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CHEBI:724125 - methyl 5-aminolevulinate

ChEBI IDCHEBI:724125
ChEBI Namemethyl 5-aminolevulinate
Stars
DefinitionThe 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC6H11NO3
Net Charge0
Average Mass145.158
Monoisotopic Mass145.07389
SMILESCOC(=O)CCC(=O)CN
InChIInChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
InChIKeyYUUAYBAIHCDHHD-UHFFFAOYSA-N
Wikipedia
Roles Classification
Applications:
dermatologic drug  A drug used to treat or prevent skin disorders or for the routine care of skin.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
photosensitizing agent  A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
methyl 5-aminolevulinate (CHEBI:724125) has functional parent 5-aminolevulinic acid (CHEBI:17549)
methyl 5-aminolevulinate (CHEBI:724125) has role antineoplastic agent (CHEBI:35610)
methyl 5-aminolevulinate (CHEBI:724125) has role dermatologic drug (CHEBI:50177)
methyl 5-aminolevulinate (CHEBI:724125) has role photosensitizing agent (CHEBI:47868)
methyl 5-aminolevulinate (CHEBI:724125) has role prodrug (CHEBI:50266)
methyl 5-aminolevulinate (CHEBI:724125) is a δ-amino acid ester (CHEBI:60638)
Incoming Relation(s)
methyl 5-aminolevulinate hydrochloride (CHEBI:60641) has part methyl 5-aminolevulinate (CHEBI:724125)
IUPAC Name 
methyl 5-amino-4-oxopentanoate
Synonyms  Source
5-aminolevulinic acid methyl esterChemIDplus
aminolevulinic acid methyl esterChemIDplus
Methyl aminolevulinateChEMBL
methyl δ-aminolevulinateChEBI
Manual XrefsDatabases
168DrugCentral
D08204KEGG DRUG
DB00992DrugBank
Methyl_AminolevulinateWikipedia
Registry NumbersSources
Reaxys:5921212Reaxys
CAS:33320-16-0ChemIDplus
CAS:33320-16-0KEGG DRUG
Citations