Methyl Aminolevulinate

HCID 157922CAS 33320-16-0

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

Methyl aminolevulinatemethyl 5-amino-4-oxopentanoate33320-16-0methyl 5-aminolevulinate5-Aminolevulinic acid methyl estermethyl aminolaevulinatemethyl delta-aminolevulinateMAOP cpdMethylaminolevulinatePentanoic acid, 5-amino-4-oxo-, methyl ester585NM85KYMMethyl-5-aminolevulinate
Weitere Namen anzeigen
D-AminolevulinicacidmethylesterHCl
DTXSID3048570CHEBI:724125RefChem:157787DTXCID4028202MetvixAminolevulinic acid methyl esterNCGC00018251-03UNII-585NM85KYM

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

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.2
Solubility · 2 Einträge

Freely soluble

2.20e+02 g/L

Physical DescriptionSolid

Physikochemische Eigenschaften

LogP
-0.57 · -0.570 (est)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

L01XD03

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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 · 5 Einträge

585NM85KYM

METHYL AMINOLEVULINATE

Established Pharmacologic Class [EPC] - Porphyrin Precursor

Chemical Structure [CS] - Porphyrinogens

Methyl aminolevulinate is a Porphyrin Precursor.

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.

Absorption, Distribution and ExcretionIn vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.

Anbieter11 Anbieter

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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.

Zugehörige Reaktionen

5

Verknüpfte Notizen

Wird geladen…