5-Amino-3-oxopentansaeure

Aminolevulinic Acid Hydrochloride

HCID 123608CAS 5451-09-2

Grundinformationen

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
DTXSID
DTXSID5045914
ChEMBL
CHEMBL1200582
ChEBI
CHEBI:132969
UNII
V35KBM8JGR

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
80,4 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
4
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

Human Drugs · 5 Einträge

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

Sicherheit und Regulatorisches

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 · 1 Eintrag

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

F
3-8-10
wgk
3
hs_code
29224999
RTECS-Nr.
OI1640000
risk_code
36/37/38-66-20/21/22-36/38
hazard_code
Xi,Xn

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 · 2 Einträge

AMINOLEVULINIC ACID HYDROCHLORIDE

Optical Imaging Agent [EPC]; Porphyrin Precursor [EPC]; Porphyrinogens [CS]; Fluorescence Contrast Activity [MoA]

MeSH Pharmacological Classification · 1 Eintrag

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 · 1 Eintrag

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.

Anbieter50 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.

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