5-Amino-3-oxopentansaeure
Aminolevulinic Acid Hydrochloride
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Grundinformationen
- CAS
5451-09-2- Standard-SMILES
Cl.NCC(=O)CCC(=O)O- InChIKey
ZLHFONARZHCSET-UHFFFAOYSA-N- Summenformel
- C5H10ClNO3
- Durchschnittliche Molmasse
- 167,59 g/mol
- Monoisotopische Masse
- 167,03492086
Überblick
5-aminolevulinic acid hydrochloride is a hydrochloride that is the monohydrochloride of 5-aminolevulinic acid. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp. It has a role as an antineoplastic agent, a photosensitizing agent, a dermatologic drug and a prodrug. It contains a 5-ammoniolevulinic acid.
Namen und Bezeichner
- Bevorzugter Name
- Aminolevulinic Acid Hydrochloride
- IUPAC
- 5-amino-4-oxopentanoic acid;hydrochloride
- Lokaler Name
- 5-Amino-3-oxopentansaeure
- Englischer Name
- 5-Aminolevulinic acid hydrochloride
- Summenformel
- C5H10ClNO3
- Molmasse
- 167.59
Namen und Synonyme
5-Aminolevulinic acid hydrochloride5451-09-2Aminolevulinic acid hydrochloride5-Amino-4-oxopentanoic acid hydrochlorideLevulanLevulan Kerastickdelta-Aminolevulinic acid hydrochlorideAminolevulinic Acid HClAmeluzAlaglioGleolanAlabel
Weitere Namen anzeigen
5-Ala5-AMINOLEVULINIC ACID HCL5-AminolevulinicGliolaninic acid hydrochLevuL5-AminoL5-Amino-3-oxopentanoic acid (hydrochloride)
AlaCareDTXSID5045914Pentanoic acid, 5-amino-4-oxo-, hydrochlorideV35KBM8JGRNSC-18509NPC-075-AMINO-4-OXOPENTANOIC ACID HCLDTXCID3025914
Datenbank-Bezeichner
- CAS
5451-09-2- PubChem CID
- 123608
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- Polarare Oberfläche (TPSA)
- 80,4 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 121
Experimentelle und physikochemische Eigenschaften
Human Drugs
Breast Feeding; Lactation; Milk, Human; Dermatologic Agents; Photosensitizing Agents
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Schmelzpunkt
- 150 °C · ~150 °C (dec.)
- Flammpunkt
- 155 · 155-157°C
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 2 O: · H2O: 50 mg/mL
- Aggregatzustand
- powder
- Farbe
- White to pale yellow
- PH
- pH (10g/l, 25℃) : 2.5～3.0
- Wasserlöslichkeit
- Soluble in dimethyl sulfoxide, methanol and water.
- Decomposition
- 155 · 155-157 ºC
- Merck
- 14 · 14,446
- BRN
- 3690651 · 3690651
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
Regulatory InformationPentanoic acid, 5-amino-4-oxo-, hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Pentanoic acid, 5-amino-4-oxo-, hydrochloride: Environment tier I assessment
Toxikologische Informationen
Exposure RoutesOral bioavailability is 50-60%.
Toxicity Summary
According to the presumed mechanism of action, photosensitization following application of aminolevulinic acid (ALA) topical solution occurs through the metabolic conversion of ALA to protoporphyrin IX (PpIX), which accumulates in the skin to which aminolevulinic acid has been applied. When exposed to light of appropriate wavelength and energy, the accumulated PpIX produces a photodynamic reaction, a cytotoxic process dependent upon the simultaneous presence of light and oxygen. The absorption of light results in an excited state of the porphyrin molecule, and subsequent spin transfer from PpIX to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals. Photosensitization of actinic (solar) keratosis lesions using aminolevulinic acid, plus illumination with the BLU-UTM Blue Light Photodynamic Therapy Illuminator (BLU-U), is the basis for aminolevulinic acid photodynamic therapy (PDT).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
Chemie und Industrie
Pharmakologische Informationen
Metabolism/MetabolitesFollowing topical administration, synthesis into protoporphyrin IX takes place in situ in the skin.
Half Life: Mean half-life is 0.70 ± 0.18 h after the oral dose and 0.83 ± 0.05 h after the intravenous dose.
FDA Pharmacological Classification
AMINOLEVULINIC ACID HYDROCHLORIDE
Optical Imaging Agent [EPC]; Porphyrin Precursor [EPC]; Porphyrinogens [CS]; Fluorescence Contrast Activity [MoA]
MeSH Pharmacological Classification
Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.
Verwendung und Herstellung
UsesAminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.
Anwendungen
Verwenden5-Aminolevulinic acid hydrochloride finds an important role as a precursor in the synthesis of tetrapyrroles such as chlorophyll and heme. It is widely utilized in photodynamic therapy of diseases namely, Pagets disease and human papillomavirus (HPV) infection-associated cervical condylomata acuminata.
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