-leucinate. It is an enantiomer of a N-acetyl-D-leucine.
Namen und Bezeichner
- Bevorzugter Name
- N-Acetyl-L-leucine
- IUPAC
- (2S)-2-acetamido-4-methylpentanoic acid
- Lokaler Name
- N-Acetylleucin
- Englischer Name
- N-Acetyl-L-leucine
- Summenformel
- C8H15NO3
- Molmasse
- 173.21
Namen und Synonyme
N-Acetyl-L-leucine1188-21-2N-AcetylleucineL-Acetylleucine(S)-2-Acetamido-4-methylpentanoic acidN-acetyl-leucineLevacetylleucine(2S)-2-acetamido-4-methylpentanoic acidLeucine, N-acetyl-, L-N-ACETYL-L-(-)-LEUCINEn-acetyl leucineAQNEURSA
Weitere Namen anzeigen
AC-LEU-OHACETYL-L-LEUCINEACETYL-DL-LEUCINEAC-DL-LEU-OHN-Ac-L-Leu-OHAc-L-Leu-OHn-acetyl-l-leucin(S)-N-Acetylleucine
E915HL7K2ONSC-206316ACETYLLEUCINE, (S)-CHEBI:17786RefChem:927004DTXCID00209990214-706-3DTXSID40859594
Datenbank-Bezeichner
- CAS
1188-21-2、99-15-0- PubChem CID
- 70912
- DTXSID
DTXSID6045870
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 0,5
- Polarare Oberfläche (TPSA)
- 66,4 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 177
Experimentelle und physikochemische Eigenschaften
LogP0.79
Solubility8.1 mg/mL at 25 °C
Human Drugs
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine (Orphan designations)
FDA approved drugs -> Active ingredient
Physical DescriptionSolid
Collision Cross Section
140.5 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
160.24 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
150.1 Ų [M+Na]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 187 · 187-190 °C(lit.)
- Siedepunkt
- 303.86 °C · 303.86°C (rough estimate)
- Dichte
- 1.1599 · 1.1599 (rough estimate)
- Brechungsindex
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 5.4% (2 of 37) of reports.
Warning
H315 (91.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 37 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (91.9%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29241900
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- hazard_class
- IRRITANT
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC CodeN - Nervous system
PharmacodynamicsThe pharmacodynamics of levacetylleucine are not well characterized. There does not appear to be a relationship between increasing levacetylleucine exposure and clinical efficacy.
Mechanism of Action
Following oral administration, levacetylleucine is taken up via ubiquitously expressed monocarboxylate transporters and distributed to all body tissues. It enters enzyme-controlled pathways that correct metabolic dysfunction and improves adenosine triphosphate (ATP) energy production. The normalization of energy metabolism ameliorates mitochondrial and lysosomal dysfunction and leads to a reduction in the storage of unesterified cholesterol and sphingolipids. Levacetylleucine has also been shown to normalize neuronal membrane potentials in a guinea pig model, thereby improving cellular signaling processes and restoring and protecting neuronal circuits. The specific molecular target of levacetylleucine in the context of Niemann-Pick disease type C (NPC) is unknown.
Biological Half-LifeThe half-life of levacetylleucine is approximately 1 hour.
Metabolism/MetabolitesLevacetylleucine is metabolized into acetate and L-leucine by ubiquitously expressed enzymes.
FDA Pharmacological Classification
E915HL7K2O
LEVACETYLLEUCINE
Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors
Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors
Mechanisms of Action [MoA] - Bile Salt Export Pump Inhibitors
Mechanisms of Action [MoA] - Organic Anion Transporter 1 Inhibitors
Absorption, Distribution and Excretion
The Cmaxand AUC0-24h of levacetylleucine following oral administration were 8.3 μg/mL and 33.2 h*μg/mL, respectively. The time to maximum concentration (Tmax) is approximately 1 hour.
Zugehörige Reaktionen
29
Notizen zur Verbindung
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