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methyl 5-aminolevulinate
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.


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05. Industrial Uses: pharmaceutical [CHEBI:52217] > drug [CHEBI:23888] > photosensitizing agent [CHEBI:47868] > methyl 5-aminolevulinate [CHEBI:724125]
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05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 antineoplastic agent [CHEBI:35610] (760) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
 photosensitizing agent [CHEBI:47868] (22) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
 dermatologic drug [CHEBI:50177] (49) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
 prodrug [CHEBI:50266] (88) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 delta-amino acid ester [CHEBI:60638] (1) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 delta-amino acid ester [CHEBI:60638] (1) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 delta-amino acid ester [CHEBI:60638] (1) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
 ester [CHEBI:35701] (3370) 
 carboxylic ester [CHEBI:33308] (1495) 
 delta-amino acid ester [CHEBI:60638] (1) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 delta-amino acid ester [CHEBI:60638] (1) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 organic molecule [CHEBI:72695] (11399) 
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 delta-amino acid ester [CHEBI:60638] (1) 
 methyl 5-aminolevulinate [CHEBI:724125] (1)
ChEBI Compound Accession Identifier  [CHEBI:724125]
ChEBI Compound Description  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.
ChEBI Compound Identification Number  724125
ChEBI InChI Value  InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
ChEBI InChIKey Value  YUUAYBAIHCDHHD-UHFFFAOYSA-N
ChEBI Compound Name  methyl 5-aminolevulinate
ChEBI SMILES Value  COC(=O)CCC(=O)CN
ChEBI Substance ID  99333768
ChEBI URL  ChEBI:724125
ChemSpider ID  138950
Ontomatica Chemical Accession Key (OnChAKey)  YUUAYBAIHCDHHD_UHFFFAOYSA_N_000_000000
PubChem Compound ID  157922