methyl 5-aminolevulinate hydrochloride (CHEBI:60641)

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CHEBI:60641 - methyl 5-aminolevulinate hydrochloride

ChEBI ID	CHEBI:60641
ChEBI Name	methyl 5-aminolevulinate hydrochloride
Stars
Definition	The hydrochloride salt of methyl 5-aminolevulinate. 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 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	15 November 2010
Submitter	Gareth Owen
Downloads	Molfile

Formula	C6H12NO3.Cl
Net Charge	0
Average Mass	181.619
Monoisotopic Mass	181.05057
SMILES	COC(=O)CCC(=O)C[NH3+].[Cl-]
InChI	InChI=1S/C6H11NO3.ClH/c1-10-6(9)3-2-5(8)4-7;/h2-4,7H2,1H3;1H
InChIKey	UJYSYPVQHFNBML-UHFFFAOYSA-N

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 hydrochloride (CHEBI:60641) has part methyl 5-aminolevulinate (CHEBI:724125)
	methyl 5-aminolevulinate hydrochloride (CHEBI:60641) has role antineoplastic agent (CHEBI:35610)
	methyl 5-aminolevulinate hydrochloride (CHEBI:60641) has role dermatologic drug (CHEBI:50177)
	methyl 5-aminolevulinate hydrochloride (CHEBI:60641) has role photosensitizing agent (CHEBI:47868)
	methyl 5-aminolevulinate hydrochloride (CHEBI:60641) has role prodrug (CHEBI:50266)
	methyl 5-aminolevulinate hydrochloride (CHEBI:60641) is a hydrochloride (CHEBI:36807)

IUPAC Name
5-methoxy-2,5-dioxopentan-1-aminium chloride

Synonyms	Source
methyl 5-amino-4-oxopentanoate hydrochloride	IUPAC
methyl 5-amino-4-oxovalerate HCl	ChEBI
methyl 5-amino-4-oxovalerate hydrochloride	ChemIDplus
methyl 5-aminolevulinate HCl	ChEBI
methyl aminolevulinate HCl	ChemIDplus
methyl aminolevulinate hydrochloride	ChemIDplus

Manual Xrefs	Databases
D04988	KEGG DRUG

Registry Numbers	Sources
Reaxys:5991317	Reaxys
CAS:79416-27-6	ChemIDplus