methyl 5-aminolevulinate (CHEBI:724125)

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:724125 - methyl 5-aminolevulinate

ChEBI ID	CHEBI:724125
ChEBI Name	methyl 5-aminolevulinate
Stars
Definition	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.
Last Modified	22 February 2017
Downloads	Molfile

Formula	C6H11NO3
Net Charge	0
Average Mass	145.158
Monoisotopic Mass	145.07389
SMILES	COC(=O)CCC(=O)CN
InChI	InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
InChIKey	YUUAYBAIHCDHHD-UHFFFAOYSA-N

Wikipedia

Roles Classification

Applications:

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.

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.

dermatologic drug A drug used to treat or prevent skin disorders or for the routine care of skin.

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)
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
Methyl aminolevulinate	ChEMBL
5-aminolevulinic acid methyl ester	ChemIDplus
aminolevulinic acid methyl ester	ChemIDplus
methyl δ-aminolevulinate	ChEBI

Manual Xrefs	Databases
D08204	KEGG DRUG
DB00992	DrugBank
Methyl_Aminolevulinate	Wikipedia
168	DrugCentral

Registry Numbers	Sources
Reaxys:5921212	Reaxys
CAS:33320-16-0	ChemIDplus
CAS:33320-16-0	KEGG DRUG

Citations