5-Aminolevulinic acid hexyl ester

HCID 6433083CAS 140898-97-1

Grundinformationen

Standard-SMILES
CCCCCCOC(=O)CCC(=O)CN
InChIKey
RYQOILLJDKPETL-UHFFFAOYSA-N
Summenformel
C11H21NO3
Durchschnittliche Molmasse
215,29 g/mol
Monoisotopische Masse
215,15214353

Überblick

5-aminolevulinic acid hexyl ester is an organonitrogen compound and an organooxygen compound. It is functionally related to a delta-amino acid.

Namen und Bezeichner

Bevorzugter Name
5-Aminolevulinic acid hexyl ester
IUPAC
hexyl 5-amino-4-oxopentanoate
Englischer Name
5-aminolevulinic acid hexyl ester
Summenformel
C11H21NO3
Molmasse
215.29

Namen und Synonyme

5-Aminolevulinic acid hexyl esterhexyl-aminolevulinateALA hexyl esterhexa ALAhexylaminolevulinateRefChem:552965-ALAHEaminolevulinic acid hexylesterHexaminolevulinateHexyl 5-amino-4-oxopentanoate140898-97-1Hexyl 5-aminolevulinate
Weitere Namen anzeigen
Ethyl Acetate Impurity 164
Pentanoic acid, 5-amino-4-oxo-, hexyl esterG7H20TKI67Aminolevulinic acid hexyl esterUNII-G7H20TKI675-Amino-4-oxopentanoic acid hexyl esterstarbld0000848(14C)-hexaminolevulinateHEXAMINOLEVULINATE [MI]

Datenbank-Bezeichner

CAS
140898-97-1
PubChem CID
6433083
DTXSID
DTXSID40161487
ChEMBL
CHEMBL1201784
ChEBI
CHEBI:134892
UNII
G7H20TKI67
Nikkaji
J1.058.793J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,1
Polarare Oberfläche (TPSA)
69,4 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
10
Schwere Atome
15

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Diagnostic Agents; Photosensitizing Agents;

Physikochemische Eigenschaften

Siedepunkt
313.2 · 313.2±22.0 °C(Predicted)
Dichte
1.004 · 1.004±0.06 g/cm3(Predicted)
pka
7.24 · 7.24±0.29(Predicted)

Sicherheit und Regulatorisches

Toxikologische Informationen

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

V - Various

QV - Various

Protein BindingNo evidence of significant binding.
Pharmacodynamics · 1 Eintrag

In vitro studies have shown increased porphyrin fluorescence in normal urothelium after exposure to hexaminolevulinate hydrochloride intravesical solution. In the human bladder, a greater accumulation of porphyrins is proposed in neoplastic or inflamed cells, compared to normal urothelium. After bladder instillation of hexaminolevulinate hydrochloride intravesical solution for approximately 1 hour and subsequent illumination with blue light at wavelengths 360 – 450nm, the porphyrins will fluoresce red.

Mechanism of Action · 1 Eintrag

Hexaminolevulinate is an ester of the heme precursor, aminolevulinic acid. After bladder instillation, hexaminolevulinate enters the bladder mucosa and is proposed to enter the intracellular space of mucosal cells where it is used as a precursor in the formation of the photoactive intermediate protoporphyrin IX (PpIX) and other photoactive porphyrins (PAPs). PpIX and PAPs are reported to accumulate preferentially in neoplastic cells as compared to normal urothelium, partly due to altered enzymatic activity in the neoplastic cells. After excitation with light at wavelengths between 360 and 450 nm, PpIX and other PAPs return to a lower energy level by fluorescing, which can be detected and used for cystoscopic detection of lesions. The fluorescence from tumor tissue appears bright red and demarcated, whereas the background normal tissue appears dark blue. Similar processes may occur in inflamed cells.

Biological Half-LifeBiphasic elimination, with an initial elimination half-life of 39 minutes, followed by a terminal half-life of approximately 76 hours.
Metabolism/MetabolitesRapid metabolism in human blood.

Anbieter5 Anbieter

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