Grundinformationen
- Standard-SMILES
COC(=O)CCC(=O)CN- InChIKey
YUUAYBAIHCDHHD-UHFFFAOYSA-N- Summenformel
- C6H11NO3
- Durchschnittliche Molmasse
- 145,16 g/mol
- Monoisotopische Masse
- 145,07389321
Überblick
Methyl 5-aminolevulinate is the methyl ester of 5-aminolevulinic acid. A prodrug, it is metabolised to protoporphyrin IX, a photosensitizer, and is used in the photodynamic treatment of non-melanoma skin cancer (including basal cell carcinoma). Topical application (often as the hydrochloride salt) results in an accumulation of protoporphyrin IX in the skin lesions to which the cream has been applied. Subsequent illumination with red light results in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills the tumour cells. It has a role as an antineoplastic agent, a photosensitizing agent, a dermatologic drug and a prodrug. It is functionally related to a 5-aminolevulinic acid.
Namen und Bezeichner
- Bevorzugter Name
- Methyl Aminolevulinate
- IUPAC
- methyl 5-amino-4-oxopentanoate
- Englischer Name
- D-Aminolevulinicacidmethylesterhydrochloride
- Summenformel
- C6H12ClNO3
- Molmasse
- 181.61738
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
33320-16-0- PubChem CID
- 157922
- DTXSID
DTXSID3048570- ChEMBL
CHEMBL1096562- ChEBI
CHEBI:724125- UNII
- 585NM85KYM
- Nikkaji
- J313.797J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1
- Polarare Oberfläche (TPSA)
- 69,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 133
Experimentelle und physikochemische Eigenschaften
Solubility
Freely soluble
2.20e+02 g/L
Physikochemische Eigenschaften
- LogP
- -0.57 · -0.570 (est)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L01XD03
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Pharmacodynamics
After topical application of methyl aminolevulinate, porphyrins will accumulate intracellularly in the treated skin lesions. The intracellular porphyrins (including PpIX) are photoactive, fluorescing compounds and, upon light activation in the presence of oxygen, singlet oxygen is formed which causes damage to cellular compartments, in particular the mitochondria. Light activation of accumulated porphyrins leads to a photochemical reaction and thereby phototoxicity to the light-exposed target cells.
Mechanism of Action
Photosensitization following application of methyl aminolevulinate cream occurs through the metabolic conversion of methyl aminolevulinate (prodrug) to photoactive porphyrins (PAP), which accumulates in the skin lesions to which the cream has been applied. When exposed to light of appropriate wavelength and energy, the accumulated photoactive porphyrins produce a photodynamic reaction, resulting in a cytotoxic process dependent upon the simultaneous presence of oxygen. The absorption of light results in an excited state of porphyrin molecules, and subsequent spin transfer from photoactive porphyrins to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals.
FDA Pharmacological Classification
585NM85KYM
METHYL AMINOLEVULINATE
Established Pharmacologic Class [EPC] - Porphyrin Precursor
Chemical Structure [CS] - Porphyrinogens
Methyl aminolevulinate is a Porphyrin Precursor.
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.
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Ergänzende Hinweise
DefinitionChEBI: The methyl ester of 5-aminolevulinic acid. A prodrug, it is metabolised to protoporphyrin IX, a photosensitizer, and is used in the photodynamic treatment of non-melanoma skin cancer (including basal cell carcinoma). Topical application (often as the hydro hloride salt) results in an accumulation of protoporphyrin IX in the skin lesions to which the cream has been applied. Subsequent illumination with red light results in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills t e tumour cells.
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