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Methyl aminolevulinate

CAT: 0804-HY-A0169Size: 1 EachDry Ice: NoHazardous: No
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Description
Methyl aminolevulinate is an agent used as a sensitizer in photodynamic therapy (PDT) . Methyl aminolevulinate is a proagent that can be metabolized to Protoporphyrin IX[1].
CAS Number
33320-16-0
UNSPSC
12352211
Hazard Statement
H315-H319-H320
Target
Reactive Oxygen Species (ROS)
Type
Reference compound
Related Pathways
Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/methyl-aminolevulinate.html
Solubility
10 mM in DMSO
Smiles
O=C(OC)CCC(CN)=O
Molecular Formula
C6H11NO3
Molecular Weight
145.16
Precautions
P264-P280-P302+P352-P305+P351+P338-P362
References & Citations
[1]Methyl aminolevulinate, From Wikipedia
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Methyl Aminolevulinate

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.

CAS Number33320-16-0
PubChem CID157922
IUPAC Namemethyl 5-amino-4-oxopentanoate
Molecular FormulaC6H11NO3
Molecular Weight145.16
XLogP-1
Topological Polar Surface Area69.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Heavy Atom Count10
Formal Charge0
Complexity133
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
Chemical Structure
2D Structure
2D structure of Methyl Aminolevulinate
CAS: 33320-16-0
CID: 157922
Formula: C6H11NO3
MW: 145.16
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight145.16
XLogP3-1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass145.07389321
Monoisotopic Mass145.07389321
Topological Polar Surface Area69.4 Ų
Heavy Atom Count10
Formal Charge0
Complexity133
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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RG-A262294-01Methyl Aminolevulinate
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