Methyl Aminolevulinate
methyl 5-amino-4-oxopentanoate
Molecular Identity
Methyl Aminolevulinate
methyl 5-amino-4-oxopentanoate
PubChem CID: 157922
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.
2D Structure
Properties
C6H11NO3
Molecular Formula
145.16
Molecular Weight
g/mol
145.0739
Exact Mass
Da
-1
XLogP
Drug-like (Lipinski: < 5)
69.4
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
4
H-Bond Acceptors
133
Complexity
SMILES
Canonical SMILES
SMILES: COC(=O)CCC(=O)CNIsomeric SMILES
SMILES: COC(=O)CCC(=O)CNSynonyms(20)
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-aminolevulinateDTXSID3048570CHEBI:724125RefChem:157787
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Methyl Aminolevulinate
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