CHEBI:60641 - methyl 5-aminolevulinate hydrochloride

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ChEBI Name methyl 5-aminolevulinate hydrochloride
ChEBI ID CHEBI:60641
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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C6H12ClNO3
Net Charge 0
Average Mass 181.61700
Monoisotopic Mass 181.051
InChI InChI=1S/C6H11NO3.ClH/c1-10-6(9)3-2-5(8)4-7;/h2-4,7H2,1H3;1H
InChIKey UJYSYPVQHFNBML-UHFFFAOYSA-N
SMILES [Cl-].COC(=O)CCC(=O)C[NH3+]
Roles Classification
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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.
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ChEBI Ontology
Outgoing 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 Sources
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
methyl δ-aminolevulinate HCl ChEBI
methyl δ-aminolevulinate hydrochloride ChEBI
Manual Xref Database
D04988 KEGG DRUG
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Registry Numbers Types Sources
5991317 Reaxys Registry Number Reaxys
79416-27-6 CAS Registry Number ChemIDplus
Last Modified
15 November 2010