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
Weitere Namen anzeigen
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
- 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
- Stabilität
- Hygroscopic
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN PROTECTINGANTIMICROBIALHAIR CONDITIONINGANTI-SEBUM
- InChI
- 1S/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9;/h1-3,6H2,(H,8,9);1H
- InChIKey
- ZLHFONARZHCSET-UHFFFAOYSA-N
- SMILES
- Cl[H].NCC(=O)CCC(O)=O
- CAS Datenbank
- 5451 · 5451-09-2(CAS DataBase Reference)
Sicherheit und Regulatorisches
Gefahrenhinweise
Toxikologische Informationen
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).
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
- hazard_note
- Irritant
- safety_code
- 26-36/37-37/39-36
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
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
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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
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Ergänzende Hinweise
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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