methyl 5-amino-4-oxopentanoate

• ChemBase ID: 866
• Molecular Formular: C6H11NO3
• Molecular Mass: 145.15644
• Monoisotopic Mass: 145.07389322
• SMILES: O(C(=O)CCC(=O)CN)C
• Canonical SMILES: NCC(=O)CCC(=O)OC
• InChI: InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
• InChIKey: YUUAYBAIHCDHHD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 5-amino-4-oxopentanoate
• IUPAC Traditional name: methyl aminolevulinate
• Brand Name: Metvix
• Synonyms: 5-Aminolevulinic acid methyl ester; Aminolevulinic acid methyl ester; Methyl aminolevulinate

Database IDs

• CAS Number: 33320-16-0
• PubChem SID: 46507004; 160964329
• PubChem CID: 157922

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.117233
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -3.1040556
• LogD (pH = 7.4): -1.416226
• Log P: -0.8470932
• Molar Refractivity: 35.2169 cm^3
• Polarizability: 14.204587 Å^3
• Polar Surface Area: 69.39 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.3
• LOG S: 0.18
• Solubility (Water): 2.20e+02 g/l

PROPERTIES

Physical Property

• Solubility: Freely soluble
• Hydrophobicity(logP): -1.2

DETAILS

DrugBank - DB00992

• Drug Groups: approved
• Description: Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.
• Indication: For topical use, in combination with 570 to 670 nm wavelength red light illumination, in the treatment of non-hyperkeratotic actinic keratoses of the face and scalp in immunocompetent patients when used in conjunction with lesion preparation (debridement using a sharp dermal curette).
• Pharmacology: After topical application of methyl aminolevulinate, porphyrins will accumulate intracellularly in the treated skin lesions. The intracellular porphyrins (including PpIX) are photoactive, fluorescing compounds and, upon light activation in the presence of oxygen, singlet oxygen is formed which causes damage to cellular compartments, in particular the mitochondria. Light activation of accumulated porphyrins leads to a photochemical reaction and thereby phototoxicity to the light-exposed target cells.
• Toxicity: The severity of local phototoxic reactions such as erythema, pain and burning sensation may increase in case of prolonged application time or very high light intensity.
• Affected Organisms: Humans and other mammals
• Absorption: In vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.
• References: [Link] ; Smits T, Moor AC: New aspects in photodynamic therapy of actinic keratoses. J Photochem Photobiol B. 2009 Sep 4;96(3):159-69. Epub 2009 Jun 13. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Link
• Smits T, Moor AC: New aspects in photodynamic therapy of actinic keratoses. J Photochem Photobiol B. 2009 Sep 4;96(3):159-69. Epub 2009 Jun 13. Pubmed